Coca-Cola formula

From Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Coca-Cola_formula 

 

The recipe for Coca-Cola remains a closely guarded trade secret.

 

The Coca-Cola Company's formula for Coca-Cola syrup, which bottlers combine with carbonated water to create the company's flagship cola soft drink, is a closely guarded trade secret. Company founder Asa Candler initiated the veil of secrecy that surrounds the formula in 1891 as a publicity, marketing, and intellectual property protection strategy. While several recipes, each purporting to be the authentic formula, have been published, the company maintains that the actual formula remains a secret, known only to a very few select (and anonymous) employees.

History

Vault containing the secret formula at the World of Coca-Cola in Atlanta

Coca-Cola inventor John Pemberton is known to have shared his original formula with at least four people before his death in 1888. In 1891, Asa Candler purchased the rights to the formula from Pemberton's estate, founded The Coca-Cola Company, and instituted the shroud of secrecy that has since enveloped the formula. He also made changes to the ingredients list, which by most accounts improved the flavor, and also entitled him to claim that anyone in possession of Pemberton's original formula no longer knew the "real" formula.

In 1919, Ernest Woodruff led a group of investors in purchasing the company from Candler and his family. As collateral for the acquisition loan, Woodruff placed the only written copy of the formula in a vault at the lending bank, Guaranty Bank in New York. In 1925, when the loan had been repaid, Woodruff relocated the written formula to the Trust Company Bank (now SunTrust Bank) in Atlanta. On December 8, 2011, the company placed it in a vault on the grounds of the World of Coca-Cola in Atlanta, where it remains on public "display".

According to the company, only two employees are privy to the complete formula at any given time and they are not permitted to travel together. When one dies, the other must choose a successor within the company and impart the secret to that person. The identity of the two employees in possession of the secret is itself a secret. It has been noted, however, that the company's "secret formula" policy is more of a marketing strategy than an actual trade secret: any competitor in possession of the genuine Coke recipe would be unable to obtain certain key ingredients, such as processed coca leaf (see below), and even if all components were available, could not market the reproduced product as Coca-Cola.

Coca leaves

During the late 19th century, Coca-Cola was one of many popular coca-based drinks with purported medicinal properties and benefits to health; early marketing materials claimed that Coca-Cola alleviated headaches and acted as a "brain and nerve tonic". Coca leaves were used in Coca-Cola's preparation; the small amount of cocaine they contained – along with caffeine originally sourced from kola nuts – provided the drink's "tonic" quality. In 1903, cocaine was removed, leaving caffeine as the sole stimulant ingredient, and all medicinal claims were dropped. By one account, the FDA still screens random samples of Coca-Cola syrup for the presence of cocaine.

A few sources claim that coca leaf extract, with the cocaine chemically removed, remains part of the formula as a flavoring. According to these accounts, the company obtains the ingredient from the Stepan Company of Maywood, New Jersey, which legally extracts cocaine from coca leaves for use in pharmaceuticals, then sells the processed leaf material for use in Coca Cola. The company will neither confirm nor deny this, deferring to the secret nature of the formula.

In 1911, the United States government sued The Coca-Cola Company for violations of the Pure Food and Drugs Act, claiming that the high concentration of caffeine in Coca-Cola syrup was harmful to health. The case was decided in favor of Coca-Cola, but a portion of the decision was set aside in 1916 by the Supreme Court. As part of a settlement, the company agreed to reduce the amount of caffeine in its syrup.

Current ingredients

The company protects the secrecy of its syrup recipe by shipping ingredients to its syrup factories in the form of anonymous "merchandises", numbered 1 through 9. Factory managers are told the relative proportions of each numbered merchandise, and the mixing procedure, but not the ingredients in the merchandises, some of which are themselves mixtures of more basic ingredients. Merchandise no. 1 is known to be sugar, in the form of high-fructose corn syrup or sucrose (see variations, below); caramel coloring is no. 2, caffeine is no. 3, and phosphoric acid is no. 4. The identities of merchandises 5 through 9 are a matter of debate – particularly "merchandise 7X" (the "X" has never been explained), which is thought to contain a mixture of essential oils such as orange, lime, and lemon. Another ingredient is thought to be lavender.

Despite the implications of its name, there is no evidence that the current version of Coca-Cola syrup contains kola nut extract, which was originally included for its caffeine content. The modern source of that additive is probably caffeine citrate, a byproduct of the decaffeination of coffee.

The primary taste of Coca-Cola is thought to come from vanilla and cinnamon, with trace amounts of essential oils, and spices such as nutmeg. A 2015 study identified and measured 58 aroma compounds in common colas, confirming significant amounts of compounds corresponding to cinnamon, vanilla, nutmeg, orange and lemon essential oils in Coca-Cola.

Formula variations in the United States

During the 1980s, most U.S. Coca-Cola bottlers switched their primary sweetening ingredient from cane sugar (sucrose) to the cheaper high-fructose corn syrup. The only U.S. bottler still using sucrose year-round is the Coca-Cola Bottling Company of Cleveland, which serves northern Ohio and a portion of Pennsylvania. Many bottlers outside the U.S. also continue to use sucrose as the primary sweetener. Twelve-ounce glass bottles of sucrose-sweetened Coca-Cola imported from Mexico are available in many U.S. markets for those consumers who prefer the sucrose version (see "Mexican Coke", below).

Passover

Coca-Cola was certified kosher in 1935 by Rabbi Tobias Geffen after beef tallow-derived glycerin was replaced with vegetable glycerin. However, the high-fructose corn syrup used by most U.S. bottlers since the 1980s renders it kitniyot by the definitions of Jewish kosher law, and therefore forbidden during Passover according to certain traditions. Each year, in the weeks leading up to Passover, bottlers in markets with substantial Jewish populations switch to sucrose sweetener in order to obtain Kosher for Passover certification.

"New Coke"

In April 1985, in response to marketing research suggesting that a majority of North American consumers preferred the taste of rival Pepsi to Coca-Cola, the company introduced a sweeter, less effervescent version of Coca-Cola in the U.S. and Canada. Although the new formulation had beaten both Pepsi-Cola and the old Coke formula in multiple blind taste tests, consumer response was overwhelmingly negative. The company quickly reintroduced the original beverage, rebranded as "Coca-Cola Classic", while continuing to market the new version as "Coke".

New Coke remained on the market, in North America only, for 17 years—the last 10 as "Coke II"—until it was quietly discontinued in 2002. The "Classic" designation remained on the original product's label, its prominence gradually decreasing over the years, until it was removed entirely in 2009.

Mexican Coke

In the early 2000s, cane-sugar-sweetened Coca-Cola produced in Mexico began to appear in bodegas and Hispanic supermarkets in the Southwestern United States; in 2005, Costco began offering it. All were obtaining the Mexican product—which was not labeled in accordance with U.S. food labeling laws—outside the official Coca-Cola distribution network. In 2009, the Coca-Cola Company began officially importing Coca-Cola produced in Mexico, with proper labeling, for distribution through official channels.

Purported secret recipes

Pemberton recipe

Coca-Cola inventor John Pemberton is said to have written this recipe in his diary shortly before his death in 1888. The recipe does not specify when or how the ingredients are mixed, nor the flavoring oil quantity units of measure (though it implies that the "Merchandise 7X" was mixed first). This was common in recipes at the time, as it was assumed that preparers knew the method.

• Ingredients:
• 1 oz (28 g) caffeine citrate
• 3 oz (85 g) citric acid
• 1 US fl oz (30 ml) vanilla extract
• 1 US qt (946 ml) lime juice
• 2.5 oz (71 g) "flavoring", i.e., "Merchandise 7X"
• 30 lb (14 kg) sugar
• 4 US fl oz (118.3 ml) fluid extract of coca leaves (flavor essence of the coca leaf).
• 2.5 US gal (9.5 l; 2.1 imp gal) water
• caramel sufficient to give color
• "Mix caffeine acid and lime juice in 1 quart boiling water add vanilla and flavoring when cool."
• Flavoring (Merchandise 7X):
• 1 qrt alcohol
• 80 oil orange
• 40 oil cinnamon
• 120 oil lemon
• 20 oil coriander
• 40 oil nutmeg
• 40 oil neroli
• "Let stand 24 hours."

Merory recipe

Recipe is from Food Flavorings: Composition, Manufacture and Use. Makes one 1 US gallon (3.8 l; 0.83 imp gal) of syrup. Yield (used to flavor carbonated water at 1 US fl oz (30 ml) per bottle): 128 bottles, 6.5 US fl oz (190 ml).

• Mix 5 lb (2.3 kg) of sugar with just enough water to dissolve the sugar fully. (High-fructose corn syrup may be substituted for half the sugar.)
• Add 1 ¹⁄₄ oz (35 g) of caramel, ¹⁄₁₀ oz (3 g) caffeine, and ²⁄₅ oz (11 g) phosphoric acid.
• Extract the cocaine from ⁵⁄₈ drachm (1.1 g) of coca leaf (Truxillo growth of coca preferred) with toluol; discard the cocaine extract.
• Soak the coca leaves and kola nuts (both finely powdered); ¹⁄₅ drachm (0.35 g) in ³⁄₄ oz (21 g) of 20% alcohol.
• California white wine fortified to 20% strength was used as the soaking solution circa 1909, but Coca-Cola may have switched to a simple water/alcohol mixture.
• After soaking, discard the coca and kola and add the liquid to the syrup.
• Add 1 oz (28 g) lime juice (a former ingredient, evidently, that Coca-Cola now denies) or a substitute such as a water solution of citric acid and sodium citrate at lime-juice strength.
• Mix together
• ¹⁄₄ drachm (0.44 g) orange oil,
• ¹⁄₁₀ drachm (0.18 g) cassia (Chinese cinnamon) oil,
• ¹⁄₂ drachm (0.89 g) lemon oil, traces of
• ²⁄₅ drachm (0.71 g) nutmeg oil, and, if desired, traces of
• coriander,
• neroli, and
• lavender oils.
• Add ¹⁄₁₀ oz (2.8 g) water to the oil mixture and let stand for twenty-four hours at about 60 °F (16 °C). A cloudy layer will separate.
• Take off the clear part of the liquid only and add to the syrup.
• Add ⁷⁄₁₀ oz (20 g) glycerine (from vegetable source, not hog fat, so the drink can be sold to Jews and Muslims who observe their respective religion's dietary restrictions) and ³⁄₁₀ drachm (0.53 g) of vanilla extract.
• Add water (treated with chlorine) to make a gallon of syrup.

Beal recipe

In 2011, Ira Glass announced on his Public Radio International show, This American Life, that show staffers had found a recipe in "Everett Beal's Recipe Book", reproduced in the February 28, 1979, issue of The Atlanta Journal-Constitution, that they believed was either Pemberton's original formula for Coca-Cola, or a version that he made either before or after the product was first sold in 1886. The formula is very similar to the one found in Pemberton's diary. Coca-Cola archivist Phil Mooney acknowledged that the recipe "could be a precursor" to the formula used in the original 1886 product, but emphasized that the original formula is not the same as the one used in the current product.

• Fluid extract of Coca: 3 drams USP
• Citric acid: 3 oz
• Caffeine: 1 oz
• Sugar: 30 lbs
• Water: 2.5 gal
• Lime juice: 2 pints (1 quart)
• Vanilla: 1 oz
• Caramel: 1.5 oz or more for color

The secret 7X flavor (use 2 oz of flavor to 5 gals syrup):

• Alcohol: 8 oz
• Orange oil: 20 drops
• Cinnamon oil: 10 drops
• Lemon oil: 30 drops
• Coriander oil: 5 drops
• Nutmeg oil: 10 drops
• Neroli oil: 10 drops

Commercial teaser

TV screen showing the ad formula

On January 23, 2011, in a commercial aired during the NFL Football AFC Championship Game, Coca-Cola teased that they would share the secret formula, only to flash a comical "formula" for a few frames. This required the use of a video recording device to freeze on the formula for any analysis, and it ultimately proved to be a marketing ploy with no intention of sharing the full official formula. Ingredients listed in the commercial included nutmeg oil, lime juice, cocoa, vanilla extract, caffeine, "flavoring", and a smile.

Grandfather clause

From Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Grandfather_clause 

 

A grandfather clause (or grandfather policy or grandfathering) is a provision in which an old rule continues to apply to some existing situations while a new rule will apply to all future cases. Those exempt from the new rule are said to have grandfather rights or acquired rights, or to have been grandfathered in. Frequently, the exemption is limited; it may extend for a set time, or it may be lost under certain circumstances. For example, a grandfathered power plant might be exempt from new, more restrictive pollution laws, but the exception may be revoked and the new rules would apply if the plant were expanded. Often, such a provision is used as a compromise or out of practicality, to allow new rules to be enacted without upsetting a well-established logistical or political situation. This extends the idea of a rule not being retroactively applied.

The term originated in late nineteenth-century legislation and constitutional amendments passed by a number of U.S. Southern states, which created new requirements for literacy tests, payment of poll taxes, and/or residency and property restrictions to register to vote. States in some cases exempted those whose ancestors (grandfathers) had the right to vote before the Civil War, or as of a particular date, from such requirements. The intent and effect of such rules was to prevent African-American former slaves and their descendants from voting, but without denying poor and illiterate whites the right to vote. Although these original grandfather clauses were eventually ruled unconstitutional, the terms grandfather clause and grandfather have been adapted to other uses.

Origin

The original grandfather clauses were contained in new state constitutions and Jim Crow laws passed between 1890 and 1908 by white-dominated state legislatures including Alabama, Georgia, Louisiana, North Carolina, Oklahoma, and Virginia. They restricted voter registration, effectively preventing African Americans from voting. Racial restrictions on voting in place before 1870 were nullified by the Fifteenth Amendment.

After Democrats took control of state legislatures again after the Compromise of 1877, they began to work to restrict the ability of blacks to vote. Paramilitary groups such as the White League, Red Shirts, and rifle clubs had intimidated blacks or barred them from the polls in numerous elections before what they called the Redemption (restoration of white supremacy). Nonetheless, a coalition of Populists and Republicans in fusion tickets in the 1880s and 1890s gained some seats and won some governor positions. To prevent such coalitions in the future, the Democrats wanted to exclude freedmen and other blacks from voting; in some states they also restricted poor whites to avoid biracial coalitions.

White Democrats developed statutes and passed new constitutions creating restrictive voter registration rules. Examples included imposition of poll taxes and residency and literacy tests. An exemption to such requirements was made for all persons allowed to vote before the American Civil War, and any of their descendants. The term grandfather clause arose from the fact that the laws tied the then-current generation's voting rights to those of their grandfathers. According to Black's Law Dictionary, some Southern states adopted constitutional provisions exempting from the literacy requirements descendants of those who fought in the army or navy of the United States or of the Confederate States during a time of war. 

After the U.S. Supreme Court found such provisions unconstitutional in Guinn v. United States (1915), states were forced to stop using the grandfather clauses to provide exemption to literacy tests. Without the grandfather clauses, tens of thousands of poor Southern whites were disenfranchised in the early 20th century. As decades passed, Southern states tended to expand the franchise for poor whites, but most blacks could not vote until after passage of the 1965 Voting Rights Act. Ratification in 1964 of the Twenty-fourth Amendment to the United States Constitution prohibited the use of poll taxes in federal elections, but some states continued to use them in state elections. 

The 1965 Voting Rights Act had provisions to protect voter registration and access to elections, with federal enforcement and supervision where necessary. In 1966, the Supreme Court ruled in Harper v. Virginia Board of Elections that poll taxes could not be used in any elections. This secured the franchise for most citizens, and voter registration and turnout climbed dramatically in Southern states.

There is also a rather different, older type of grandfather clause, perhaps more properly a grandfather principle in which a government blots out transactions of the recent past, usually those of a predecessor government. The modern analogue may be repudiating public debt, but the original was Henry II's principle, preserved in many of his judgments, "Let it be as it was on the day of my grandfather's death", a principle by which he repudiated all the royal grants that had been made in the previous 19 years under King Stephen.

Modern examples

Technology

• Most cellular phone carriers including AT&T and Verizon had an unlimited data plan in the past, but these plans were removed. Customers who already had unlimited data plans could continue to have them for as long as they kept the same service. For new subscribers, the unlimited plan was no longer available and they had to select from a limited plan (usually 2–4 GB) with extra charges and fees for going over the limit.
• Tablet computers (and similar devices) with screen sizes below eight inches which ran Windows 8 or Windows 8.1 featured a traditional Windows desktop with legacy app support, alongside the ability to run the newer Metro-style apps. However, newer devices with sub-8-inch screens that run the newly introduced Windows 10 operating system no longer have legacy app capability, and, as such, can only run apps downloaded from the Windows Store. Most (if not all) owners of the older Windows 8 devices of that screen size class who upgrade to Windows 10 can still retain the old-style desktop and legacy app support, despite this upgrade.
• Sirius XM Satellite Radio lifetime subscriptions are no longer being offered to new subscribers. Sirius XM Satellite Radio still honors lifetime subscriptions to people who have bought them in the past, under certain conditions.

Law

• Many jurisdictions prohibit ex post facto laws, and grandfather clauses can be used to prevent a law from having retroactive effects. For example, in the UK the offence of indecent assault is still charged in respect of crimes committed before the offence was abolished and replaced with sexual assault by the Sexual Offences Act 2003.
• Section 1 of Article Two of the United States Constitution appears on a cursory reading to stipulate that presidential candidates must be natural born citizens of the United States. However, there is a further category of persons eligible for that office, now exhausted: those who were citizens of the United States at the time of the adoption of that constitution. Without that provision, it would have required a strained reading to construe that all actual presidents born in the colonial era were born in the United States, because the United States did not exist prior to July 4, 1776, the date on which the Declaration of Independence was adopted.
• Many acts requiring registration to practice a particular profession incorporated transition or "grandfather sections" allowing those who had already practised for a specified time (often three or four years) to be registered under the act even if they did not have the training or qualifications required for new applications for registration. Examples are the Nurses Registration Act 1901 in New Zealand and the Nurses Registration Act 1919 in Britain.
• In 1949, standards were passed requiring certain fire-safety improvements in schools. However, older schools, such as the Our Lady of the Angels School in Illinois, were not required to be retrofitted to meet the requirements, leading to the deadly Our Lady of the Angels School fire in which 92 students and 3 teachers died.
• In 1951, the United States ratified the Twenty-second Amendment to the United States Constitution, preventing presidents from running for more than two full terms (or one full term, if they had served more than two years of another person's term). The text of the amendment specifically excluded the sitting president from its provisions, thus making Harry Truman eligible to run for president in 1952—and, theoretically, for every subsequent presidential election thereafter—even though he had served a full term and almost four years of a previous president's term. Truman was highly unpopular and lost the New Hampshire primary by nearly 55% to 44%. Eighteen days later the president announced he would not seek a second full term.
• In the 1980s, as states in America were increasing the permitted age of drinking to 21 years, many people who were under 21 but of legal drinking age before the change were still permitted to purchase and drink alcoholic beverages. Similar conditions applied when New Jersey and certain counties in New York raised tobacco purchase ages from 18 to 19 years in the early 2000s.
• In 2012, Macau increased the permitted age of entering casinos to 21. However, casino employees between the ages of 18 and 21 before the change were still permitted to enter their places of employment. This category was exhausted by the end of 2015.
• During the Federal Assault Weapons Ban, certain firearms made before the ban's enactment were legal to own. Automatic weapons that were manufactured and registered before the Firearm Owners Protection Act (enacted May 19, 1986) may legally be transferred to civilians.
• According to the Interstate Highway Act, private businesses are not allowed at rest areas along interstates. However, private businesses that began operations before January 1, 1960, were allowed to continue operation indefinitely.
• Michigan law MCL 287.1101–1123 forbade ownership or acquisition of large and dangerous exotic carnivores as pets. But animals already owned as pets at the time of enactment were grandfathered in, and permitted to be kept.
• The FCC stated that, as of March 1, 2007, all televisions must be equipped with digital tuners, but stores that had TV sets with analog tuners only could continue to sell analog-tuner TV sets.
• In 1967, the FCC prohibited companies from owning both a radio and a television station in the same marketing area, but those already owned before the ruling were permanently grandfathered. For example, ABC already owned WABC-TV, 77 WABC and WABC-FM (now WPLJ), and so could continue to own all three stations after the law was passed. But then-current broadcasting companies that had a radio station in a city could not acquire an adjacent television station, and companies that owned a television station in a city could not acquire adjacent radio stations. In 1996, the law was overturned. Companies can now own up to eight radio stations and two television stations in a market, provided that they do not receive more than 33% of that market's advertising revenues.
• In 1984 Mississippi passed a law changing its official mode of capital punishment from the gas chamber to lethal injection. Under the new law, anyone sentenced after July 1, 1984, was to be executed by lethal injection; those condemned before that date were “grandfathered” into the gas chamber. Therefore, three more convicted murderers would die in the chamber—Edward Earl Johnson and Connie Ray Evans in 1987, and Leo Edwards in 1989. In 1998, the Mississippi Legislature changed the execution law to allow all death row inmates to be executed by lethal injection.
• In 1965, the Canadian government under Prime Minister Lester B. Pearson passed legislation that required senators to retire when they reached the age of 75. However, senators appointed before the legislation was passed were exempted from the mandatory retirement rule.
• When Quebec enacted the Charter of the French Language in 1977, making French the province's official language, the famous Montreal kosher-style deli Schwartz's was allowed to keep its name with the apostrophe, a feature not used in French in the possessive form.
• During Canada's federal Redistribution, a grandfather clause ensures that no Province can have fewer seats after Redistribution than it did in 1985.
• In the early 2000s the Houston Police Department mandated to police academy graduating classes that tenured officers are required to carry a .40 caliber sidearm - tenured police officers prior to the mandate were grandfathered in where they still carried their existing sidearms.
• In 2013, Tennessee enacted a law requiring that products labeled as "Tennessee whiskey" be produced in the state, meet the legal definition of bourbon whiskey, and also use the Lincoln County Process. The law specifically allowed Benjamin Prichard's Tennessee Whiskey, which does not use the Lincoln County Process, to continue to be labeled as such.
• In 2014, Kentucky radically simplified its classification of cities, with the previous system of six population-based classes being replaced by a two-class system based solely on the type of government effective January 1, 2015. In the old classification system, many cities had special privileges (notably in alcoholic beverage control, taxing powers, certain labor laws, and the ability to operate its own school system) based on their class; the new legislation contained elaborate provisions to ensure that no city lost a privilege due to the reclassification.

Standards compliance

• Strict building codes to withstand frequent seismic activity were implemented in Japan in 1981. These codes applied only to new buildings, and existing buildings were not required to upgrade to meet the codes. One result of this was that during the great Kobe earthquake, many of the pre-1981 buildings were destroyed or written off, whereas most buildings built post-1981, in accordance with the new building codes, withstood the earthquake without structural damage.
• Wigwag-style railroad crossing signals were deemed inadequate in 1949 and new installations were banned in the United States. Existing wigwag signals were allowed to remain and 65 years later, there are still about 40 wigwag signals in use on railroads in the United States.
• The UK's national rail infrastructure management company Network Rail requires new locomotives and rolling stock to pass tests for electromagnetic compatibility (EMC) to ensure that they do not interfere with signalling equipment. Some old diesel locomotives, which have been in service for many years without causing such interference, are exempted from EMC tests and are said to have acquired grandfather rights.
• The Steel Electric-class ferryboats used by Washington State Ferries were in violation of several Coast Guard regulations, but because they were built in 1927, before the enactment of the regulations, they were allowed to sail. Those ferries were decommissioned in 2008.
• Tolled highways that existed before the Interstate Highway System are exempt from Interstate standards despite being designated as Interstate highways. Many such toll roads (particularly the Pennsylvania Turnpike) remain as such. However, tolled highways built since the Interstate system, such as the tolled section of PA Route 60 and PA Turnpike 576, must be built or upgraded to Interstate standards before receiving Interstate designation. Both highways are to be part of the Interstate system, with PA 60 now I-376 and PA Turnpike 576 to become I-576 in the near future. As well, U.S. Interstate Highway standards mandate a minimum 11-foot median; however, highways built before those standards have been grandfathered into the system. The Kansas Turnpike is the most notable example, as it has been retrofitted with a Jersey barrier along its entire 236-mile (380-km) length.
• The earliest Ontario 400-series highways and other expressways do not meet current standards, however it would be prohibitively expensive to immediately rebuild them all to updated guidelines, unless a reconstruction is warranted by safety concerns and traffic levels. As a result, substandard sections of freeways such as low overpasses and short acceleration/deceleration lanes are often retrofitted with guard rail, warning signage, lower speed limits, or lighting.
• The United States Federal Communications Commission has required all radio stations licensed in the United States since the 1930s to have four-letter call signs starting with a W (for stations east of the Mississippi River) or a K (for stations west of the Mississippi River). But stations with three-letter call signs and stations west of the Mississippi River starting with a W and east of the Mississippi River starting with a K—such as WRR in Dallas and WHB in Kansas City, plus KQV and KYW in Pennsylvania, all licensed before the 1930s—have been permitted to keep their call signs. In the western United States, KOA in Denver, KGA in Spokane, KEX in Portland, and KHJ and KFI in Los Angeles, among many others, have been permitted to keep their original or reassigned three-letter call signs. In addition, a new or existing station may adopt a three-letter call set if they have a sister radio or TV station in that market with those calls (examples include WJZ-FM Baltimore and WGY-FM Albany, New York). (Note that stations licensed in Louisiana and Minnesota, the two states with significant territory on both sides of the Mississippi, are allowed to use call signs starting with either W or K, regardless of their location with respect to the river.)
• In aviation, grandfather rights refers to the control that airlines exert over “slots” (that is, times allotted for access to runways). While the trend in airport management has been to reassert control over these slots, many airlines are able to retain their traditional rights based on current licences.
• In the UK, until 1992, holders of ordinary car driving licences were allowed to drive buses of any size, provided that the use was not commercial and that there was no element of "hire or reward" in the vehicles' use; in other words, no one was paying to be carried. The law was changed in 1992 so that all drivers of large buses had to hold a PCV (PSV) licence, but anyone who had driven large buses could apply for grandfather rights to carry on doing so.
• Some MOT test standards in the UK do not apply to vehicles first registered prior to the implementation of the legislation that introduced them. For example, vehicles first registered prior to January 1, 1973 are exempt from the requirement to use retro-reflective yellow/white vehicle registration plates and vehicles first registered prior to January 1, 1965 are exempt from seat belt standards/legislation unless they have been retrospectively fitted.
• In some U.S. states, the inspection/maintenance (I/M) programs for motor vehicle emission testing have a rolling chassis exemption, e.g. a motor vehicle model 25 years old or more is exempted from emission tests.

Sports

• In 1920, when Major League Baseball introduced the prohibition of the spitball, the league recognized that some professional pitchers had nearly built their careers on using the spitball. The league made an exception for 17 named players, who were permitted to throw spitballs for the rest of their careers. Burleigh Grimes threw the last legal spitball in 1934.
• Beginning in 1979, the National Hockey League required all players to wear helmets. Nevertheless, if a player had signed his first professional contract before this ruling, he was allowed to play without a helmet if he so desired. Craig MacTavish was the last player to do so, playing without a helmet up until his retirement in 1997, other notable players include Guy Lafleur and Rod Langway who retired in 1991 and 1993, respectively. A similar rule was passed for NHL officials for the 1988-89 season; any official who started his career before the ruling could also go helmet-less if they so desired. Kerry Fraser was the last referee who was not required to wear a helmet, until the ratification of the new NHL Officials Association collective bargaining agreement on March 21, 2006 required all remaining helmet-less officials to wear one. The NHL created a similar rule in 2013 requiring visors for players with fewer than 25 games' experience.
• Major League Baseball rule 1.16 requires players who were not in the major leagues before 1983 to wear a batting helmet with at least one earflap. The last player to wear a flapless helmet was the Florida Marlins' Tim Raines in 2002 (career began in 1979). The last player eligible to do so was Julio Franco in 2007 (career began in 1982), although he opted to use a flapped helmet.
• The NFL outlawed the one-bar facemask for the 2004 season but allowed existing users to continue to wear them (even though by that time, the mask had mostly fallen out of favor, save for a handful of kickers/punters). Scott Player was the last player to wear the one-bar facemask in 2007.
• For many decades, American League (AL) umpires working behind home plate used large, balloon-style chest protectors worn outside the shirt or coat, while their counterparts in the National League wore chest protectors inside the shirt or coat, more akin to those worn by catchers. In 1977, the AL ruled that all umpires entering the league that year and in the future had to wear the inside protector, although umpires already in the league who were using the outside protector could continue to do so. The last umpire to regularly wear the outside protector was Jerry Neudecker, who retired after the 1985 season. (Since 2000, Major League Baseball has used the same umpire crews for both leagues.)
• The National Football League (NFL) currently prohibits corporate ownership of teams. Ownership groups can have no more than 24 members, and at least one partner must hold a 30% ownership stake. The league has exempted the Green Bay Packers from this rule; the team has been owned by a publicly owned, nonprofit corporation since 1923, decades before the league's current ownership rules were put in place in the 1980s.
• Similarly, in association football the Deutsche Fußball Liga, which operates the Bundesliga and 2. Bundesliga, prohibits corporate ownership of more than 49% of teams and rebranding as well (see 50+1 rule). The Royal Dutch Football Association has a similar rule with regard to the Eredivisie. However, Bayer Leverkusen and PSV Eindhoven can maintain their property and names as they were founded in the first decades of the twentieth century by Bayer and Philips as their sport teams. Another Bundesliga side, VfL Wolfsburg, is allowed to remain under the ownership of Volkswagen as it was founded in 1945 as a club for VW workers.
• Three former venues in the National Hockey League—Chicago Stadium, Boston Garden and Buffalo Memorial Auditorium—had shorter-than-regulation ice surface, as their construction predated the regulation. The distance was taken out of the neutral zone. All three arenas were replaced by newer facilities by 1996. The regulation does not apply in many minor league venues, and in older minor league venues shorter than regulation, the distance was taken from neutral zones.
• Five schools that are members of NCAA Division III, a classification whose members are generally not allowed to offer athletic scholarships, are specifically allowed to award scholarships in one or two sports, with at most one for each sex. Each of these schools had a men's team that participated in the NCAA University Division, the predecessor to today's Division I, before the NCAA adopted its current three-division setup in 1973. (The NCAA did not award national championships in women's sports until 1980–81 in Division II and Division III, and 1981–82 in Division I.) Three other schools were formerly grandfathered, but have either moved their Division I sports to Division III or discontinued them entirely.
• In 2006, NASCAR passed a rule that required teams to field no more than four cars. Since Roush Racing had five cars, they could continue to field five cars until the end of 2009.
• Jackie Robinson's #42, which he wore when he broke Major League Baseball's 20th-century color line and throughout his Hall of Fame career with the Brooklyn Dodgers, is the subject of two such grandfather clauses.
  • In 1997, MLB prohibited all teams from issuing #42 in the future; current players wearing #42 were allowed to continue to do so. New York Yankees' closer Mariano Rivera was the last active player to be grandfathered in, wearing #42 until he retired after the 2013 season. However, since 2009, all uniformed personnel (players, managers, coaches, umpires) are required to wear #42 (without names) on Jackie Robinson Day.
  • In 2014, Robinson's alma mater of UCLA, where he played four sports from 1939 to 1941, retired #42 across its entire athletic program. (The men's basketball team had previously retired the number for Walt Hazzard.) Three athletes who were wearing the number at the time (in women's soccer, softball, and football) were allowed to continue wearing the number for the rest of their UCLA careers.
• The NFL introduced a numbering system for the 1973 season, requiring players to be numbered by position. Players who played in the NFL in 1972 and earlier were allowed to keep their old numbers if their number was outside of their range for their position, although New York Giants linebacker Brad Van Pelt wore number 10 despite entering the league in 1973 (Linebackers had to be numbered in the 50s at the time; since 1984 they may now wear numbers in the 50s or 90s. Van Pelt got away with it because he was the team's backup kicker his rookie season). The last player to be covered by the grandfather clause was Julius Adams, a defensive end (1971–1985, 1987) for the New England Patriots, who wore number 85 through the 1985 season. He wore a different number during a brief return two years later.
  • Similarly, the NFL also banned the use of the numbers 0 and 00 (both treated a single number) for uniforms around the same time, but players Jim Otto and Ken Burrough used the number throughout the 1970s.
• The National Hot Rod Association is enforcing a grandfather clause banning energy drink sponsors from entering the sport if they were not sponsoring cars as of April 24, 2008, pursuant to the five-year extension of its sponsorship with Coca-Cola, which is changing the title sponsorship from Powerade to Full Throttle Energy Drink.
• Even though tobacco advertising in car racing was banned, the Marlboro cigarette brand, owned by British American Tobacco in Canada, and Philip Morris International elsewhere, is grandfathered in to sponsoring a car in the F1 series on the agreement that the name is not shown in places that banned it.
• NASCAR allows some grandfathered sponsorships by energy drink brands in the top-level Monster Energy Cup Series, while rules prohibit new sponsors in that category. Similar policies with regard to telecommunications companies were in effect when the series was sponsored by Sprint. Additionally, some insurance company sponsorships were grandfathered in when the second-level series now known as the Xfinity Series was sponsored by Nationwide Insurance.
• In 2013, the Professional Bull Riders made it mandatory that all contestants at their events who were born on or after October 15, 1994 ride with helmets. Those born before that date were grandfathered in and permitted to ride with their cowboy hats if so desired.
• In August 2014, the Baseball Hall of Fame and the Baseball Writers' Association of America (BBWAA) announced changes to the Hall of Fame balloting process effective with the election for the Hall's induction class of 2015. The most significant change was reducing the time frame of eligibility for recently retired players from 15 years to 10. Three players on the 2015 BBWAA ballot who had appeared on more than 10 previous ballots—Don Mattingly, Lee Smith, and Alan Trammell—were exempted from this change, and remained eligible for 15 years (provided they received enough votes to stay on the ballot).
• In November 2015, Little League Baseball changed its age determination date from April 30 to August 31—a calendar date that falls after the completion of all of the organization's World Series tournaments—effective with the 2018 season. The rule was written so that players born between May 1 and August 31, 2005, who would otherwise have been denied their 12-year-old season in the flagship Little League division, would be counted as 12-year-olds in the 2018 season.
• In December 2016, French Rugby Federation (FFR) president Bernard Laporte announced that all future members of France national teams in rugby union and rugby sevens would be required to hold French passports. At the time, eligibility rules of World Rugby, the sport's international governing body, required only three years' residency for national team eligibility, and did not require citizenship. Players who had represented France prior to the FFR policy change remain eligible for national team selection.

Tannic acid

From Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Tannic_acid 

 

Tannic acid

Names
IUPAC name 1,2,3,4,6-penta-O-{3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}-D-glucopyranose
Systematic IUPAC name 2,3-dihydroxy-5-({[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis({3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)oxan-2-yl]methoxy}carbonyl)phenyl 3,4,5-trihydroxybenzoate
Other names Acidum tannicum Gallotannic acid Digallic acid Gallotannin Tannimum Quercitannin Oak bark tannin Quercotannic acid Querci-tannic acid Querco-tannic acid
Identifiers
CAS Number	1401-55-4
3D model (JSmol)	Interactive image
Beilstein Reference	8186386
ChEBI	CHEBI:75211
ChEMBL	ChEMBL506247
ChemSpider	17286569
ECHA InfoCard	100.014.321
IUPHAR/BPS	4319
KEGG	C13452
PubChem CID	16129878
UNII	28F9E0DJY6
CompTox Dashboard (EPA)	DTXSID2026076
InChI[show]
SMILES[show]
Properties
Chemical formula	C76H52O46
Molar mass	1701.19 g/mol
Density	2.12g/cm3
Melting point	decomposes above 200 °C
Solubility in water	2850 g/L or 250 g/L
Solubility	100 g/L in ethanol 1 g/L in glycerol and acetone insoluble in benzene, chloroform, diethyl ether, petroleum, carbon disulfide, carbon tetrachloride.
Acidity (pKa)	ca. 6
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

A bottle of tannic acid (water solution).

Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (pK_a around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C₇₆H₅₂O₄₆, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (Caesalpinia spinosa), gallnuts from Rhus semialata or Quercus infectoria or Sicilian sumac leaves (Rhus coriaria).

According to the definitions provided in external references such as international pharmacopoeia, Food Chemicals Codex and FAO-WHO tannic acid monograph only tannins sourced from the above-mentioned plants can be considered as tannic acid. Sometimes extracts from chestnut or oak wood are also described as tannic acid but this is an incorrect use of the term. It is a yellow to light brown amorphous powder; 2850 grams dissolves in one litre of water (1.7 moles per liter). 

While tannic acid is a specific type of tannin (plant polyphenol), the two terms are sometimes (incorrectly) used interchangeably. The long-standing misuse of the terms, and its inclusion in scholarly articles has compounded the confusion. This is particularly widespread in relation to green tea and black tea, both of which contain tannin but not tannic acid.

Tannic acid is not an appropriate standard for any type of tannin analysis because of its poorly defined composition.

Quercitannic and gallotannic acids

Quercitannic acid is one of the two forms of tannic acid found in oak bark and leaves. The other form is called gallotannic acid and is found in oak galls.

The quercitannic acid molecule is also present in quercitron, a yellow dye obtained from the bark of the Eastern black oak (Quercus velutina), a forest tree indigenous in North America. It is described as a yellowish-brown amorphous powder. 

In 1838, Jöns Jacob Berzelius wrote that quercitannate is used to dissolve morphine.

In 1865 in the fifth volume of "A dictionary of chemistry", Henry Watts wrote :

It exhibits with ferric salts the same reactions as gallotannic acid. It differs however from the latter in not being convertible into gallic acid, and not yielding pyrogallic acid by dry distillation. It is precipitated by sulfuric acid in red flocks. (Stenhouse, Ann. Ch. Pharm. xlv. 16.)
According to Rochleder (ibid lxiii. 202), the tannic acid of black tea is the same as that of oak-bark.

In 1880, Etti gave for it the molecular formula C₁₇H₁₆O₉. He described it as an unstable substance, having a tendency to give off water to form anhydrides (called phlobaphenes), one of which is called oak-red (C₃₄H₃₀O₁₇). For him, it was not a glycoside.

In Allen's "Commercial Organic Analysis", published in 1912, the formula given was C₁₉H₁₆O₁₀.

Other authors gave other molecular formulas like C₂₈H₂₆O₁₅, while another formula found is C₂₈H₂₄O₁₁.

According to Lowe, two forms of the principle exist – one soluble in water, of the formula C₂₈H₂₈O₁₄, and the other scarcely soluble, C₂₈H₂₄O₁₂. Both are changed by the loss of water into oak red, C₂₈H₂₂O₁₁.

Quercitannic acid was for a time a standard used to assess the phenolic content in spices, given as quercitannic acid equivalent.

In an interesting historical note, the inventor Edward G. Acheson (Inventor of Carborundum) discovered that gallotannic acid greatly improved the plasticity of clay. In his report of this discovery in 1904 he noted that the only known historical reference to the use of organic material added to clay is the use of straw mixed with clay described in the Bible, Exodus 1:11 and that the Egyptians must have been aware of his (re-)discovery. He stated "This explains why the straw was used and why the children of Israel were successful in substituting stubble for straw, a course that would hardly be possible, were the fibre of the straw depended upon as a bond feasible for the clay, but quite reasonable where the extract of the plant was used."

Uses

Tannins are a basic ingredient in the chemical staining of wood, and are already present in woods like oak, walnut, and mahogany. Tannic acid can be applied to woods low in tannin so chemical stains that require tannin content will react. The presence of tannins in the bark of redwood (Sequoia) is a strong natural defense against wildfire, decomposition, and infestation by certain insects such as termites. It is found in the seeds, bark, cones, and heartwood.

Tannic acid is a common mordant used in the dyeing process for cellulose fibers such as cotton, often combined with alum and/or iron. The tannin mordant should be done first as metal mordants combine well with the fiber-tannin complex. However this use has lost considerable interest.

Similarly tannic acid can also be used as an aftertreatment to improve wash fastness properties of acid dyed polyamide. It is also an alternative for fluorcarbon aftertreatments to impart anti-staining properties to polyamide yarn or carpets. However, due to economic considerations currently the only widespread use as textile auxiliary is the use as an agent to improve chlorine fastness, i.e. resistance against dye bleaching due to cleaning with hypochlorite solutions in high-end polyamide 6,6-based carpets and swimwear. It is, however, used in relatively small quantities for the activation of upholstery flock; this serves as an anti-static treatment.

Tannic acid is used in the conservation of ferrous (iron based) metal objects to passivate and inhibit corrosion. Tannic acid reacts with the corrosion products to form a more stable compound, thus preventing further corrosion from taking place. After treatment the tannic acid residue is generally left on the object so that if moisture reaches the surface the tannic acid will be rehydrated and prevent or slow any corrosion. Tannic acid treatment for conservation is very effective and widely used but it does have a significant visual effect on the object, turning the corrosion products black and any exposed metal dark blue. It should also be used with care on objects with copper alloy components as the tannic acid can have a slight etching effect on these metals.

Tannic acid is also found in commercially available iron/steel corrosion treatments, such as Hammerite Kurust.

Use in food

Use of tannic acid in food applications is widespread; significant amounts are used as process aids in beer clarification, aroma compound in soft drinks and juices. Also important are applications in the wine industry, where it finds use as a natural clarifying agent, colour stabilizer and taste enhancer.

In many parts of the world, such uses are permitted. In the United States, tannic acid is generally recognized as safe by the Food and Drug Administration.

According to EU directive 89/107/EEC tannic acid cannot be considered as a food additive and consequently does not hold an E number. Under directive 89/107/EEC tannic acid can be referred to as a food ingredient. The E-number E181 is sometimes incorrectly used to refer to tannic acid; this in fact refers to the INS number assigned to tannic acid under the FAO-WHO Codex Alimentarius system.

Uses as a medication

In conjunction with magnesium and sometimes activated charcoal, tannic acid was once used as a treatment for many toxic substances, such as strychnine, mushroom, and ptomaine poisonings in the late 19th and early 20th centuries.

The introduction of tannic acid treatment of severe burn injuries in the 1920s significantly reduced mortality rates. During World War I, tannic acid dressings were prescribed to treat "burns, whether caused by incendiary bombs, mustard gas, or lewisite. After the war this use was abandoned due to the development of more modern treatment regimens. 

Tannic acid is still used in pharmaceutical applications to produce albumin tannate which is used as an antidiarrheal agent. Tannic acid is also used to produce tannate salts of certain antihistamine and antitussive products to impart increased stability or slow release properties to the active pharmaceutical ingredient. Further to this, tannic acid is the principal but perhaps minimally effective ingredient in anti-allergy sprays.

Tannins have also been reported to exert many physiological effects, such as to accelerate blood clotting, reduce blood pressure, decrease the serum lipid level, produce liver necrosis, and modulate immunoresponses. This would explain common folklore such as that soaking feet in tannic acid (or strong tea) can treat or prevent blisters, foot odor and rough, dry feet.

Hazards

Tannic acid could cause potential health hazards such as damage to the eye, skin, respiratory tract, and gastrointestinal tract. It may cause irritation, redness, pain, blurred vision, and possible eye damage. When tannic acid is absorbed through the skin in harmful amounts, it may cause irritation, redness, and pain. Nausea, vomiting and diarrhoea are symptoms of tannic acid ingestion and prolonged exposure may cause liver damage. Upon inhalation, tannic acid may cause respiratory tract irritation.

Crocodilian coloration

Skin color in Crocodilia (crocodiles and alligators) is very dependent on water quality. Algae-laden waters produce greener skin, while tannic acid in the water from decay of leaves from overhanging trees (which produces some types of blackwater rivers) often produce darker skin in these animals.