Disaccharide

From Wikipedia, the free encyclopedia

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

 

Sucrose, a disaccharide formed from condensation of a molecule of glucose and a molecule of fructose

 

A disaccharide (also called a double sugar or bivose) is the sugar formed when two monosaccharides (simple sugars) are joined by glycosidic linkage. Like monosaccharides, disaccharides are soluble in water. Three common examples are sucrose, lactose, and maltose. 

Disaccharides are one of the four chemical groupings of carbohydrates (monosaccharides, disaccharides, oligosaccharides, and polysaccharides). The most common types of disaccharides—sucrose, lactose, and maltose—have 12 carbon atoms, with the general formula C₁₂H₂₂O₁₁. The differences in these disaccharides are due to atomic arrangements within the molecule.

The joining of simple sugars into a double sugar happens by a condensation reaction, which involves the elimination of a water molecule from the functional groups only. Breaking apart a double sugar into its two simple sugars is accomplished by hydrolysis with the help of a type of enzyme called a disaccharidase. As building the larger sugar ejects a water molecule, breaking it down consumes a water molecule. These reactions are vital in metabolism. Each disaccharide is broken down with the help of a corresponding disaccharidase (sucrase, lactase, and maltase).

Classification

There are two functionally different classes of disaccharides:

• Reducing disaccharides, in which one monosaccharide, the reducing sugar of the pair, still has a free hemiacetal unit that can perform as a reducing aldehyde group; lactose, maltose and cellobiose are examples of reducing disaccharides, each with one hemiacetal unit, the other occupied by the glycosidic bond, which prevents it from acting as a reducing agent. They can easily be detected by the Woehlk test or Fearon's test on methylamine.
• Non-reducing disaccharides, in which the component monosaccharides bond through an acetal linkage between their anomeric centers. This results in neither monosaccharide being left with a hemiacetal unit that is free to act as a reducing agent. Sucrose and trehalose are examples of non-reducing disaccharides because their glycosidic bond is between their respective hemiacetal carbon atoms. The reduced chemical reactivity of the non-reducing sugars in comparison to reducing sugars, may be an advantage where stability in storage is important.

Formation

The formation of a disaccharide molecule from two monosaccharide molecules proceeds by displacing a hydroxyl radical from one molecule and a hydrogen nucleus (a proton) from the other, so that the now vacant bonds on the monosaccharides join the two monomers together. The vacant bonds on the hydroxyl radical and the proton unite in their turn, forming a molecule of water, that then goes free. Because of the removal of the water molecule from the product, the term of convenience for such a process is "dehydration reaction" (also "condensation reaction" or "dehydration synthesis"). For example, milk sugar (lactose) is a disaccharide made by condensation of one molecule of each of the monosaccharides glucose and galactose, whereas the disaccharide sucrose in sugar cane and sugar beet, is a condensation product of glucose and fructose. Maltose, another common disaccharide, is condensed from two glucose molecules.

The dehydration reaction that bonds monosaccharides into disaccharides (and also bonds monosaccharides into more complex polysaccharides) forms what are called glycosidic bonds.

Properties

The glycosidic bond can be formed between any hydroxyl group on the component monosaccharide. So, even if both component sugars are the same (e.g., glucose), different bond combinations (regiochemistry) and stereochemistry (alpha- or beta-) result in disaccharides that are diastereoisomers with different chemical and physical properties. 

Depending on the monosaccharide constituents, disaccharides are sometimes crystalline, sometimes water-soluble, and sometimes sweet-tasting and sticky-feeling.

Assimilation

Digestion involves breakdown to the monosaccharides.

Common disaccharides

Disaccharide	Unit 1	Unit 2	Bond
Sucrose (table sugar, cane sugar, beet sugar, or saccharose)	Glucose	Fructose	α(1→2)β
Lactose (milk sugar)	Galactose	Glucose	β(1→4)
Maltose (malt sugar)	Glucose	Glucose	α(1→4)
Trehalose	Glucose	Glucose	α(1→1)α
Cellobiose	Glucose	Glucose	β(1→4)
Chitobiose	Glucosamine	Glucosamine	β(1→4)

Maltose, cellobiose, and chitobiose are hydrolysis products of the polysaccharides starch, cellulose, and chitin, respectively.

Less common disaccharides include:

Disaccharide	Units	Bond
Kojibiose	two glucose monomers	α(1→2)
Nigerose	two glucose monomers	α(1→3)
Isomaltose	two glucose monomers	α(1→6)
β,β-Trehalose	two glucose monomers	β(1→1)β
α,β-Trehalose	two glucose monomers	α(1→1)β[11]
Sophorose	two glucose monomers	β(1→2)
Laminaribiose	two glucose monomers	β(1→3)
Gentiobiose	two glucose monomers	β(1→6)
Trehalulose	a glucose monomer and a fructose monomer	α(1→1)
Turanose	a glucose monomer and a fructose monomer	α(1→3)
Maltulose	a glucose monomer and a fructose monomer	α(1→4)
Leucrose	a glucose monomer and a fructose monomer	α(1→5)
Isomaltulose	a glucose monomer and a fructose monomer	α(1→6)
Gentiobiulose	a glucose monomer and a fructose monomer	β(1→6)
Mannobiose	two mannose monomers	either α(1→2), α(1→3), α(1→4), or α(1→6)
Melibiose	a galactose monomer and a glucose monomer	α(1→6)
Melibiulose	a galactose monomer and a fructose monomer	α(1→6)
Rutinose	a rhamnose monomer and a glucose monomer	α(1→6)
Rutinulose	a rhamnose monomer and a fructose monomer	β(1→6)
Xylobiose	two xylopyranose monomers	β(1→4)

Monosaccharide

From Wikipedia, the free encyclopedia

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

Monosaccharides (from Greek monos: single, sacchar: sugar), also called simple sugar, are the simplest form of sugar and the most basic units of carbohydrates. They cannot be further hydrolyzed to simpler chemical compounds. The general formula is C
_nH
_2nO
_n. They are usually colorless, water-soluble, and crystalline solids. Some monosaccharides have a sweet taste. But all the compounds which fit into this general formula may not be classified as carbohydrates. For example, Acetic Acid which fits in the formula is not a carbohydrate.

Examples of monosaccharides include glucose (dextrose), fructose (levulose), and galactose. Monosaccharides are the building blocks of disaccharides (such as sucrose and lactose) and polysaccharides (such as cellulose and starch). Each carbon atom that supports a hydroxyl group is chiral, except those at the end of the chain. This gives rise to a number of isomeric forms, all with the same chemical formula. For instance, galactose and glucose are both aldohexoses, but have different physical structures and chemical properties.

The monosaccharide glucose plays a pivotal role in metabolism, where the chemical energy is extracted through glycolysis and the citric acid cycle to provide energy to living organisms. Some other monosaccharides can be converted in the living organism to glucose.

Structure and nomenclature

With few exceptions (e.g., deoxyribose), monosaccharides have this chemical formula: (CH₂O)_x, where conventionally x ≥ 3. Monosaccharides can be classified by the number x of carbon atoms they contain: triose (3), tetrose (4), pentose (5), hexose (6), heptose (7), and so on. 

Glucose, used as an energy source and for the synthesis of starch, glycogen and cellulose, is a hexose. Ribose and deoxyribose (in RNA and DNA respectively) are pentose sugars. Examples of heptoses include the ketoses, mannoheptulose and sedoheptulose. Monosaccharides with eight or more carbons are rarely observed as they are quite unstable. In aqueous solutions monosaccharides exist as rings if they have more than four carbons.

Linear-chain monosaccharides

Simple monosaccharides have a linear and unbranched carbon skeleton with one carbonyl (C=O) functional group, and one hydroxyl (OH) group on each of the remaining carbon atoms. Therefore, the molecular structure of a simple monosaccharide can be written as H(CHOH)_n(C=O)(CHOH)_mH, where n + 1 + m = x; so that its elemental formula is C_xH_2xO_x. 

By convention, the carbon atoms are numbered from 1 to x along the backbone, starting from the end that is closest to the C=O group. Monosaccharides are the simplest units of carbohydrates and the simplest form of sugar. 

If the carbonyl is at position 1 (that is, n or m is zero), the molecule begins with a formyl group H(C=O)− and is technically an aldehyde. In that case, the compound is termed an aldose. Otherwise, the molecule has a keto group, a carbonyl −(C=O)− between two carbons; then it is formally a ketone, and is termed a ketose. Ketoses of biological interest usually have the carbonyl at position 2.

The various classifications above can be combined, resulting in names such as "aldohexose" and "ketotriose". 

A more general nomenclature for open-chain monosaccharides combines a Greek prefix to indicate the number of carbons (tri-, tetr-, pent-, hex-, etc.) with the suffixes "-ose" for aldoses and "-ulose" for ketoses. In the latter case, if the carbonyl is not at position 2, its position is then indicated by a numeric infix. So, for example, H(C=O)(CHOH)₄H is pentose, H(CHOH)(C=O)(CHOH)₃H is pentulose, and H(CHOH)₂(C=O)(CHOH)₂H is pent-3-ulose.

Open-chain stereoisomers

Two monosaccharides with equivalent molecular graphs (same chain length and same carbonyl position) may still be distinct stereoisomers, whose molecules differ in spatial orientation. This happens only if the molecule contains a stereogenic center, specifically a carbon atom that is chiral (connected to four distinct molecular sub-structures). Those four bonds can have any of two configurations in space distinguished by their handedness. In a simple open-chain monosaccharide, every carbon is chiral except the first and the last atoms of the chain, and (in ketoses) the carbon with the keto group.

For example, the triketose H(CHOH)(C=O)(CHOH)H (glycerone, dihydroxyacetone) has no stereogenic center, and therefore exists as a single stereoisomer. The other triose, the aldose H(C=O)(CHOH)₂H (glyceraldehyde), has one chiral carbon — the central one, number 2 — which is bonded to groups −H, −OH, −C(OH)H₂, and −(C=O)H. Therefore, it exists as two stereoisomers whose molecules are mirror images of each other (like a left and a right glove). Monosaccharides with four or more carbons may contain multiple chiral carbons, so they typically have more than two stereoisomers. The number of distinct stereoisomers with the same diagram is bounded by 2^c, where c is the total number of chiral carbons.

The Fischer projection is a systematic way of drawing the skeletal formula of an acyclic monosaccharide so that the handedness of each chiral carbon is well specified. Each stereoisomer of a simple open-chain monosaccharide can be identified by the positions (right or left) in the Fischer diagram of the chiral hydroxyls (the hydroxyls attached to the chiral carbons).

Most stereoisomers are themselves chiral (distinct from their mirror images). In the Fischer projection, two mirror-image isomers differ by having the positions of all chiral hydroxyls reversed right-to-left. Mirror-image isomers are chemically identical in non-chiral environments, but usually have very different biochemical properties and occurrences in nature. 

While most stereoisomers can be arranged in pairs of mirror-image forms, there are some non-chiral stereoisomers that are identical to their mirror images, in spite of having chiral centers. This happens whenever the molecular graph is symmetrical, as in the 3-ketopentoses H(CHOH)₂(CO)(CHOH)₂H, and the two halves are mirror images of each other. In that case, mirroring is equivalent to a half-turn rotation. For this reason, there are only three distinct 3-ketopentose stereoisomers, even though the molecule has two chiral carbons.

Distinct stereoisomers that are not mirror-images of each other usually have different chemical properties, even in non-chiral environments. Therefore, each mirror pair and each non-chiral stereoisomer may be given a specific monosaccharide name. For example, there are 16 distinct aldohexose stereoisomers, but the name "glucose" means a specific pair of mirror-image aldohexoses. In the Fischer projection, one of the two glucose isomers has the hydroxyl at left on C3, and at right on C4 and C5; while the other isomer has the reversed pattern. These specific monosaccharide names have conventional three-letter abbreviations, like "Glu" for glucose and "Thr" for threose.

Generally, a monosaccharide with n asymmetrical carbons has 2ⁿ stereoisomers. The number of open chain stereoisomers for an aldose monosaccharide is larger by one than that of a ketose monosaccharide of the same length. Every ketose will have 2⁽ⁿ⁻³⁾ stereoisomers where n > 2 is the number of carbons. Every aldose will have 2⁽ⁿ⁻²⁾ stereoisomers where n > 2 is the number of carbons. These are also referred to as epimers which have the different arrangement of −OH and −H groups at the asymmetric or chiral carbon atoms (this does not apply to those carbons having the carbonyl functional group).

Configuration of monosaccharides

Like many chiral molecules, the two stereoisomers of glyceraldehyde will gradually rotate the polarization direction of linearly polarized light as it passes through it, even in solution. The two stereoisomers are identified with the prefixes D- and L-, according to the sense of rotation: D-glyceraldehyde is dextrorotatory (rotates the polarization axis clockwise), while L-glyceraldehyde is levorotatory (rotates it counterclockwise).

D- and L-glucose

The D- and L- prefixes are also used with other monosaccharides, to distinguish two particular stereoisomers that are mirror-images of each other. For this purpose, one considers the chiral carbon that is furthest removed from the C=O group. Its four bonds must connect to −H, −OH, −C(OH)H, and the rest of the molecule. If the molecule can be rotated in space so that the directions of those four groups match those of the analog groups in D-glyceraldehyde's C2, then the isomer receives the D- prefix. Otherwise, it receives the L- prefix.

In the Fischer projection, the D- and L- prefixes specifies the configuration at the carbon atom that is second from bottom: D- if the hydroxyl is on the right side, and L- if it is on the left side.

Note that the D- and L- prefixes do not indicate the direction of rotation of polarized light, which is a combined effect of the arrangement at all chiral centers. However, the two enantiomers will always rotate the light in opposite directions, by the same amount. See also D/L system.

Cyclisation of monosaccharides

A monosaccharide often switches from the acyclic (open-chain) form to a cyclic form, through a nucleophilic addition reaction between the carbonyl group and one of the hydroxyls of the same molecule. The reaction creates a ring of carbon atoms closed by one bridging oxygen atom. The resulting molecule has a hemiacetal or hemiketal group, depending on whether the linear form was an aldose or a ketose. The reaction is easily reversed, yielding the original open-chain form.

In these cyclic forms, the ring usually has five or six atoms. These forms are called furanoses and pyranoses, respectively — by analogy with furan and pyran, the simplest compounds with the same carbon-oxygen ring (although they lack the double bonds of these two molecules). For example, the aldohexose glucose may form a hemiacetal linkage between the hydroxyl on carbon 1 and the oxygen on carbon 4, yielding a molecule with a 5-membered ring, called glucofuranose. The same reaction can take place between carbons 1 and 5 to form a molecule with a 6-membered ring, called glucopyranose. Cyclic forms with a seven-atom ring (the same of oxepane), rarely encountered, are called heptoses.

Conversion between the furanose, acyclic, and pyranose forms of D-glucose

Pyranose forms of some pentose sugars

Pyranose forms of some hexose sugars

For many monosaccharides (including glucose), the cyclic forms predominate, in the solid state and in solutions, and therefore the same name commonly is used for the open- and closed-chain isomers. Thus, for example, the term "glucose" may signify glucofuranose, glucopyranose, the open-chain form, or a mixture of the three.

Cyclization creates a new stereogenic center at the carbonyl-bearing carbon. The −OH group that replaces the carbonyl's oxygen may end up in two distinct positions relative to the ring's midplane. Thus each open-chain monosaccharide yields two cyclic isomers (anomers), denoted by the prefixes α- and β-. The molecule can change between these two forms by a process called mutarotation, that consists in a reversal of the ring-forming reaction followed by another ring formation.

Haworth projection

The stereochemical structure of a cyclic monosaccharide can be represented in a Haworth projection. In this diagram, the α-isomer for the pyranose form of a D-aldohexose has the −OH of the anomeric carbon below the plane of the carbon atoms, while the β-isomer has the −OH of the anomeric carbon above the plane. Pyranoses typically adopt a chair conformation, similar to that of cyclohexane. In this conformation, the α-isomer has the −OH of the anomeric carbon in an axial position, whereas the β-isomer has the −OH of the anomeric carbon in equatorial position (considering D-aldohexose sugars).

• 

  α-D-Glucopyranose
  
  
• 

  β-D-Glucopyranose
  
  

Derivatives

A large number of biologically important modified monosaccharides exist:

• Amino sugars such as:
  • galactosamine
  • glucosamine
  • sialic acid
  • N-acetylglucosamine
• Sulfosugars such as:
  • sulfoquinovose
• Others such as:
  • ascorbic acid
  • mannitol
  • glucuronic acid

High-fructose corn syrup

From Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/High-fructose_corn_syrup 

 

Structural formulae of fructose (left) and glucose (right)

High-fructose corn syrup (HFCS), also known as glucose-fructose, isoglucose and glucose-fructose syrup, is a sweetener made from corn starch. As in the production of conventional corn syrup, the starch is broken down into glucose by enzymes. To make HFCS, the corn syrup is further processed by glucose isomerase to convert some of its glucose into fructose. HFCS was first marketed in the early 1970s by the Clinton Corn Processing Company, together with the Japanese Agency of Industrial Science and Technology, where the enzyme was discovered in 1965.

As a sweetener, HFCS is often compared to granulated sugar, but manufacturing advantages of HFCS over sugar include that it is easier to handle and more cost-effective. "HFCS 42" and "HFCS 55" refer to 42% and 55% fructose composition respectively, the rest being glucose and water. HFCS 42 is mainly used for processed foods and breakfast cereals, whereas HFCS 55 is used mostly for production of soft drinks.

The United States Food and Drug Administration states that HFCS is a safe ingredient for food and beverage manufacturing. Uses and exports of HFCS from American producers have grown steadily during the early 21st century.

Food

In the U.S., HFCS is among the sweeteners that mostly replaced sucrose (table sugar) in the food industry. Factors contributing to the rise of HFCS include production quotas of domestic sugar, import tariffs on foreign sugar, and subsidies of U.S. corn, raising the price of sucrose and lowering that of HFCS, making it cheapest for many sweetener applications. In spite of having a 10% greater fructose content, the relative sweetness of HFCS 55, used most commonly in soft drinks, is comparable to that of sucrose. HFCS (and/or standard corn syrup) is the primary ingredient in most brands of commercial "pancake syrup", as a less expensive substitute for maple syrup.

Because of its similar sugar profile and lower price, HFCS is often added to adulterate honey. Assays to detect adulteration with HFCS use differential scanning calorimetry and other advanced testing methods.

Production

Process

In the contemporary process, corn is milled to extract corn starch and an "acid-enzyme" process is used, in which the corn-starch solution is acidified to begin breaking up the existing carbohydrates. High-temperature enzymes are added to further metabolize the starch and convert the resulting sugars to fructose. The first enzyme added is alpha-amylase, which breaks the long chains down into shorter sugar chains – oligosaccharides. Glucoamylase is mixed in and converts them to glucose. The resulting solution is filtered to remove protein, then using activated carbon, and then demineralized using ion-exchange resins. The purified solution is then run over immobilized xylose isomerase, which turns the sugars to ~50–52% glucose with some unconverted oligosaccharides and 42% fructose (HFCS 42), and again demineralized and again purified using activated carbon. Some is processed into HFCS 90 by liquid chromatography, and then mixed with HFCS 42 to form HFCS 55. The enzymes used in the process are made by microbial fermentation.

Composition and varieties

HFCS is 24% water, the rest being mainly fructose and glucose with 0–5% unprocessed glucose oligomers.

The most common forms of HFCS used for food and beverage manufacturing contain fructose in either 42% ("HFCS 42") or 55% ("HFCS 55") amounts, as described in the US Code of Federal Regulations (21 CFR 184.1866).

• HFCS 42 (approx. 42% fructose if water were ignored) is used in beverages, processed foods, cereals, and baked goods.
• HFCS 55 is mostly used in soft drinks.
• HFCS 65 is used in soft drinks dispensed by Coca-Cola Freestyle machines.
• HFCS 70 is used in filling jellies
• HFCS 90 has some niche uses,  but is mainly mixed with HFCS 42 to make HFCS 55.

Commerce and consumption

Consumption of sugar and corn-based sweeteners in the United States from 1966 to 2013, in dry-basis pounds per capita

The global market for HFCS is expected to grow from $5.9 billion in 2019 to a projected $7.6 billion in 2024.

China

HFCS in China makes up about 20% of sweetener demand. HFCS has gained popularity due to rising prices of sucrose, while selling for a third the price. Production was estimated to reach 4,150,000 tonnes in 2017. About half of total produced HFCS is exported to the Philippines, Indonesia, Vietnam, and India.

European Union

In the European Union (EU), HFCS is known as isoglucose or glucose-fructose syrup (GFS) which has 20–30% fructose content compared to 42% (HFCS 42) and 55% (HFCS 55) in the United States. While HFCS is produced exclusively with corn in the US, manufacturers in the EU use corn and wheat to produce GFS. GFS was once subject to a sugar production quota, which was abolished on 1 October 2017, removing the previous production cap of 720,000 tonnes, and allowing production and export without restriction. Use of GFS in soft drinks is limited in the EU because manufacturers do not have a sufficient supply of GFS containing at least 42% fructose content. As a result, soft drinks are primarily sweetened by sucrose which has a 50% fructose content.

Japan

In Japan, HFCS is also referred to as isomerized sugar. HFCS production arose in Japan after government policies created a rise in the price of sugar. Japanese HFCS is manufactured mostly from imported U.S. corn, and the output is regulated by the government. For the period from 2007 to 2012, HFCS had a 27–30% share of the Japanese sweetener market. Japan consumed approximately 800,000 tonnes of HFCS in 2016. The United States Department of Agriculture states that corn from the United States is what Japan uses to produce their HFCS. Japan imports at a level of 3 million tonnes per year, leading 20 percent of corn imports to be for HFCS production.

Mexico

Mexico is the largest importer of U.S. HFCS. HFCS accounts for about 27 percent of total sweetener consumption, with Mexico importing 983,069 tonnes of HFCS in 2018. Mexico's soft drink industry is shifting from sugar to HFCS which is expected to boost U.S. HFCS exports to Mexico according to a U.S. Department of Agriculture Foreign Agricultural Service report.

On 1 January 2002, Mexico imposed a 20% beverage tax on soft drinks and syrups not sweetened with cane sugar. The United States challenged the tax, appealing to the World Trade Organization (WTO). On 3 March 2006, the WTO ruled in favor of the U.S. citing the tax as discriminatory against U.S. imports of HFCS without being justified under WTO rules.

Philippines

The Philippines was the largest importer of Chinese HFCS. Imports of HFCS would peak at 373,137 tonnes in 2016. Complaints from domestic sugar producers would result in a crackdown on Chinese exports. On 1 January 2018, the Philippine government imposed a tax of 12 pesos ($.24) on drinks sweetened with HFCS versus 6 pesos ($.12) for drinks sweetened with other sugars.

United States

In the United States, HFCS was widely used in food manufacturing from the 1970s through the early 21st century, primarily as a replacement for sucrose because its sweetness was similar to sucrose, it improved manufacturing quality, was easier to use, and was cheaper. Domestic production of HFCS increased from 2.2 million tons in 1980 to a peak of 9.5 million tons in 1999. Although HFCS use is about the same as sucrose use in the United States, more than 90% of sweeteners used in global manufacturing is sucrose.

Production of HFCS in the United States was 8.3 million tons in 2017. HFCS is easier to handle than granulated sucrose, although some sucrose is transported as solution. Unlike sucrose, HFCS cannot be hydrolyzed, but the free fructose in HFCS may produce hydroxymethylfurfural when stored at high temperatures; these differences are most prominent in acidic beverages. Soft drink makers such as Coca-Cola and Pepsi continue to use sugar in other nations but transitioned to HFCS for U.S. markets in 1980 before completely switching over in 1984. Large corporations, such as Archer Daniels Midland, lobby for the continuation of government corn subsidies.

Consumption of HFCS in the U.S. has declined since it peaked at 37.5 lb (17.0 kg) per person in 1999. The average American consumed approximately 22.1 lb (10.0 kg) of HFCS in 2018, versus 40.3 lb (18.3 kg) of refined cane and beet sugar. This decrease in domestic consumption of HFCS resulted in a push in exporting of the product. In 2014, exports of HFCS were valued at $436 million, a decrease of 21% in one year, with Mexico receiving about 75% of the export volume.

In 2010, the Corn Refiners Association petitioned the FDA to call HFCS "corn sugar", but the petition was denied.

Vietnam

90% of Vietnam's HFCS import comes from China and South Korea. Imports would total 89,343 tonnes in 2017. One ton of HFCS was priced at $398 in 2017, while one ton of sugar would cost $702. HFCS has a zero cent import tax and no quota, while sugarcane under quota has a 5% tax, and white and raw sugar not under quota have an 85% and 80% tax. In 2018, the Vietnam Sugarcane and Sugar Association (VSSA) called for government intervention on current tax policies. According to the VSSA, sugar companies face tighter lending policies which cause the association's member companies with increased risk of bankruptcy.

Health

High-fructose corn syrup

Nutritional value per 100 g (3.5 oz)
Energy	1,176 kJ (281 kcal)
Carbohydrates	76 g
Dietary fiber	0 g
Fat	0 g
Protein	0 g
Vitamins	Quantity %DV†
Riboflavin (B2)	2% 0.019 mg
Niacin (B3)	0% 0 mg
Pantothenic acid (B5)	0% 0.011 mg
Vitamin B6	2% 0.024 mg
Folate (B9)	0% 0 μg
Vitamin C	0% 0 mg
Minerals	Quantity %DV†
Calcium	1% 6 mg
Iron	3% 0.42 mg
Magnesium	1% 2 mg
Phosphorus	1% 4 mg
Potassium	0% 0 mg
Sodium	0% 2 mg
Zinc	2% 0.22 mg
Other constituents	Quantity
Water	24 g
Full report from USDA National Nutrient Database
Units μg = micrograms • mg = milligrams IU = International units
†Percentages are roughly approximated using US recommendations for adults. Source: USDA Nutrient Database

Nutrition

HFCS is 76% carbohydrates and 24% water, containing no fat, protein, or micronutrients in significant amounts (table). In a 100-gram serving, it supplies 281 calories, while in one tablespoon of 19 grams, it supplies 53 calories (table link).

Obesity and metabolic syndrome

There is no scientific evidence that HFCS itself causes obesity or metabolic syndrome, but rather overconsumption and excessive caloric intake of any sweetened food or beverage may contribute to these diseases. Epidemiological research has shown that the increase in metabolic disorders, such as obesity and non-alcoholic fatty liver disease, is linked to increased consumption of sugars and calories in general. A 2012 review found that fructose did not appear to cause weight gain when it replaced other carbohydrates in diets with similar calories. A 2014 systematic review found little evidence for an association between HFCS consumption and liver diseases, enzyme levels or fat content. A 2018 review by the university of Colorado found that diets high in fructose can cause the Nonalcoholic Fatty Liver Disease, due to the conversion of fructose by fructokinase C, resulting in ATP consumption, nucleotide turnover and uric acid generation that mediate fat accumulation. The American Heart Association recommended that people limit added sugar (such as maltose, sucrose, high fructose corn syrup, molasses or cane sugar) in their diets.

Safety and manufacturing concerns

Since 2014, the United States Food and Drug Administration (FDA) has determined that HFCS is safe as an ingredient for food and beverage manufacturing. and there is no evidence that retail HFCS products differ in safety from those containing alternative nutritive sweeteners. The 2010 Dietary Guidelines for Americans recommended that added sugars should be limited in the diet.

One consumer concern about HFCS is that processing of corn is more complex than used for “simpler” or “more natural” sugars, such as fruit juice concentrates or agave nectar, but all sweetener products derived from raw materials involve similar processing steps of pulping, hydrolysis, enzyme treatment, and filtration, among other common steps of sweetener manufacturing from natural sources. In the contemporary process to make HFCS, an "acid-enzyme" step is used in which the corn starch solution is acidified to digest the existing carbohydrates, then enzymes are added to further metabolize the corn starch and convert the resulting sugars to their constituents of fructose and glucose. Analyses published in 2014 showed that HFCS content of fructose was consistent across samples from 80 randomly selected carbonated beverages sweetened with HFCS.

One prior concern in manufacturing was whether HFCS contains reactive carbonyl compounds or advanced glycation end-products evolved during processing. This concern was dismissed, however, with evidence that HFCS poses no dietary risk from these compounds.

Through the early 21st Century, some factories manufacturing HFCS had used a chlor-alkali corn processing method which, in cases of applying mercury cell technology for digesting corn raw material, left trace residues of mercury in some batches of HFCS. In a 2009 release, The Corn Refiners Association stated that all factories in the American industry for manufacturing HFCS had used mercury-free processing over several previous years, making the prior report outdated. As of 2018, the USDA, FDA and US Centers for Disease Control list HFCS as a safe food ingredient, and do not mention mercury as a safety concern in HFCS products.

Fructose concentration and consistency

The USFDA has recognized that studies have found differences between how humans metabolize fructose compared to other simple sugars. The agency does not consider HFCS-42 nor HFCS-55 to be better or worse for health due to it providing a relatively equivalent amount of dietary fructose as other approved sweeteners. Expressed in a 2013 review; “dietary fructose consumption, which cannot be measured by conventional dietary methods because the fructose content of HFCS is not disclosed, may be much higher than...common assumptions.”

Other

Taste difference

Most countries, including Mexico, use sucrose, or table sugar, in soft drinks. In the U.S., soft drinks, such as Coca-Cola, are typically made with HFCS 55. HFCS has a sweeter taste than glucose. Some Americans seek out drinks such as Mexican Coca-Cola in ethnic groceries because they prefer the taste over that of HFCS-sweetened Coca-Cola. Kosher Coca-Cola, sold in the U.S. around the Jewish holiday of Passover, also uses sucrose rather than HFCS and is highly sought after by people who prefer the original taste. While these are simply opinions, a 2011 study further backed up the idea that people enjoy sucrose (table sugar) more than HFCS. The study, conducted by Michigan State University, included a 99-member panel that evaluated yogurt sweetened with sucrose (table sugar), HFCS, and different varieties of honey for likeness. The results showed that, overall, the panel enjoyed the yogurt with sucrose (table sugar) added more than those that contained HFCS or honey.

Beekeeping

In apiculture in the United States, HFCS is a honey substitute for some managed honey bee colonies during times when nectar is in low supply. However, when HFCS is heated to about 45 °C (113 °F), hydroxymethylfurfural, which is toxic to bees, can form from the breakdown of fructose. Although some researchers cite honey substitution with HFCS as one factor among many for colony collapse disorder, there is no evidence that HFCS is the only cause. Compared to hive honey, both HFCS and sucrose caused signs of malnutrition in bees fed with them, apparent in the expression of genes involved in protein metabolism and other processes affecting honey bee health.

Public relations

There are various public relations concerns with HFCS, including how HFCS products are advertised and labeled as "natural". As a consequence, several companies reverted to manufacturing with sucrose (table sugar) from products that had previously been made with HFCS. In 2010, the Corn Refiners Association (CRA) applied to allow HFCS to be renamed "corn sugar", but that petition was rejected by the United States Food and Drug Administration in 2012.

In August 2016 in a move to please consumers with health concerns, McDonald's announced they would be replacing all HFCS in their buns with sucrose (table sugar) and would cut out preservatives and other artificial additives from their menu items. Marion Gross, senior vice president of McDonald's stated, "We know that they [consumers] don't feel good about high-fructose corn syrup so we're giving them what they're looking for instead." Over the early 21st century, other companies such as Yoplait, Gatorade, and Hershey's also phased out HFCS, replacing it with conventional sugar because consumers perceived sugar to be healthier. Companies such as PepsiCo and Heinz have also released products that use sugar in lieu of HFCS, although they still sell HFCS-sweetened products.

History

Commercial production of corn syrup began in 1964. In the late 1950s, scientists at Clinton Corn Processing Company of Clinton, Iowa, tried to turn glucose from corn starch into fructose, but the process was not scalable. In 1965–1970 Yoshiyuki Takasaki, at the Japanese National Institute of Advanced Industrial Science and Technology (AIST) developed a heat-stable xylose isomerase enzyme from yeast. In 1967, the Clinton Corn Processing Company obtained an exclusive license to manufacture glucose isomerase derived from Streptomyces bacteria and began shipping an early version of HFCS in February 1967. In 1983, the FDA approved HFCS as Generally Recognized as Safe (GRAS), and that decision was reaffirmed in 1996.

Prior to the development of the worldwide sugar industry, dietary fructose was limited to only a few items. Milk, meats, and most vegetables, the staples of many early diets, have no fructose, and only 5–10% fructose by weight is found in fruits such as grapes, apples, and blueberries. Most traditional dried fruits, however, contain about 50% fructose. From 1970 to 2000, there was a 25% increase in "added sugars" in the U.S. When recognized as a cheaper, more versatile sweetener, HFCS replaced sucrose as the main sweetener of soft drinks in the United States. 

Since 1789, the U.S. sugar industry has had trade protection against tariffs imposed by foreign-produced sugar, while subsidies to corn growers cheapen the primary ingredient in HFCS, corn. Industrial users looking for cheaper replacements rapidly adopted HFCS in the 1970s.

Mama Juana

From Wikipedia, the free encyclopedia

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

Mamajuana

Mama Juana (or Mamajuana) is a drink from the Dominican Republic that is concocted by allowing rum, red wine, and honey to soak in a bottle with tree bark and herbs. The taste is similar to port wine and the color is a deep red.

The specific herbs that make up Mamajuana were originally prepared as an herbal tea by the native Taíno; post-Columbus, alcohol was added to the recipe.

Etymology

The term Mama Juana has the same French origins as the English word demijohn, which refers to a large squat bottle with a short narrow neck, usually covered in wicker. It is thought to be derived from the French Dame Jeanne (Lady Jane), a term still used to describe this type of bottle. In the Spanish-speaking countries, Dame Jeanne was transformed into "damajuana", or Dama Juana and later, in the Dominican Republic, into Mama Juana (mother Jane). There are many different variations of recipes to make Mamajuana, since the name refers to the container or bottle originally used to prepare and store the maceration, rather than to the finished product itself.

History

Rodriguez (left) and Tatico Henriquez (right) holding a glass jug of home-made Mama Juana

Mama Juana is considered one of the first distilled spirits in the Americas, even before rum, considering that early Spanish explorers mixed European alcohol with the Taínos' herbal tea; this combination created the first Mama Juana.

During the dictatorship of Rafael Trujillo, the sale of Mama Juana was prohibited, except by those with a medical license.

Mama Juana was popularized as a local herbal medicine and aphrodisiac in the 1950s by Jesus Rodriguez, a native of San Juan de la Maguana. Rodriguez would commute with others in trucks to Barahona, Azua, Pedernales, and many other provinces in the Dominican Republic to collect the stems needed to create the medicinal drink. He would reportedly use carne ce carey (leatherback turtle meat), which was the active ingredient that made the aphrodisiac. Rodriguez eventually would be known under the moniker "Mama Juana" by many of the locals, as well as Tatico Henriquez and other merengue típico artists, such as Trio Reynoso and El Cieguito De Nagua, who were close friends of Rodriguez.

Another notable Mama Juana drinker was Porfirio Rubirosa, the famous Dominican playboy, polo player, race-car driver, and secret agent. Rubirosa was famous for his sexual prowess, and was known to be an avid mamajuana drinker, as mentioned in his biography, The Last Playboy.

Dominican playboy, Porfirio Rubirosa.

Preparation

Mama Juana is a mixture of bark and herbs left to soak in rum (most often dark rum but the use of white rum is not uncommon), red wine and honey. The solid ingredients (local leaves, barks, sticks and roots) vary from region to region but usually include some of the following:

• Anamú (Petiveria alliacea)
• Anis estrellado (star anise, Illicium verum)
• Bohuco pega-palo (Cissus verticillata)
• Albahaca (basil, Ocimum basilicum)
• Canelilla (Cinnamodendron ekmanii)
• Bojuco caro (princess vine)
• Marabeli (Securidaca virgata)
• Clavo dulce (whole clove)
• Maguey (Agave spp.) leaves
• Timacle (Chiococca alba)

In addition to the above standard recipe, it is common for individuals to add other ingredients such as cinnamon, raisins, strawberry, molasses, and lemon or lime juice. Some recipes are said to include grated tortoiseshell, or sea turtle penis shaft for aphrodisiac effect. The concoction is usually kept at room temperature and served in a shot glass.

Consuming

Mamajuana is available in three varieties:

• Prepackaged dry ingredients, which the customer cures and macerates
• Ready to drink, including the ingredients in the bottle
• Ready to drink, filtered and bottled

Example of Candela, a premium Mamajuana.

The most common way of consuming mamajuana in the Dominican Republic is neat (straight up) or as a room-temperature shot.

With the popularization of ready to drink brands, there has been a growing interest for mamajuana amongst mixologists. Many bars, restaurants and other on-premise establishments now offer mamajuana recipes in their beverage programs.

In recent years, the consumption of mamajuana has seen a sharp rise, with commercial brands becoming available in the Dominican Republic and internationally. Premium brands, such as Candela and Anteroz and economy brands such as Karibú and Kalembú, can be purchased in duty-free shops, resorts and liquor stores.

Besides the Dominican Republic, there has also been an increase in mamajuana consumption in Miami, New York, New Jersey, Pennsylvania, Spain, Chile, Cuba and Perú. With the introduction of commercial brands Mamajuana is becoming known worldwide.