Erythorbic acid

Last updated
Erythorbic acid
D-Erythorbic acid.svg
Erythorbic-acid-3D-balls.png
Names
IUPAC name
D-erythro-Hex-2-enono-1,4-lactone
Systematic IUPAC name
(5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
Other names
D-Araboascorbic acid, Erythorbate, Isoascorbic acid, D-isoascorbic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.753 OOjs UI icon edit-ltr-progressive.svg
E number E315 (antioxidants, ...)
PubChem CID
UNII
  • InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1 Yes check.svgY
    Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N Yes check.svgY
  • InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1
    Key: CIWBSHSKHKDKBQ-DUZGATOHBV
  • OC=1[C@H](OC(=O)C=1O)[C@H](O)CO
Properties
C6H8O6
Molar mass 176.124 g·mol−1
Density 0.704 g/cm3
Melting point 164 to 172 °C (327 to 342 °F; 437 to 445 K) (decomposes)
Acidity (pKa)2.1
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Related compounds
Other cations
Calcium erythorbate, sodium erythorbate, potassium erythorbate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Erythorbic acid (isoascorbic acid, D-araboascorbic acid) is a stereoisomer (C5 epimer) of ascorbic acid (vitamin C). [1] It is synthesized by a reaction between methyl 2-keto-D-gluconate and sodium methoxide. It can also be synthesized from sucrose or by strains of Penicillium that have been selected for this feature. [2] It is denoted by E number E315, and is widely used as an antioxidant in processed foods. [3]

Contents

Health effects

Clinical trials have been conducted to investigate aspects of the nutritional value of erythorbic acid. One such trial investigated the effects of erythorbic acid on vitamin C metabolism in young women; no effect on vitamin C uptake or clearance from the body was found. [4]

A later study found that erythorbic acid is a potent enhancer of nonheme-iron absorption, just like ascorbate. This is thought to be due to it exerting the same iron-reducing and iron-chelating activity as ascorbic acid. Neither of these reactions is mediated by an enzyme, which would confer some chiral selectivity. [5] It is twice as effective as ascorbic acid in enhancing non-heme iron absorption. Americans are estimated to ingest 200 mg of erythorbic acid per day, making it a very important factor in understanding iron absorption. [6]

Uses

Since the U.S. Food and Drug Administration banned the use of sulfites as a preservative in foods intended to be eaten fresh (such as salad bar ingredients), the use of erythorbic acid as a food preservative has increased.

It is also used as a preservative in cured meats and frozen vegetables. [7] Much like ascorbic acid, it increases nitrosylation of the central iron atom of muscle myoglobin, resulting in the formation of reddish-brown nitrosomyoglobin and the characteristic pink color of nitrosohemochrome or nitrosyl-heme upon cooking. [8] Again like ascorbic acid, it reduces the formation of nitrosamines. [9]

History

It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt. [10] [11]

Production

Erythorbic acid is very easily produced by fermentation, being obtainable in just one step compared to ascorbic acid's two. A number of Penicillium naturally produce this chemical from glucose. This is the original process developed in the 1960s, but it has low volumetric efficiency and glucose yield compared to the modern method. [8]

Today the industrial process is quite similar to the Reichstein process used for ascorbic acid, only chirally flipped. Microbial fermentation first produces a 2-keto-sugar acid, e.g. by Pseudomonas fluorescens AR4 converting glucose to 2-keto-D-gluconate. Then chemical rearrangement produces the product. [8]

Economics

Like ascorbic acid, the production of erythorbic acid is concentrated in China. Its price is less volatile than that of ascorbic acid, making it an attractive alternative in non-nutritive uses in times of high ascorbic acid prices. [8]

The structually similar C5 sugar acid, D-erythroascorbic acid, is made by baker's yeast and other fungi, acting as an antioxidant in their own cells. It is made by and has some antioxidant activity in Manduca sexta . [12] It has no industrial use, however. [8]

Related Research Articles

<span class="mw-page-title-main">Chemistry of ascorbic acid</span> Chemical compound

Ascorbic acid is an organic compound with formula C
6
H
8
O
6
, originally called hexuronic acid. It is a white solid, but impure samples can appear yellowish. It dissolves freely in water to give mildly acidic solutions. It is a mild reducing agent.

Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants are frequently added to industrial products, such as polymers, fuels, and lubricants, to extend their usable lifetimes. Foods are also treated with antioxidants to forestall spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol, or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress.

A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.

<span class="mw-page-title-main">Vitamin C</span> Essential nutrient found in citrus fruits and other foods

Vitamin C is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription dietary supplement. As a therapy, it is used to prevent and treat scurvy, a disease caused by vitamin C deficiency.

A nutrient is a substance used by an organism to survive, grow and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi and protists. Nutrients can be incorporated into cells for metabolic purposes or excreted by cells to create non-cellular structures such as hair, scales, feathers, or exoskeletons. Some nutrients can be metabolically converted into smaller molecules in the process of releasing energy such as for carbohydrates, lipids, proteins and fermentation products leading to end-products of water and carbon dioxide. All organisms require water. Essential nutrients for animals are the energy sources, some of the amino acids that are combined to create proteins, a subset of fatty acids, vitamins and certain minerals. Plants require more diverse minerals absorbed through roots, plus carbon dioxide and oxygen absorbed through leaves. Fungi live on dead or living organic matter and meet nutrient needs from their host.

Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.

The nitrite ion has the chemical formula NO
2
. Nitrite is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also refers to organic compounds having the –ONO group, which are esters of nitrous acid.

<span class="mw-page-title-main">Nitrosamine</span> Organic compounds of the form >N–N=O

Nitrosamines are organic compounds produced by industrial processes.

The Japp–Klingemann reaction is a chemical reaction used to synthesize hydrazones from β-keto-acids and aryl diazonium salts. The reaction is named after the chemists Francis Robert Japp and Felix Klingemann.

<small>L</small>-gulonolactone oxidase Enzyme involved in the synthesis of vitamin C

L-Gulonolactone oxidase is an enzyme that produces vitamin C. It is expressed in most mammals, but is non-functional in Haplorrhini, in some bats, and in guinea pigs. It catalyzes the reaction of L-gulono-1,4-lactone with oxygen to form L-xylo-hex-3-gulonolactone (2-keto-gulono-γ-lactone) and hydrogen peroxide. It uses FAD as a cofactor. The L-xylo-hex-3-gulonolactone then converts to ascorbic acid spontaneously, without enzymatic action. The structure of L-gulonolactone oxidase in rats helps identify characteristics of this enzyme.

<span class="mw-page-title-main">Sodium erythorbate</span> Chemical compound

Sodium erythorbate (C6H7NaO6) is a food additive used predominantly in meats, poultry, and soft drinks. Chemically, it is the sodium salt of erythorbic acid.

The Reed reaction is a chemical reaction that utilizes light to oxidize hydrocarbons to alkylsulfonyl chlorides. This reaction is employed in modifying polyethylene to give chlorosulfonated polyethylene (CSPE), which is noted for its toughness.

The Rosenmund reduction is a hydrogenation process in which an acyl chloride is selectively reduced to an aldehyde. The reaction was named after Karl Wilhelm Rosenmund, who first reported it in 1918.

Chlorobutanol (trichloro-2-methyl-2-propanol) is an organic compound with the formula CCl3C(OH)(CH3)2. The compound is an example of a chlorohydrin. The compound is a preservative, sedative, hypnotic and weak local anesthetic similar in nature to chloral hydrate. It has antibacterial and antifungal properties. Chlorobutanol is typically used at a concentration of 0.5% where it lends long term stability to multi-ingredient formulations. However, it retains antimicrobial activity at 0.05% in water. Chlorobutanol has been used in anesthesia and euthanasia of invertebrates and fishes. It is a white, volatile solid with a camphor-like odor.

The Schotten–Baumann reaction is a method to synthesize amides from amines and acid chlorides:

The Reichstein process in chemistry is a combined chemical and microbial method for the production of ascorbic acid from D-glucose that takes place in several steps. This process was devised by Nobel Prize winner Tadeusz Reichstein and his colleagues in 1933 while working in the laboratory of the ETH in Zürich.

The Fiesselmann thiophene synthesis is a name reaction in organic chemistry that allows for the generation of 3-hydroxy-2-thiophenecarboxylic acid derivatives from α,β-acetylenic esters with thioglycolic acid and its derivatives under the presence of a base. The reaction was developed by Hans Fiesselmann in the 1950s.

In biochemistry, nitrosamines are a class of compounds that can form during food digestion. The presence of their precursors, nitrites, in cured meats, is controversial, because of a small connection to cancer risk.

References

  1. Erythorbic acid and its sodium salt Dr R. Walker, Professor of Food Science, Department of Biochemistry, University of Surrey, England.
  2. "Erythorbic acid".
  3. Current EU approved additives and their E Numbers, Food Standards Agency
  4. Sauberlich, HE; Tamura T; Craig CB; Freeberg LE; Liu T (September 1996). "Effects of erythorbic acid on vitamin C metabolism in young women". American Journal of Clinical Nutrition. 64 (3): 336–46. doi: 10.1093/ajcn/64.3.336 . PMID   8780343.
  5. Fidler, MC; Davidsson L; Zeder C; Hurrell RF (January 2004). "Erythorbic acid is a potent enhancer of nonheme-iron absorption". American Journal of Clinical Nutrition. 79 (1): 99–102. doi: 10.1093/ajcn/79.1.99 . PMID   14684404.
  6. Hurrell, Richard; Egli, Ines (May 2010). "Iron bioavailability and dietary reference values". The American Journal of Clinical Nutrition. 91 (5): 1461S –1467S. doi:10.3945/ajcn.2010.28674F.
  7. Hui YH (2006). Handbook of Food Science, Technology and Engineering. CRC Press. pp. 83–32. ISBN   0-8493-9848-7.
  8. 1 2 3 4 5 Pappenberger, Günter; Hohmann, Hans-Peter (2013). "Industrial Production of l-Ascorbic Acid (Vitamin C) and d-Isoascorbic Acid". Biotechnology of Food and Feed Additives. 143: 143–188. doi:10.1007/10_2013_243.
  9. Herrmann, S.S.; Granby, K.; Duedahl-Olesen, L. (May 2015). "Formation and mitigation of N-nitrosamines in nitrite preserved cooked sausages". Food Chemistry. 174: 516–526. doi: 10.1016/j.foodchem.2014.11.101 .
  10. See:
    • Maurer, Kurt; Schiedt, Bruno (August 2, 1933). ""Die Darstellung einer Säure C6H8O6 aus Glucose, die in ihrer Reduktionskraft der Ascorbinsäure gleicht (Vorläuf. Mitteil.)" (The preparation of an acid C6H8O6 from glucose, which equals ascorbic acid in its reducing power (preliminary report))". Berichte der Deutschen Chemischen Gesellschaft. 66 (8): 1054–1057. doi:10.1002/cber.19330660807.
    • Maurer, Kurt; Schiedt, Bruno (July 4, 1934). ""Zur Darstellung des Iso-Vitamins C (d-Arabo-ascorbinsäure) (II. Mitteil.)" (On the preparation of iso-vitamin C (d-arabo-ascorbic acid) (2nd report))". Berichte der Deutschen Chemischen Gesellschaft. 67 (7): 1239–1241. doi:10.1002/cber.19340670724.
  11. See also:
    • Ohle, Heinz; Erlbach, Heinz; Carls, Herbert (February 7, 1934). ""d-Gluco-saccharosonsäure, ein Isomeres der Ascorbinsäure, I. Mitteil.: Darstellung und Eigenschaften" (d-Gluco-saccharosonic acid, an isomer of ascorbic acid, 1st report: preparation and properties)". Berichte der Deutschen Chemischen Gesellschaft. 67 (2): 324–332. doi:10.1002/cber.19340670235.
    • Baird, D. K.; Haworth, W. N.; Herbert, R. W.; Hirst, E. L.; Smith, F.; Stacey, M. (1934). "Ascorbic acid and synthetic analogues". Journal of the Chemical Society: 63–67. doi:10.1039/JR9340000062.
    • Reichstein, T.; Grüssner, A.; Oppenauer, R. (1934). ""Synthese der Ascorbinsäure und verwandter Verbindungen nach der Oson-Blausäure-Methode"(Synthesis of ascorbic acid and related compounds via the ozone-hydrogen cyanide method)". Helvetica Chimica Acta. 17: 510–520. doi:10.1002/hlca.19340170157.
  12. Shao, Yi Yuan.; Seib, Paul A.; Kramer, Karl J.; Van Galen, Dean A. (1 September 1993). "Synthesis and properties of D-erythroascorbic acid and its vitamin C activity in the tobacco hornworm (Manduca sexta)". Journal of Agricultural and Food Chemistry. 41 (9): 1391–1396. doi:10.1021/jf00033a009.