Erythorbic acid

Erythorbic acid
Names
IUPAC name
(5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
Other names
D-Araboascorbic acid, Erythorbate, Isoascorbic acid, E315
Identifiers
89-65-6 YesY
ChEBI CHEBI:51438 YesY
ChemSpider 16736142 YesY
Jmol interactive 3D Image
PubChem 6981
UNII 311332OII1 YesY
Properties
C6H8O6
Molar mass 176.12 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
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Erythorbic acid (isoascorbic acid, D-araboascorbic acid) is a stereoisomer 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]

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.[5]

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.[6]

It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.[7][8]

See also

References

  1. ↑ Erythorbic acid and its sodium salt Dr R. Walker, Professor of Food Science, Department of Biochemistry, University of Surrey, England.
  2. ↑ https://pubchem.ncbi.nlm.nih.gov/compound/Erythorbic_acid#section=Industry-Uses
  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): pp. 336–46. 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. PMID 14684404.
  6. ↑ Hui YH (2006). Handbook of Food Science, Technology and Engineering. CRC Press. pp. 83–32. ISBN 0-8493-9848-7.
  7. ↑ See:
    • Kurt Maurer and Bruno Schiedt (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.
    • Kurt Maurer and Bruno Schiedt (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.
  8. ↑ See also:
    • Heinz Ohle, Heinz Erlbach and Herbert Carls (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.
    • 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.
    • T. Reichstein, A. Grüssner, and R. Oppenauer (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.
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