Home  

Random  

Nearby  



Log in  



Settings  



Donate  



About Wikipedia  

Disclaimers  



Wikipedia





Erythorbic acid





Article  

Talk  



Language  

Watch  

Edit  





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

Erythorbic acid
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.

Identifiers

CAS Number

3D model (JSmol)

ChEBI
ChemSpider
ECHA InfoCard 100.001.753 Edit this at Wikidata
E number E315 (antioxidants, ...)

PubChem CID

UNII

CompTox Dashboard (EPA)

  • 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 checkY

    Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N checkY

  • 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

Chemical formula

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 four-colored diamondHealth 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).

checkY verify (what is checkY☒N ?)

Infobox references

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]

References

edit
  1. ^ Erythorbic acid and its sodium salt Dr R. Walker, Professor of Food Science, Department of Biochemistry, University of Surrey, England.
  • ^ "Erythorbic acid".
  • ^ Current EU approved additives and their E Numbers, Food Standards Agency
  • ^ 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.
  • ^ 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.
  • ^ Hui YH (2006). Handbook of Food Science, Technology and Engineering. CRC Press. pp. 83–32. ISBN 0-8493-9848-7.
  • ^ 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.
  • ^ 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.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Erythorbic_acid&oldid=1153550686"
     



    Last edited on 7 May 2023, at 01:59  





    Languages

     


    تۆرکجه
    Català
    Deutsch
    Español
    فارسی
    Français
    Italiano
    Lietuvių
    Magyar
    Nederlands

    Português
    Română
    Slovenčina
    Српски / srpski
    Srpskohrvatski / српскохрватски
    Suomi
    Svenska
    Tiếng Vit

     

    Wikipedia


    This page was last edited on 7 May 2023, at 01:59 (UTC).

    Content is available under CC BY-SA 4.0 unless otherwise noted.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Terms of Use

    Desktop