Sodium erythorbate

Sodium erythorbate[1][2][3]
Sodium erythorbate
Sodium erythorbate
Names
IUPAC name
Sodium 1,4-anhydro-1-oxo-D-erythro-hex-2-enitol-3-O-ate
Systematic IUPAC name
Sodium (2R)-2-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate
Other names
D-isoascorbate; erythorbic acid, sodium salt; E316; araboascorbic acid, monosodium salt, D- (6CI); D-erythro-hex-2-enonic acid, γ-lactone, monosodium salt (8CI,9CI); Erbit N; Eribate N; isoascorbate C sodium; Isona; sodium isoascorbate; sodium D-isoascorbate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.026.340 Edit this at Wikidata
EC Number
  • 228-973-9
E number E316 (antioxidants, ...)
UNII
  • InChI=1S/C6H8O6.Na/c7-1-2(8)5-3(9)4(10)6(11)12-5;/h2,5,7-10H,1H2;/q;+1/p-1/t2-,5-;/m1./s1 ☒N
    Key: PPASLZSBLFJQEF-RKJRWTFHSA-M ☒N
  • 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
  • [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-]
Properties
C6H7NaO6
Molar mass 198.11 g/mol
Appearance White crystalline solid
Density 1.2
Melting point 168 to 170 °C (334 to 338 °F; 441 to 443 K)
16 g/100 mL
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

Uses

When used in processed meat such as hot dogs, bologna,[4] and beef sticks, it increases the rate at which nitrite reduces to nitric oxide, thus facilitating a faster cure and retaining the pink coloring. As an antioxidant structurally related to vitamin C, it helps improve flavor stability and prevents the formation of carcinogenic nitrosamines. When used as a food additive, its E number is E316.[5]

The use of erythorbic acid and sodium erythorbate as a food preservative has increased greatly since the U.S. Food and Drug Administration banned the use of sulfites as preservatives in foods intended to be eaten fresh (such as ingredients for fresh salads) and as food processors have responded to the fact that some people are allergic to sulfites.[6]

It is occasionally used in beverages, baked goods, and potato salad.[4]

Alternative applications include the development of additives that could be utilized as antioxidants in general. For instance, this substance has been implemented in the development of corrosion inhibitors for metals[7] and it has been implemented in active packaging.[8] Furthermore, sodium erythorbate's antioxidative properties have been shown to reduce the production thiobarbituric acid reactive substances (TBARS) in frozen meats, effectively increasing their shelf-life.[9]

Production

Main article: Erythorbic acid § Production

Sodium erythorbate is produced from sugars derived from different sources, such as beets, sugarcane, and corn. These sugars are converted to ordinary D-glucose.[10][11][12] The glucose is converted to a 2-keto sugar acid intermediate, most commonly 2-keto-D-gluconic acid, by Pseudomonas fluorescens bacteria.[13]

An urban myth claims that sodium erythorbate is made from ground earthworms; however, there is no truth to the myth.[14] It is thought that the origin of the legend comes from the similarity of the chemical name to the words earthworm and bait.[14]

Chemistry

Sodium erythorbate is soluble in water. The pH of the aqueous solution of the sodium salt is between 5 and 6. A 10% solution, made from commercial grade sodium erythorbate, may have a pH of 7.2 to 7.9.[15] In its dry, crystalline state it is nonreactive. But, when in solution with water it readily reacts with atmospheric oxygen and other oxidizing agents, which makes it a valuable antioxidant.[4]z

References

  1. ^ Merck Index, 11th Edition, 5009.
  2. ^ "CAS Registry Number 6381-77-7". SciFinder. Retrieved 14 November 2016.
  3. ^ "Sodium erythorbate | C6H7NaO6 - PubChem". PubChem. National Center for Biotechnology Information. Retrieved 13 November 2022.
  4. ^ a b c Igoe, R. S. (2011). Dictionary of Food Ingredients. Boston, MA: Springer US. pp. 129. ISBN 9781441997128.
  5. ^ Current EU approved additives and their E Numbers, Food Standards Agency
  6. ^ Hui, Y. H. (2006). Handbook of Food Science, Technology and Engineering. CRC Press. p. 83-32. ISBN 0-8493-9848-7.
  7. ^ Christensen RJ, Steimel LH, Oxygen scavenger for boiler water and method of use. US patent 4,891,141. 1990
  8. ^ R. Joven, A. Garcia, A. Arias, J. Medina. Development of an active thermoplastic film with oxygen scavengers made of activated carbon and sodium erythorbate. In: Packaging Technology and Science, Vol 28, No. 2; 01/2015.
  9. ^ Silveira Alexandre, Ana Cláudia; Corrêa Albergaria, Francielly; dos Santos Ferraz e Silva, Lara Maria; Carneiro Fernandes, Luíza Aparecida; de Sousa Gomes, Maria Emília; Pimenta, Carlos José (15 January 2022). "Effect of natural and synthetic antioxidants on oxidation and storage stability of mechanically separated tilapia meat". LWT - Food Science and Technology. 154: 112679. doi:10.1016/j.lwt.2021.112679.
  10. ^ "Sodium Erythorbate". PMP Fermentation Products, Inc. Archived from the original on January 11, 2010. Retrieved 2008-10-27.
  11. ^ "Sodium Erythorbate (Archive Copy - Original not available?)". PMP Fermentation Products, Inc. Archived from the original on January 11, 2010. Retrieved 2011-10-23.
  12. ^ "Sodium erythorbate".
  13. ^ Andersen, FA (1999). "Final Report on the Safety Assessment of Ascorbyl Palmitate, Ascorbyl Dipalmitate, Ascorbyl Stearate, Erythorbic Acid, and sodium Erythorbate". International Journal of Toxicology. 18(3_suppl) (3_suppl): 1–26. doi:10.1177/109158189901800303. S2CID 85834903. Retrieved 13 November 2022 – via SAGE Publishing.
  14. ^ a b Sodium Erythorbate - is it an earthworm?, Oregon Department of Agriculture
  15. ^ The Merck Index (14th ed.). Merck Research Laboratories. 2006. pp. Page 890, section 5126.