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Sodium erythorbate

Sodium erythorbate (C6H7NaO6) is a food additive used predominantly in meats, poultry, and soft drinks. Chemically, it is the sodium salt of erythorbic acid. When used in processed meat such as hot dogs 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.[4] 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.[5] It can also be found in bologna, and is occasionally used in beverages, baked goods, and potato salad.[6] Sodium erythorbate is produced from sugars derived from different sources, such as beets, sugarcane, and corn.[7][8][9] Sodium erythorbate is usually produced via a fermentation process from D-glucose by Pseudomonas fluorescens bacteria.[10] Most syntheses proceed through the 2-keto-D-gluconic acid intermediate.[10] An urban myth claims that sodium erythorbate is made from ground earthworms; however, there is no truth to the myth.[11] It is thought that the origin of the legend comes from the similarity of the chemical name to the words earthworm and bait.[11]

Sodium erythorbate[1][2][3]
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
  • 6381-77-7 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:51438 Y
ChemSpider
  • 16736142 Y
ECHA InfoCard 100.026.340
EC Number
  • 228-973-9
E number E316 (antioxidants, ...)
  • 23683938
UNII
  • BZ468R6XRD Y
  • DTXSID5020570
  • 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)
Health 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 YN ?)

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[12] and it has been implemented in active packaging.[13] 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.[14]

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.[6]

References edit

  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. ^ Current EU approved additives and their E Numbers, Food Standards Agency
  5. ^ Hui, Y. H. (2006). Handbook of Food Science, Technology and Engineering. CRC Press. p. 83-32. ISBN 0-8493-9848-7.
  6. ^ a b Igoe, R. S. (2011). Dictionary of Food Ingredients. Boston, MA: Springer US. pp. 129. ISBN 9781441997128.
  7. ^ . PMP Fermentation Products, Inc. Archived from the original on January 11, 2010. Retrieved 2008-10-27.
  8. ^ . PMP Fermentation Products, Inc. Archived from the original on January 11, 2010. Retrieved 2011-10-23.{{cite web}}: CS1 maint: unfit URL (link)
  9. ^ "Sodium erythorbate".
  10. ^ a b 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.
  11. ^ a b Sodium Erythorbate - is it an earthworm?, Oregon Department of Agriculture
  12. ^ Christensen RJ, Steimel LH, Oxygen scavenger for boiler water and method of use. US patent 4,891,141. 1990
  13. ^ 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.
  14. ^ 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.
  15. ^ The Merck Index (14th ed.). Merck Research Laboratories. 2006. pp. Page 890, section 5126.

sodium, erythorbate, c6h7nao6, food, additive, used, predominantly, meats, poultry, soft, drinks, chemically, sodium, salt, erythorbic, acid, when, used, processed, meat, such, dogs, beef, sticks, increases, rate, which, nitrite, reduces, nitric, oxide, thus, . Sodium erythorbate C6H7NaO6 is a food additive used predominantly in meats poultry and soft drinks Chemically it is the sodium salt of erythorbic acid When used in processed meat such as hot dogs 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 4 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 5 It can also be found in bologna and is occasionally used in beverages baked goods and potato salad 6 Sodium erythorbate is produced from sugars derived from different sources such as beets sugarcane and corn 7 8 9 Sodium erythorbate is usually produced via a fermentation process from D glucose by Pseudomonas fluorescens bacteria 10 Most syntheses proceed through the 2 keto D gluconic acid intermediate 10 An urban myth claims that sodium erythorbate is made from ground earthworms however there is no truth to the myth 11 It is thought that the origin of the legend comes from the similarity of the chemical name to the words earthworm and bait 11 Sodium erythorbate 1 2 3 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 g lactone monosodium salt 8CI 9CI Erbit N Eribate N isoascorbate C sodium Isona sodium isoascorbate sodium D isoascorbate Identifiers CAS Number 6381 77 7 Y 3D model JSmol Interactive image ChEBI CHEBI 51438 Y ChemSpider 16736142 Y ECHA InfoCard 100 026 340 EC Number 228 973 9 E number E316 antioxidants PubChem CID 23683938 UNII BZ468R6XRD Y CompTox Dashboard EPA DTXSID5020570 InChI 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 NKey PPASLZSBLFJQEF RKJRWTFHSA M NInChI 1 C6H8O6 c7 1 2 8 5 3 9 4 10 6 11 12 5 h2 5 7 10H 1H2 t2 5 m1 s1Key CIWBSHSKHKDKBQ DUZGATOHBV SMILES Na OC C H O C H 1OC O C O C1 O Properties Chemical formula 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 Solubility in water 16 g 100 mL Hazards NFPA 704 fire diamond 110 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 12 and it has been implemented in active packaging 13 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 14 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 6 References edit Merck Index 11th Edition 5009 CAS Registry Number 6381 77 7 SciFinder Retrieved 14 November 2016 Sodium erythorbate C6H7NaO6 PubChem PubChem National Center for Biotechnology Information Retrieved 13 November 2022 Current EU approved additives and their E Numbers Food Standards Agency Hui Y H 2006 Handbook of Food Science Technology and Engineering CRC Press p 83 32 ISBN 0 8493 9848 7 a b Igoe R S 2011 Dictionary of Food Ingredients Boston MA Springer US pp 129 ISBN 9781441997128 Sodium Erythorbate PMP Fermentation Products Inc Archived from the original on January 11 2010 Retrieved 2008 10 27 Sodium Erythorbate Archive Copy Original not available PMP Fermentation Products Inc Archived from the original on January 11 2010 Retrieved 2011 10 23 a href Template Cite web html title Template Cite web cite web a CS1 maint unfit URL link Sodium erythorbate a b 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 a b Sodium Erythorbate is it an earthworm Oregon Department of Agriculture Christensen RJ Steimel LH Oxygen scavenger for boiler water and method of use US patent 4 891 141 1990 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 Silveira Alexandre Ana Claudia Correa Albergaria Francielly dos Santos Ferraz e Silva Lara Maria Carneiro Fernandes Luiza Aparecida de Sousa Gomes Maria Emilia Pimenta Carlos Jose 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 The Merck Index 14th ed Merck Research Laboratories 2006 pp Page 890 section 5126 Retrieved from https en wikipedia org w index php title Sodium erythorbate amp oldid 1198585142, wikipedia, wiki, book, books, library,

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