Sodium erythorbate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464401285
| Reference = Merck Index, 11th Edition, 5009.{{cite web|url=https://scifinder.cas.org|title=CAS Registry Number 6381-77-7|publisher=SciFinder|access-date=14 November 2016}}{{cite PubChem|cid=23683938|title=Sodium erythorbate {{pipe}} C6H7NaO6 - PubChem|access-date=13 November 2022}}
| Name = Sodium erythorbate
| ImageFile = Sodium erythorbate.png
| ImageSize = 180px
| ImageName = Sodium erythorbate
| IUPACName = Sodium 1,4-anhydro-1-oxo-D-erythro-hex-2-enitol-3-O-ate
| SystematicName = Sodium (2R)-2-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate
| OtherNames = 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
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736142
| 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
| InChIKey = CIWBSHSKHKDKBQ-DUZGATOHBV
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51438
| SMILES = [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-]
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PPASLZSBLFJQEF-RKJRWTFHSA-M
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6381-77-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BZ468R6XRD
| PubChem = 23683938
| EINECS = 228-973-9
}}
| Section2 = {{Chembox Properties
| Formula = C6H7NaO6
| MolarMass = 198.11 g/mol
| Appearance = White crystalline solid
| Density = 1.2
| Solubility = 16 g/100 mL
| MeltingPtC = 168 to 170
| MeltingPt_notes =
| BoilingPt =
}}
| Section7 = {{Chembox Hazards
| ExternalSDS =
| MainHazards =
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
}}
}}
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, 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.[http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist Current EU approved additives and their E Numbers], Food Standards Agency
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.{{cite book|last=Hui|first=Y. H.|title=Handbook of Food Science, Technology and Engineering|publisher=CRC Press|year=2006|isbn=0-8493-9848-7|page=83-32}}
It is occasionally used in beverages, baked goods, and potato salad.{{cite book|title=Dictionary of Food Ingredients|url=https://archive.org/details/dictionaryfoodin00igoe_762|url-access=limited|last=Igoe|first=R. S.|publisher=Springer US|year=2011|location=Boston, MA|pages=[https://archive.org/details/dictionaryfoodin00igoe_762/page/n137 129]|isbn=9781441997128 }}
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 metalsChristensen RJ, Steimel LH, Oxygen scavenger for boiler water and method of use. US patent 4,891,141. 1990 and it has been implemented in active packaging.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. 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.{{cite journal |last1=Silveira Alexandre |first1=Ana Cláudia |last2=Corrêa Albergaria |first2=Francielly |last3=dos Santos Ferraz e Silva |first3=Lara Maria |last4=Carneiro Fernandes |first4=Luíza Aparecida |last5=de Sousa Gomes |first5=Maria Emília |last6=Pimenta |first6=Carlos José |date=15 January 2022 |title=Effect of natural and synthetic antioxidants on oxidation and storage stability of mechanically separated tilapia meat |journal=LWT - Food Science and Technology |volume=154 |pages=112679 |doi=10.1016/j.lwt.2021.112679 |doi-access=free }}
Production
{{main|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.{{cite web
|url = http://www.pmpinc.com/products/SodiumErythorbate.asp
|title = Sodium Erythorbate
|publisher = PMP Fermentation Products, Inc.
|access-date = 2008-10-27
|url-status = dead
|archive-url = https://web.archive.org/web/20100111071932/http://www.pmpinc.com/products/SodiumErythorbate.asp
|archive-date = January 11, 2010
}}{{cite web|url=http://www.pmpinc.com/Products/SodiumErythorbate.asp |title=Sodium Erythorbate (Archive Copy - Original not available?) |publisher=PMP Fermentation Products, Inc. |access-date=2011-10-23 |url-status=unfit |archive-url=https://web.archive.org/web/20100111071932/http://www.pmpinc.com/Products/SodiumErythorbate.asp |archive-date=January 11, 2010 }}{{cite web | url = http://www.chemicalbook.com/ChemicalProductProperty_EN_CB9421390.htm | title = Sodium erythorbate}} The glucose is converted to a 2-keto sugar acid intermediate, most commonly 2-keto-D-gluconic acid, by Pseudomonas fluorescens bacteria.{{cite journal |last=Andersen |first=FA |date=1999 |title=Final Report on the Safety Assessment of Ascorbyl Palmitate, Ascorbyl Dipalmitate, Ascorbyl Stearate, Erythorbic Acid, and sodium Erythorbate. |url=https://journals.sagepub.com/doi/10.1177/109158189901800303 |journal=International Journal of Toxicology |volume=18(3_suppl) |issue=3_suppl |pages=1–26 |doi=10.1177/109158189901800303 |s2cid=85834903 |access-date=13 November 2022 |via=SAGE Publishing|url-access=subscription }}
An urban myth claims that sodium erythorbate is made from ground earthworms; however, there is no truth to the myth.[http://library.state.or.us/repository/2010/201005111549522/index.pdf Sodium Erythorbate - is it an earthworm?], Oregon Department of Agriculture It is thought that the origin of the legend comes from the similarity of the chemical name to the words earthworm and bait.
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.{{cite book|title=The Merck Index|publisher=Merck Research Laboratories|year=2006|edition=14th |pages=Page 890, section 5126}} 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.
References
{{reflist}}
{{sodium compounds}}