Sodium erythorbate

Last updated
Sodium erythorbate [1] [2] [3]
Sodium erythorbate.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 228-973-9
E number E316 (antioxidants, ...)
PubChem CID
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 X mark.svgN
    Key: PPASLZSBLFJQEF-RKJRWTFHSA-M X mark.svgN
  • 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
AppearanceWhite 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.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

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]

Related Research Articles

<span class="mw-page-title-main">Chemistry of ascorbic acid</span> Chemical compound

Ascorbic acid is an organic compound with formula C
6
H
8
O
6
, originally called hexuronic acid. It is a white solid, but impure samples can appear yellowish. It dissolves freely in water to give mildly acidic solutions. It is a mild reducing agent.

<span class="mw-page-title-main">Food preservation</span> Inhibition of microbial growth in food

Food preservation includes processes that make food more resistant to microorganism growth and slow the oxidation of fats. This slows down the decomposition and rancidification process. Food preservation may also include processes that inhibit visual deterioration, such as the enzymatic browning reaction in apples after they are cut during food preparation. By preserving food, food waste can be reduced, which is an important way to decrease production costs and increase the efficiency of food systems, improve food security and nutrition and contribute towards environmental sustainability. For instance, it can reduce the environmental impact of food production.

A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.

Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.

<span class="mw-page-title-main">Sulfite</span> Oxyanion with a central atom of sulfur surrounded by 3 oxygen atoms

Sulfites or sulphites are compounds that contain the sulfite ion, SO2−
3
. The sulfite ion is the conjugate base of bisulfite. Although its acid is elusive, its salts are widely used.

<span class="mw-page-title-main">Sodium benzoate</span> Chemical compound

Sodium benzoate also known as benzoate of soda is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C6H5COONa.

<span class="mw-page-title-main">Sodium sulfite</span> Chemical compound

Sodium sulfite (sodium sulphite) is the inorganic compound with the chemical formula Na2SO3. A white, water-soluble solid, it is used commercially as an antioxidant and preservative. It is also suitable for the softening of lignin in the pulping and refining processes of wood and lignocellulosic materials. A heptahydrate is also known but it is less useful because of its greater susceptibility toward oxidation by air.

<span class="mw-page-title-main">Erythorbic acid</span> Chemical compound

Erythorbic acid is a stereoisomer of ascorbic acid. 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. It is denoted by E number E315, and is widely used as an antioxidant in processed foods.

<span class="mw-page-title-main">Potassium metabisulfite</span> Chemical compound

Potassium metabisulfite, K2S2O5, also known as potassium pyrosulfite, is a white crystalline powder with a pungent odour. It is mainly used as an antioxidant or chemical sterilant. As a disulfite, it is chemically very similar to sodium metabisulfite, with which it is sometimes used interchangeably. Potassium metabisulfite has a monoclinic crystal structure.

<span class="mw-page-title-main">Potassium sorbate</span> Chemical compound

Potassium sorbate is the potassium salt of sorbic acid, chemical formula CH3CH=CH−CH=CH−CO2K. It is a white salt that is very soluble in water (58.2% at 20 °C). It is primarily used as a food preservative (E number 202). Potassium sorbate is effective in a variety of applications including food, wine, and personal-care products. While sorbic acid occurs naturally in rowan and hippophae berries, virtually all of the world's supply of sorbic acid, from which potassium sorbate is derived, is manufactured synthetically.

<span class="mw-page-title-main">Mineral ascorbates</span>

Mineral ascorbates are a group of salts of ascorbic acid. They are composed of a mineral cation bonded to ascorbate.

<span class="mw-page-title-main">Calcium sulfite</span> Chemical compound

Calcium sulfite, or calcium sulphite, is a chemical compound, the calcium salt of sulfite with the formula CaSO3·x(H2O). Two crystalline forms are known, the hemihydrate and the tetrahydrate, respectively CaSO3·½(H2O) and CaSO3·4(H2O). All forms are white solids. It is most notable as the product of flue-gas desulfurization.

<span class="mw-page-title-main">Disulfite</span> Chemical compound

A disulfite, commonly known as metabisulfite or pyrosulfite, is a chemical compound containing the ion S
2
O2−
5
. It is a colorless dianion that is primarily marketed in the form of sodium metabisulfite or potassium metabisulfite. When dissolved in water, these salts release the hydrogensulfite HSO
3
anion. These salts act equivalently to sodium hydrogensulfite or potassium hydrogensulfite.

Warmed-over flavor is an unpleasant characteristic usually associated with meat which has been cooked and then refrigerated. The deterioration of meat flavor is most noticeable upon reheating. As cooking and subsequent refrigeration is the case with most convenience foods containing meat, it is a significant challenge to the processed food industry. The flavor is variously described as "rancid," "stale," and like "cardboard," and even compared to "damp dog hair." Warmed-over flavor is caused by the oxidative decomposition of lipids in the meat into chemicals which have an unpleasant taste or odor. This decomposition process begins after cooking or processing and is aided by the release of naturally occurring iron in the meat.

<span class="mw-page-title-main">Potassium erythorbate</span> Chemical compound

Potassium erythorbate (C6H7KO6) is a food additive. Chemically, it is the potassium salt of erythorbic acid. As an antioxidant structurally related to vitamin C, it helps improve flavor stability and prevents the formation of carcinogenic nitrosamines.

<span class="mw-page-title-main">Ammonium sulfite</span> Chemical compound

Ammonium sulfite is the ammonium salt of sulfurous acid with the chemical formula (NH4)2SO3.

<span class="mw-page-title-main">Sodium bisulfite</span> Chemical compound

Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of sodium and bisulfite ions. It appears in form of white or yellowish-white crystals with an odor of sulfur dioxide. Regardless of its ill-defined nature, sodium bisulfite is used in many different industries such as a food additive with E number E222 in the food industry, a reducing agent in the cosmetic industry, and a decomposer of residual hypochlorite used in the bleaching industry.

<span class="mw-page-title-main">Wine preservatives</span> Food preservation

Wine preservatives are used to preserve the quality and shelf life of bottled wine without affecting its taste. Specifically, they are used to prevent oxidation and bacterial spoilage by inhibiting microbial activity.

The topic of sulfite food and beverage additives covers the application of sulfites in food chemistry. "Sulfite" is jargon that encompasses a variety of materials that are commonly used as preservatives or food additive in the production of diverse foods and beverages. Although sulfite salts are relatively nontoxic, their use has led to controversy, resulting in extensive regulations. Sulfites are a source of sulfur dioxide (SO2), a bactericide.

References

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  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. 1 2 Igoe, R. S. (2011). Dictionary of Food Ingredients . Boston, MA: Springer US. pp.  129. ISBN   9781441997128.
  7. "Sodium Erythorbate". PMP Fermentation Products, Inc. Archived from the original on January 11, 2010. Retrieved 2008-10-27.
  8. "Sodium Erythorbate (Archive Copy - Original not available?)". 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. 1 2 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. 1 2 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.