Sodium ascorbate

Last updated

Sodium l-ascorbate [1]
Sodium ascorbate.png
Sodium ascorbate powder.jpg
Names
IUPAC name
Sodium (2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2H-furan-3-olate
Other names
Sodascorbate; Monosodium ascorbate; E301
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ECHA InfoCard 100.004.661 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-126-1
E number E301 (antioxidants, ...)
KEGG
PubChem CID
RTECS number
  • CI7671000
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+;/m0./s1
  • OC1=C([O-])[C@]([C@@H](O)CO)([H])OC1=O.[Na+]
Properties
C6H7NaO6
Molar mass 198.106 g·mol−1
Appearanceminute white to yellow crystals
Odor odorless
Density 1.66 g/cm3
Melting point 218 °C (424 °F; 491 K) (decomposes)
62 g/100 mL (25 °C)
78 g/100 mL (75 °C)
Solubility very slightly soluble in alcohol
insoluble in chloroform, ether
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sodium ascorbate is one of a number of mineral salts of ascorbic acid (vitamin C). The molecular formula of this chemical compound is C6H7NaO6. As the sodium salt of ascorbic acid, it is known as a mineral ascorbate. It has not been demonstrated to be more bioavailable than any other form of vitamin C supplement. [2]

Contents

Sodium ascorbate normally provides 131 mg of sodium per 1,000 mg of ascorbic acid (1,000 mg of sodium ascorbate contains 889 mg of ascorbic acid and 111 mg of sodium).

As a food additive, it has the E number E301 and is used as an antioxidant and an acidity regulator. It is approved for use as a food additive in the EU, [3] USA, [4] Australia, and New Zealand. [5]

In in vitro studies, sodium ascorbate has been found to produce cytotoxic effects in various malignant cell lines, which include melanoma cells that are particularly susceptible. [6] [7]

Production

Sodium ascorbate is produced by dissolving ascorbic acid in water and adding an equivalent amount of sodium hydroxide or sodium bicarbonate in water. After cessation of effervescence, the sodium ascorbate is precipitated by the addition of isopropanol.

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
6H
8O
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.

Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants are frequently added to industrial products, such as polymers, fuels, and lubricants, to extend their usable lifetimes. Foods are also treated with antioxidants to forestall spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol, or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress.

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.

<span class="mw-page-title-main">Vitamin C</span> Essential nutrient found in citrus fruits and other foods

Vitamin C is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription dietary supplement. As a therapy, it is used to prevent and treat scurvy, a disease caused by vitamin C deficiency.

<span class="mw-page-title-main">E number</span> Codes for food additives

E numbers, short for Europe numbers, are codes for substances used as food additives, including those found naturally in many foods, such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly found on food labels, their safety assessment and approval are the responsibility of the European Food Safety Authority (EFSA). The fact that an additive has an E number implies that its use was at one time permitted in products for sale in the European Single Market; some of these additives are no longer allowed today.

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

Pantothenic acid (vitamin B5) is a B vitamin and an essential nutrient. All animals need pantothenic acid in order to synthesize coenzyme A (CoA), which is essential for cellular energy production and for the synthesis and degradation of proteins, carbohydrates, and fats.

<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">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.

Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid. It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbic acid by glutathione and other thiols. The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids.

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

Sodium propanoate or sodium propionate is the sodium salt of propionic acid which has the chemical formula Na(C2H5COO). This white crystalline solid is deliquescent in moist air.

<span class="mw-page-title-main">Ponceau 4R</span> Chemical compound

Ponceau 4R is a synthetic colourant that may be used as a food colouring. It is denoted by E Number E124. Its chemical name is 1-(4-sulfo-1-napthylazo)-2-napthol-6,8-disulfonic acid, trisodium salt. Ponceau is the generic name for a family of azo dyes.

<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">Ascorbyl palmitate</span> Chemical compound

Ascorbyl palmitate is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C. In addition to its use as a source of vitamin C, it is also used as an antioxidant food additive. It is approved for use as a food additive in the EU, the U.S., Canada, Australia, and New Zealand.

Ascorbyl stearate (C24H42O7) is an ester formed from ascorbic acid and stearic acid. In addition to its use as a source of vitamin C, it is used as an antioxidant food additive in margarine (E number E305). The USDA limits its use to 0.02% individually or in conjunction with other antioxidants.

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

Calcium ascorbate is a compound with the molecular formula CaC12H14O12. It is the calcium salt of ascorbic acid, one of the mineral ascorbates. It is approximately 10% calcium by mass.

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

Potassium ascorbate is a compound with formula KC6H7O6. It is the potassium salt of ascorbic acid (vitamin C) and a mineral ascorbate. As a food additive, it has E number E303, INS number 303. Although it is not a permitted food additive in the UK, USA and the EU, it is approved for use in Australia and New Zealand. According to some studies, it has shown a strong antioxidant activity and antitumoral properties.

<span class="mw-page-title-main">Dough conditioner</span> Substance added to bread dough to strengthen its texture

A dough conditioner, flour treatment agent, improving agent or bread improver is any ingredient or chemical added to bread dough to strengthen its texture or otherwise improve it in some way. Dough conditioners may include enzymes, yeast nutrients, mineral salts, oxidants and reductants, bleaching agents and emulsifiers. They are food additives combined with flour to improve baking functionality. Flour treatment agents are used to increase the speed of dough rising and to improve the strength and workability of the dough.

Vitamin B<sub>3</sub> Class of chemically related vitamers

Vitamin B3, colloquially referred to as niacin, is a vitamin family that includes three forms, or vitamers: niacin (nicotinic acid), nicotinamide (niacinamide), and nicotinamide riboside. All three forms of vitamin B3 are converted within the body to nicotinamide adenine dinucleotide (NAD). NAD is required for human life and people are unable to make it within their bodies without either vitamin B3 or tryptophan. Nicotinamide riboside was identified as a form of vitamin B3 in 2004.

<span class="mw-page-title-main">Intravenous ascorbic acid</span> Nonmedical procedure

Intravenous Ascorbic Acid or PAA, pharmacologic ascorbic acid, is a process that delivers soluble ascorbic acid directly into the bloodstream. It is not approved for use to treat any medical condition.

References

  1. ↑ (+)-Sodium L-ascorbate at Sigma-Aldrich
  2. ↑ Linus Pauling Institute, Oregon State University: "Bioavailability of Different Forms of Vitamin C" . Retrieved 2013-09-27.
  3. ↑ UK Food Standards Agency: "Current EU approved additives and their E Numbers" . Retrieved 2011-10-27.
  4. ↑ US Food and Drug Administration: "Listing of Food Additives Status Part II". Food and Drug Administration . Retrieved 2011-10-27.
  5. ↑ Australia New Zealand Food Standards Code "Standard 1.2.4 - Labelling of ingredients". 8 September 2011. Retrieved 2011-10-27.
  6. ↑ Chen Q, Espey MG, Krishna MC, Mitchell JB, Corpe CP, Buettner GR, Shacter E, Levine M (September 2005). "Pharmacologic ascorbic acid concentrations selectively kill cancer cells: Action as a pro-drug to deliver hydrogen peroxide to tissues". Proc Natl Acad Sci U S A. 102 (38): 13604–9. Bibcode:2005PNAS..10213604C. doi: 10.1073/pnas.0506390102 . PMC   1224653 . PMID   16157892.
  7. ↑ Kang JS, Cho D, Kim YI, Hahm E, Kim YS, Jin SN, Kim HN, Kim D, Hur D, Park H, Hwang YI, Lee WJ (July 2005). "Sodium ascorbate (vitamin C) induces apoptosis in melanoma cells via the down-regulation of transferrin receptor dependent iron uptake". J. Cell. Physiol. 204 (1): 192–7. doi: 10.1002/jcp.20286 . PMID   15672419. S2CID   28597142.
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