134-03-2

Basic information

• Product Name: Sodium ascorbate
• Synonyms: ASCORBIC ACID SODIUM SALT;L(+)-ASCORBIC ACID SODIUM SALT;L-ASCORBIC ACID SODIUM SALT;L-ASCORBIC ACID NA-SALT;MONOSODIUM L-ASCORBATE;SODIUM L(+)-ASCORBATE;SODIUM L-ASCORBATE;SODIUM 5-(1,2-DIHYDROXYETHYL)-3-HYDROXY-4-OXO-FURAN-2-OLATE
• CAS NO: 134-03-2
• Molecular Formula: C₆H₇O₆*Na
• Molecular Weight: 198.11
• EINECS: 205-126-1
• Product Categories: Food and Feed Additive;Antioxidant;Biochemistry;Sugar Acids;Sugars;Vitamins;Vitamins and derivatives;Inhibitors
• Mol File: 134-03-2.mol

Chemical Properties

• Melting Point: 220 °C (dec.)(lit.)
• Boiling Point: 552.7 °C at 760 mmHg
• Flash Point: 238.2 °C
• Appearance: white to slightly yellow/powder
• Density: 1.799 g/cm3
• Vapor Pressure: 1.62E-14mmHg at 25°C
• Refractive Index: 105.5 ° (C=10, H2O)
• Storage Temp.: Store at RT.
• Solubility: H2O: 50 mg/mL
• Water Solubility: 620 g/L (20 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,830
• BRN: 3767246
• CAS DataBase Reference: Sodium ascorbate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium ascorbate(134-03-2)
• EPA Substance Registry System: Sodium ascorbate(134-03-2)

Safety Data

• Statements: 68
• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: CI7671000
• TSCA: Yes
• Hazardous Substances Data: 134-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Manufacturing:
Sodium ascorbate is used as an antioxidant and acidity regulator in pharmaceutical manufacturing. It helps to prevent the oxidation of sensitive compounds and maintains a stable pH level in the production process.
Used in the Food Industry:
Sodium ascorbate is used as an antioxidant and acidity regulator in the food industry. It helps to prevent the oxidation of food components, maintaining freshness and extending the shelf life of various products.
Used in Cell Culture:
Sodium ascorbate is used as a reducing agent in cell culture applications, helping to reduce oxidative stress and maintain a healthy environment for cell growth.
Used as an Antimicrobial and Antioxidant in Foodstuffs:
Sodium ascorbate is used to inhibit the growth of microorganisms and prevent oxidation in various food products, enhancing their quality and safety.
Used in Cancer Prevention and Treatment:
Studies have shown that taking sodium ascorbate is helpful for cancer prevention and treatment, making it a valuable supplement for those at risk or undergoing cancer treatment.
Used in Vitamin C Supplementation:
As a vitamin C supplement, sodium ascorbate provides both sodium and vitamin C for the human body, which is effective in preventing or treating vitamin C deficiency and may be easier to tolerate for individuals with sensitive digestive systems.
Used in Flour Treatment:
Sodium ascorbate is used as a flour treatment agent, improving the quality and texture of baked goods.
Used as a Coenzyme, Plant Metabolite, Human Metabolite, and Reducing Agent:
Sodium ascorbate has various roles in biological systems, including acting as a coenzyme, plant metabolite, human metabolite, Daphnia magna metabolite, and reducing agent.

References

https://en.wikipedia.org/wiki/Sodium_ascorbate http://www.livestrong.com/article/348175-what-are-the-health-benefits-of-sodium-ascorbate/ http://pets.webmd.com/drugs/2/drug-63684/ascorbic-acid-ascorbate-sodium-oral/details

Production Methods

An equivalent amount of sodium bicarbonate is added to a solution of ascorbic acid in water. Following the cessation of effervescence, the addition of propan-2-ol precipitates sodium ascorbate.

Air & Water Reactions

Water soluble. Aqueous solutions are subject to quick air oxidation at pH greater than 6.0.

Reactivity Profile

A weak base. Materials in this group are generally soluble in water. The resulting solutions contain moderate concentrations of hydroxide ions and have pH's greater than 7.0. They react as bases to neutralize acids. These neutralizations generate heat, but less or far less than is generated by neutralization of the bases in reactivity group 10 (Bases) and the neutralization of amines. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible.

Health Hazard

SYMPTOMS: Ingestion of 10 grams or more of this type of compound may cause diarrhea.

Fire Hazard

Flash point data for Sodium ascorbate are not available. Sodium ascorbate is probably combustible.

Flammability and Explosibility

Notclassified

Pharmaceutical Applications

Sodium ascorbate is used as an antioxidant in pharmaceutical formulations, and also in food products where it increases the effectiveness of sodium nitrite against growth of Listeria monocytogenes in cooked meats. It improves gel cohesiveness and sensory firmness of fiberized products regardless of vacuum treatment. It is also used therapeutically as a source of vitamin C in tablets and parenteral preparations.

Biochem/physiol Actions

Ascorbic acid exhibits anti-oxidant properties. It is a primary substrate for detoxifying hydrogen peroxide. Ascorbic acid is a co-factor for the synthesis of adrenal steroids and catecholamines. L-Ascorbic acid (Vitamin C) is a water soluble molecule used in a wide variety of applications, including cell culture, as a reducing agent that helps reduce oxidative stress. L-Ascorbate can be regenerated by biological systems.

Safety Profile

Human mutation data reported. When heated to decomposition it emits toxic fumes of Na2O.

Safety

The parenteral administration of 0.25-1.00 g of sodium ascorbate, given daily in divided doses, is recommended in the treatment of vitamin C deficiencies. Various adverse reactions have been reported following the administration of 1 g or more of sodium ascorbate, although ascorbic acid and sodium ascorbate are usually well tolerated; see Ascorbic acid. There have been no reports of adverse effects associated with the much lower concentrations of sodium ascorbate and ascorbic acid, which are employed as antioxidants. The WHO has set an acceptable daily intake of ascorbic acid, potassium ascorbate, and sodium ascorbate, as antioxidants in food, at up to 15 mg/kg body-weight in addition to that naturally present in food.

storage

Sodium ascorbate is relatively stable in air, although it gradually darkens on exposure to light. Aqueous solutions are unstable and subject to rapid oxidation in air at pH > 6.0. The bulk material should be stored in a well-closed nonmetallic container, protected from light, in a cool, dry place.

Incompatibilities

Incompatible with oxidizing agents, heavy metal ions, especially copper and iron, methenamine, sodium nitrite, sodium salicylate, and theobromine salicylate. The aqueous solution is reported to be incompatible with stainless steel filters.

Regulatory Status

GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IV preparations; oral tablets). Included in nonparenteral and parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

InChI:InChI=1/C6H8O6.Na/c7-1-2(8)5-3(9)4(10)6(11)12-5;/h2,5,7-10H,1H2;/q;+1/p-1

Synthetic route

sodium ascorbate (134-03-2) + dichlorodiethylstannane (866-55-7) → Sn(4+)*2C2H5(1-)*C6H6O6(2-)*H2O=Sn(C2H5)2(C6H6O6)*H2O

Conditions	Yield
In methanol (N2); dropwise addn. of the Sn-compound in MeOH to a suspension of ascorbate in MeOH with stirring at 0°C; after allowing to warm up to room temp. the mixt. is heated under reflux for 3 h; volatiles are removed in vac. and the solid is successively washed with CH2Cl2 and THF and water, recrystn. from MeOH; elem. anal.;	85%

dimethyltin dichloride (753-73-1) + sodium ascorbate (134-03-2) → Sn(CH3)2(C6H6O6)*H2O

Conditions	Yield
In methanol (N2;) dropwise addn. of Sn compound in MeOH to a suspension of ascorbate in MeOH with stirring at 0°C; after allowing to warm up to room temp. the mixt. is heated under reflux for 3.5 h; volatiles are removed in vac. and the solid is successively washed with CH2Cl2 and THF, recrystn. from MeOH; elem. anal.;	73%

sodium ascorbate (134-03-2) + diphenyltin(IV) dichloride (1135-99-5) → [Ph2Sn(L-ascorbic acid(-2H))]

Conditions	Yield
In methanol byproducts: NaCl; (N2); soln. of Sn compd. (1 equiv.) in methanol was added dropwise with stirring to suspn. of ascorbate (2 equiv.) in methanol at 0°C; soln. was warmed to room temp.; refluxed for 3 h; filtered; concd. (vac.); washed (CH2Cl2); recrystd. (methanol); elem. anal.;	50%

sodium ascorbate (134-03-2) + triphenyltin chloride (639-58-7) → [Ph3Sn(L-ascorbate)]

Conditions	Yield
In methanol byproducts: NaCl; (N2); soln. of Sn compd. (1 equiv.) in methanol was added dropwise with stirring to suspn. of ascorbate (1 equiv.) in methanol; soln. was stirred at room temp. for 10 min; refluxed for 6 h; filtered; volatiles removed (vac.); washed (CH2Cl2); dried (vac.); recrystd. (methanol); elem. anal.;	47%

bis(cyclopentadienyl)titanium dichloride (1271-19-8) + sodium ascorbate (134-03-2) → {(C5H5)2Ti(C6H7O6)2}

Conditions	Yield
In water (N2); dropwise addn. of a soln. of ascorbate in water to a soln. of the Ti-compd. in water with stirring at 10°C, stirring of the mixt. for 2 h; allowing to warm slowly up to room temp.;; ppt. is collected by filtn., washed with cooled water and redissolved in THF, pptn. by addn. of hexane; elem. anal.;	45%

tributyltin chloride (1461-22-9) + sodium ascorbate (134-03-2) → [(n-Bu)3Sn(L-ascorbate)]

Conditions	Yield
In methanol byproducts: NaCl; (N2); soln. of Sn compd. (1 equiv.) in methanol was added dropwise with stirring to suspn. of ascorbate (1 equiv.) in methanol; soln. was stirred at room temp. for 10 min; refluxed for 6 h; filtered; volatiles removed (vac.); washed (CH2Cl2); dried (vac.); recrystd. (methanol); elem. anal.;	23%

trimethyltin(IV)chloride (1066-45-1) + sodium ascorbate (134-03-2) → [Me3Sn(L-ascorbate)]

Conditions	Yield
In methanol byproducts: NaCl; (N2); soln. of Sn compd. (1 equiv.) in methanol was added dropwise with stirring to suspn. of ascorbate (1 equiv.) in methanol; soln. was stirred at room temp. for 10 min; refluxed for 6 h; filtered; volatiles removed (vac.); washed (CH2Cl2); dried (vac.); recrystd. (methanol); elem. anal.;	20%

dibutyltin chloride (683-18-1) + sodium ascorbate (134-03-2) → [(n-Bu)2Sn(L-ascorbic acid(-2H))]

Conditions	Yield
In methanol byproducts: NaCl; (N2); soln. of Sn compd. (1 equiv.) in methanol was added dropwise with stirring to suspn. of ascorbate (2 equiv.) in methanol at 0°C; soln. was warmed to room temp.; refluxed for 3 h; filtered; concd. (vac.); washed (CH2Cl2); recrystd. (methanol); elem. anal.;	20%

sodium ascorbate (134-03-2) + tripropyltin chloride (2279-76-7) → [(n-Pr)3Sn(L-ascorbate)]

Conditions	Yield
In methanol byproducts: NaCl; (N2); soln. of Sn compd. (1 equiv.) in methanol was added dropwise with stirring to suspn. of ascorbate (1 equiv.) in methanol; soln. was stirred at room temp. for 10 min; refluxed for 6 h; filtered; volatiles removed (vac.); washed (CH2Cl2); dried (vac.); recrystd. (methanol); elem. anal.;	20%

sodium ascorbate (134-03-2) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
rat intestinal (or rice seed) α-glucosidase, maltose, thiourea, 0.1 M acetate buffer, 3 h, 50 deg C, in the dark;	14%

sodium ascorbate (134-03-2) + alpha cyclodextrin (10016-20-3) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
Stage #1: sodium ascorbate; alpha cyclodextrin With cyclodextrin glucanotransferase from Thermoanaerobacter sp. In aq. acetate buffer at 40℃; for 24h; pH=4.0; Enzymatic reaction; Stage #2: With amyloglucosidase from Aspergillus niger In aq. acetate buffer at 60℃; for 2h; Enzymatic reaction; regioselective reaction;	0.27%

sodium ascorbate (134-03-2) + β‐cyclodextrin (7585-39-9) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
Stage #1: sodium ascorbate; β‐cyclodextrin With cyclodextrin glucanotransferase from Thermoanaerobacter sp. In aq. acetate buffer at 40℃; for 24h; pH=4.0; Enzymatic reaction; Stage #2: With amyloglucosidase from Aspergillus niger In aq. acetate buffer at 60℃; for 2h; Enzymatic reaction; regioselective reaction;	0.24%

sodium ascorbate (134-03-2) + cyclomaltooctaose (17465-86-0) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
Stage #1: sodium ascorbate; cyclomaltooctaose With cyclodextrin glucanotransferase from Thermoanaerobacter sp. In aq. acetate buffer at 40℃; for 24h; pH=4.0; Enzymatic reaction; Stage #2: With amyloglucosidase from Aspergillus niger In aq. acetate buffer at 60℃; for 2h; Enzymatic reaction; regioselective reaction;	0.21%

Maltose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 6363-53-7) + sodium ascorbate (134-03-2) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
With acetate buffer; rice seed α-glucosidase; thiourea at 50℃; for 5h;

water (7732-18-5) + sodium ascorbate (134-03-2) + oxygen + alkaline solution → oxalic acid (144-62-7) + L-threonic acid-4-lactone (21730-93-8)

Conditions	Yield
Behandeln des Natrium-Salzes oder anderer Alkalisalze;

sodium metaborate (7775-19-1) + sodium ascorbate (134-03-2) → 3Na(1+)*{B(C6H5O6)2}(3-)*3H2O=Na3{B(C6H5O6)2}*3H2O

Conditions	Yield
In not given pptg. with methanol;
In not given pptg. with methanol;

sodium ascorbate (134-03-2) + ascorbic acid (50-81-7) → hydrogen (1333-74-0)

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; C18H23N3NiS3(2+)*2ClO4(1-) In N,N-dimethyl acetamide; water pH=4; Catalytic behavior; Irradiation;

Upstream product

• 144-55-8 sodium hydrogencarbonate 
• 50-81-7 ascorbic acid 
• 7632-00-0 sodium nitrite 
• 1071558-27-4 (3R,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxo-hexanoic acid methyl ester 
• 71-36-3 butan-1-ol 
• 3031-98-9 L-xylo-[2]hexulosonic acid methyl ester 
• 2797-51-5 quinoclamine 

Downstream Products

• 129499-78-1 2-O-α-D-glucopyranosyl L-ascorbate 
• 112680-45-2 3-O-benzylisoascorbic acid 
• 15667-21-7 D-erythronolactone 
• 107706-92-3 (R)-4-Benzyloxy-5-((R)-1,2-dihydroxy-ethyl)-3-octadecyloxy-5H-furan-2-one 
• 98-01-1 furfural 
• 7306-96-9 L-threonic acid 
• 144-62-7 oxalic acid 
• 137460-62-9 methyl (2R,3S)-2,3,4-trihydroxybutanoate 
• 21730-93-8 L-threonic acid-4-lactone 
• 167095-80-9 3-O-retinoyl-L-ascorbic acid 
• 50-81-7 ascorbic acid 
• 123-31-9 hydroquinone 
• 52179-26-7 (-)-4-(2,2-dichlorocyclopropyl)phenol 
• 76003-76-4 1-benzyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester 

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In the process described for the production of sodium or potassium L-ascorbate, 2-keto-L-gulonic acid monhydrate is esterified with methanol. The esterification is only partial, that is, is not carried out until the esterification equilibrium is reached.

Ascorbic acid process

An improved process for the preparation of ascorbic acid and erythorbic acid is disclosed, the improvement comprising the removal of borate impurities from a 2-ketogulonate and a 2-ketogluconate prior to formation of the desired acids by base catalyzed cyclization.