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59-30-3

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59-30-3 Usage

Description

Folic acid, also known as folate or vitamin B9, is an essential B-vitamin that plays a crucial role in various biological processes, including nucleotide synthesis, DNA synthesis and repair, and amino acid metabolism. It is a water-soluble vitamin that aids in the formation of red blood cells, prevents certain anemias, and is essential in normal metabolism. Folic acid is found in liver, nuts, and green vegetables, and is often synthesized for dietary supplementation.

Uses

Used in Pharmaceutical Industry:
Folic acid is used as a hematopoietic vitamin, which aids in the formation of red blood cells and prevents certain anemias. It is essential for normal metabolism and is involved in the metabolism of some amino acids needed for protein synthesis.
Used in Cosmetics Industry:
Folic acid is used as an emollient in the cosmetics industry. It has been shown to aid in DNA synthesis and repair, promote cellular turnover, reduce wrinkles, and promote skin firmness. There is some indication that folic acid may also protect DNA from UV-induced damage.
Used in Nutritional Supplements:
Folic acid is used as a nutritional supplement to prevent deficiency, which can lead to a range of developmental and cognitive disorders, most prominently neural tube defects and congenital heart defects. It is especially important during periods of rapid cell division, such as in pregnancy.
Used in Anticancer Applications:
Folic acid plays a role in the synthesis of aminopterin, a folate antagonist, which was one of the first anticancer drugs produced. Aminopterin and methotrexate, derivatives of folic acid, are used as antineoplastic agents.
Used in Fertility and Pregnancy:
Folic acid plays an important role in fertility by contributing to spermatogenesis and can effectively prevent neural tube defects in babies during pregnancy. It also reduces the incidence of heart disease, stroke, and cancer.

Originator

Folvite, Lederle, US ,1946

Manufacturing Process

The following description is taken from US Patent 2,956,057. 100 grams of 1,3,3-trichloroacetone are heated on a boiling water bath and 95 grams of bromine are added thereto in drops while being stirred and the stirring is continued for about 1 hour. The resulting reaction solution is distilled under reduced pressure. 115 grams of 1-bromo-1,3,3- trichloroacetone are obtained having a boiling point of 85° to 95°C/17 mm (Hg). For the preparation of the hydrate, 100 grams of water are added to 100 grams of 1bromo-1,3,3-trichloroacetone, which is agitated and cooled. A white scaly crystal of hydrate of 1-bromo-1,3,3-trichloroacetone is obtained (100 grams), having a melting point of 52° to 53°C. 8.9 grams of 2,4,5-triamino-6-hydroxypyrimidine hydrochloride and 8 grams of p-aminobenzoylglutamic acid are dissolved in 400 cc warm water, which is cooled at 35° to 27°C and adjusted to pH 4 by using 20% caustic soda solution. To this solution was simultaneously added dropwise a solution obtained by dissolving 13.4 grams of 1-bromo-1,3,3-trichloroacetone hydrate in 90 cc of 50% methanol and 24 grams of 35% aqueous sodium bisulfite solution over a period of approximately 2 hours. During this period, in order to maintain the pH value of the reaction solution at 4 to 5, 20% caustic soda solution is added from time to time. The precipitate, formed by stirring for 5 hours after dropping was finished, is filtered, and the filtrated precipitate is refined; 5.6 grams of pure pteroylglutamic acid is obtained.

Therapeutic Function

Treatment of B vitamin (folacin) deficiency

Air & Water Reactions

Insoluble in water. Aqueous solutions have pHs of 4.0-4.8.

Reactivity Profile

Acid solutions of Folic acid are sensitive to heat, but towards neutrality, stability progressively increases. Solutions are inactivated by ultraviolet light and alkaline solutions are sensitive to oxidation. Folic acid is also inactivated by light. Folic acid is incompatible with oxidizing agents, reducing agents and heavy metal ions.

Fire Hazard

Flash point data for Folic acid are not available; however, Folic acid is probably combustible.

Biochem/physiol Actions

A nutritional delivery form of folate. Folic acid and its derivatives are essential mediators of one-carbon metabolism within cells.

Clinical Use

Folate-deficient megaloblastic anaemiaSupplement in HD patients

Safety Profile

Poison by intraperitoneal and intravenous routes. Experimental teratogenic effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Veterinary Drugs and Treatments

Folic acid is used to treat folic acid deficiency in dogs, cats, and horses (theoretically in other animal species as well) often due to small intestinal disease. Cats with exocrine pancreatic insufficiency appear to be most at risk for folate and cobalamin deficiencies secondary to malabsorption of folic acid in the diet. Dogs with exocrine pancreatic insufficiency often are noted to have increased folate levels secondary to overgrowths of folate-synthesizing bacteria in the proximal small intestine. Chronic administration of dihydrofolate reductase inhibiting drugs such as pyrimethamine, ormetoprim or trimethoprim can potentially lead to reduced activated folic acid (tetrahydrofolic acid); folic acid supplementation is sometimes prescribed in an attempt to alleviate this situation.

Drug interactions

Potentially hazardous interactions with other drugs Antiepileptics: reduces phenytoin, primidone and phenobarbital levels. Cytotoxics: avoid with raltitrexed.

Metabolism

Folic acid given therapeutically enters the portal circulation largely unchanged, since it is a poor substrate for reduction by dihydrofolate reductase. It is converted to the metabolically active form 5-methyltetrahydrofolate in the plasma and liver. Folate undergoes enterohepatic circulation. Folate metabolites are eliminated in the urine and folate in excess of body requirements is excreted unchanged in the urine.

Purification Methods

If paper chromatography indicates impurities, then recrystallise it from hot H2O or from dilute acid [Walker et al. J Am Chem Soc 70 19 1948]. Impurities may be removed by repeated extraction with n-BuOH of a neutral aqueous solution of folic acid (by suspending in H2O and adding N NaOH dropwise till the solid dissolves, then adjusting the pH to ~7.0-7.5) followed by precipitation with acid, filtration, or better collected by centrifugation and recrystallised form hot H2O. [Blakley Biochem J 65 331 1975, Kalifa et al. Helv Chim Acta 6 1 2739 1978.] Chromatography on cellulose followed by filtration through charcoal has also been used to obtain pure acid. [Sakami & Knowles Science 129 274 1959.] UV: max 247 and 296nm ( 12,800 and 18,700) in H2O pH 1.0; 282 and 346nm ( 27.600 and 7,200) in H2O pH 7.0; 256, 284 and 366nm ( 24600, 24,500 and 86,00) in H2O pH 13 [Rabinowitz in The Enzymes (Boyer et al. Eds), 2 185 1960]. [Beilstein 26 III/IV 3944.]

Check Digit Verification of cas no

The CAS Registry Mumber 59-30-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 59-30:
(4*5)+(3*9)+(2*3)+(1*0)=53
53 % 10 = 3
So 59-30-3 is a valid CAS Registry Number.
InChI:InChI=1/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/p-2/t12-/m1/s1

59-30-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (F0043)  Folic Acid Hydrate  >98.0%(HPLC)(T)

  • 59-30-3

  • 25g

  • 475.00CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1035)  Folicacid  pharmaceutical secondary standard; traceable to USP and PhEur

  • 59-30-3

  • PHR1035-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (F0300000)  Folicacid  European Pharmacopoeia (EP) Reference Standard

  • 59-30-3

  • F0300000-2EA

  • 1,880.19CNY

  • Detail
  • USP

  • (1286005)  Folicacid  United States Pharmacopeia (USP) Reference Standard

  • 59-30-3

  • 1286005-500MG

  • 4,662.45CNY

  • Detail
  • Supelco

  • (47866)  Folicacid  analytical standard

  • 59-30-3

  • 000000000000047866

  • 300.69CNY

  • Detail
  • Sigma-Aldrich

  • (F8798)  Folicacid  meets USP testing specifications

  • 59-30-3

  • F8798-5G

  • 424.71CNY

  • Detail
  • Sigma-Aldrich

  • (F8798)  Folicacid  meets USP testing specifications

  • 59-30-3

  • F8798-25G

  • 1,413.36CNY

  • Detail
  • Sigma-Aldrich

  • (F8798)  Folicacid  meets USP testing specifications

  • 59-30-3

  • F8798-100G

  • 5,270.85CNY

  • Detail

59-30-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name folic acid

1.2 Other means of identification

Product number -
Other names pteroic acid-glutamate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:59-30-3 SDS

59-30-3Synthetic route

N-(4-aminobenzoyl)-L-glutamic acid
4271-30-1

N-(4-aminobenzoyl)-L-glutamic acid

2,5,6-triamino-1,4-dihydropyrimidin-4-one hydrochloride

2,5,6-triamino-1,4-dihydropyrimidin-4-one hydrochloride

folate
59-30-3

folate

Conditions
ConditionsYield
With 1,1,1-trichloroacetone; sodium sulfite In water at 40 - 50℃; for 1h; pH=3 - 4; pH-value; Temperature;85%
1,1,3-trichloroacetone
921-03-9

1,1,3-trichloroacetone

N-(4-aminobenzoyl)-L-glutamic acid
4271-30-1

N-(4-aminobenzoyl)-L-glutamic acid

2,4,5-triamino-6-hydroxypyrimidine sulfate
35011-47-3

2,4,5-triamino-6-hydroxypyrimidine sulfate

folate
59-30-3

folate

Conditions
ConditionsYield
With sodium metabisulfite at 20 - 30℃; for 2h; Temperature; Ionic liquid;83.2%
With sodium metabisulfite; sodium acetate at 45℃; for 3h; Temperature;46.2%
1,1,1-trichloroacetone
918-00-3

1,1,1-trichloroacetone

p-Nitrobenzoyl-L-(+)-glutamic acid
6758-40-3

p-Nitrobenzoyl-L-(+)-glutamic acid

2,4-diamino-5-nitroso-6-hydroxypyrimidine
2387-48-6

2,4-diamino-5-nitroso-6-hydroxypyrimidine

folate
59-30-3

folate

Conditions
ConditionsYield
Stage #1: p-Nitrobenzoyl-L-(+)-glutamic acid; 2,4-diamino6-hydroxy-5-nitroso pyrimidine With hydrogen In water at 82℃; under 6000.6 Torr;
Stage #2: 1,1,1-trichloroacetone With sodium metabisulfite; sodium hydroxide In water at 45℃; pH=4.5; pH-value; Pressure; Temperature;
80%
1,1,1-trichloroacetone
918-00-3

1,1,1-trichloroacetone

N-(4-aminobenzoyl)-L-glutamic acid
4271-30-1

N-(4-aminobenzoyl)-L-glutamic acid

2,4,5-triamino-6-hydroxypyrimidine sulfate
35011-47-3

2,4,5-triamino-6-hydroxypyrimidine sulfate

folate
59-30-3

folate

Conditions
ConditionsYield
Stage #1: 1,1,1-trichloroacetone; N-(4-aminobenzoyl)-L-glutamic acid With sodium acetate; sodium sulfite In acetic acid at 43℃; for 0.5h;
Stage #2: 2,4,5-triamino-6-hydroxypyrimidine sulfate In acetic acid at 38℃; for 5h;
75.5%
1,1,3-tribromoacetone
3475-39-6

1,1,3-tribromoacetone

N-(4-aminobenzoyl)-L-glutamic acid
4271-30-1

N-(4-aminobenzoyl)-L-glutamic acid

2,4,5-triamino-6-hydroxypyrimidine sulfate
35011-47-3

2,4,5-triamino-6-hydroxypyrimidine sulfate

folate
59-30-3

folate

Conditions
ConditionsYield
With sodium carbonate In ethanol; water at 40℃; pH=7.5; Temperature; pH-value;60%
folate
65165-92-6

folate

2-hydroxy-3-oxopropionaldehyde
497-15-4

2-hydroxy-3-oxopropionaldehyde

N-(4-aminobenzoyl)-L-glutamic acid
4271-30-1

N-(4-aminobenzoyl)-L-glutamic acid

folate
59-30-3

folate

7,8-dihydrofolic acid
188497-71-4

7,8-dihydrofolic acid

Na-folate

Na-folate

sodium citrate
68-04-2

sodium citrate

folate
59-30-3

folate

Conditions
ConditionsYield
With sodium hydroxide
folinic acid
58-05-9

folinic acid

alpha cyclodextrin
10016-20-3

alpha cyclodextrin

folate
59-30-3

folate

Conditions
ConditionsYield
In water
folate
59-30-3

folate

N-tert-butoxycarbonyl cystamine
485800-26-8

N-tert-butoxycarbonyl cystamine

tert-butyl 2-{[2-({N2-(4-{[(2-amino-4-hydroxypteridin-6-yl)methyl]amino}benzoyl)-N1-[2-({2-[(tert-butoxycarbonyl)amino]ethyl}dithio)ethyl]-α-glutaminyl}amino)ethyl]dithio}ethylcarbamate
1301165-94-5

tert-butyl 2-{[2-({N2-(4-{[(2-amino-4-hydroxypteridin-6-yl)methyl]amino}benzoyl)-N1-[2-({2-[(tert-butoxycarbonyl)amino]ethyl}dithio)ethyl]-α-glutaminyl}amino)ethyl]dithio}ethylcarbamate

Conditions
ConditionsYield
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 100℃;96%
folate
59-30-3

folate

calcium chloride

calcium chloride

C19H17N7O6(2-)*Ca(2+)

C19H17N7O6(2-)*Ca(2+)

Conditions
ConditionsYield
Stage #1: folate With sodium hydroxide at 50℃; for 2h; pH=7.4;
Stage #2: calcium chloride In ethanol; water at 50℃; for 1h;
96%
folate
59-30-3

folate

strontium chloride

strontium chloride

C19H17N7O6(2-)*Sr(2+)

C19H17N7O6(2-)*Sr(2+)

Conditions
ConditionsYield
Stage #1: folate With sodium hydroxide at 50℃; for 2h; pH=7.4;
Stage #2: strontium chloride In ethanol; water at 50℃; for 1h;
95%
ethanol
64-17-5

ethanol

folate
59-30-3

folate

C23H27N7O6

C23H27N7O6

Conditions
ConditionsYield
With methanesulfonic acid at 20℃;95%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

folate
59-30-3

folate

N-hydroxysuccinimide folate
153445-05-7

N-hydroxysuccinimide folate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 24h; Darkness;94%
With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 0.0833333h; Inert atmosphere;53%
With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 50℃; for 6h;
1-amino-2-azidoethane
87156-40-9

1-amino-2-azidoethane

folate
59-30-3

folate

C21H23N11O5

C21H23N11O5

Conditions
ConditionsYield
Stage #1: folate With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dimethyl sulfoxide; N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Cooling with ice;
Stage #2: 1-amino-2-azidoethane In dimethyl sulfoxide; N,N-dimethyl-formamide at 0℃; for 2h; Inert atmosphere; Cooling with ice;
94%
Stage #1: folate With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; Inert atmosphere; Darkness;
Stage #2: 1-amino-2-azidoethane In dimethyl sulfoxide for 24h; Inert atmosphere; Darkness;
84%
folate
59-30-3

folate

Propargylamine
2450-71-7

Propargylamine

propargylfolate

propargylfolate

Conditions
ConditionsYield
Stage #1: folate With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: Propargylamine In N,N-dimethyl-formamide at 20℃; for 24h;
93%
folate
59-30-3

folate

butan-1-ol
71-36-3

butan-1-ol

C27H35N7O6

C27H35N7O6

Conditions
ConditionsYield
With methanesulfonic acid at 20℃;92%
formaldehyd
50-00-0

formaldehyd

folate
59-30-3

folate

calcium 5-methyl-tetrahydrofolate

calcium 5-methyl-tetrahydrofolate

Conditions
ConditionsYield
Stage #1: folate With sodium tetrahydroborate; edetate disodium; sodium hydroxide In water at 25 - 92℃;
Stage #2: formaldehyd With hydrogenchloride In water at 0 - 10℃; pH=9; Further stages;
91.35%
tert-butyl N-(6-aminohexyl)carbamate
51857-17-1

tert-butyl N-(6-aminohexyl)carbamate

folate
59-30-3

folate

γ-{[tert-butyl-N-(6-aminohexyl)]carbamate}folic acid
850754-81-3

γ-{[tert-butyl-N-(6-aminohexyl)]carbamate}folic acid

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 18h; Inert atmosphere;91%
folate
59-30-3

folate

Propargylamine
2450-71-7

Propargylamine

propargyl folic acid
1009599-12-5

propargyl folic acid

Conditions
ConditionsYield
Stage #1: folate With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: Propargylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;
90%
Stage #1: folate With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: Propargylamine In N,N-dimethyl-formamide at 25℃; for 24h;
71.2%
Stage #1: folate With 1-hydroxy-pyrrolidine-2,5-dione; 1,2-dichloro-ethane In N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: Propargylamine In N,N-dimethyl-formamide at 20℃; for 24h;
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

water
7732-18-5

water

hydrazine hydrate
7803-57-8

hydrazine hydrate

folate
59-30-3

folate

[Ni2(FA)(N2H4)3(H2O)2(OH-)2]

[Ni2(FA)(N2H4)3(H2O)2(OH-)2]

Conditions
ConditionsYield
Stage #1: nickel(II) chloride hexahydrate; water; folate In ethanol for 0.166667h; Sonication;
Stage #2: hydrazine hydrate In ethanol at 120℃; for 12h; pH=10.5; Autoclave;
90%
propan-1-ol
71-23-8

propan-1-ol

folate
59-30-3

folate

C25H31N7O6

C25H31N7O6

Conditions
ConditionsYield
With methanesulfonic acid at 20℃;89%
methanol
67-56-1

methanol

folate
59-30-3

folate

C21H23N7O6
319919-60-3

C21H23N7O6

Conditions
ConditionsYield
With methanesulfonic acid at 20℃;87%
adamantylmethylamine
17768-41-1

adamantylmethylamine

folate
59-30-3

folate

C30H36N8O5

C30H36N8O5

Conditions
ConditionsYield
Stage #1: folate With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide for 1h; Inert atmosphere; Darkness;
Stage #2: adamantylmethylamine With triethylamine In dimethyl sulfoxide for 48h; Inert atmosphere; Darkness;
86%

59-30-3Relevant articles and documents

-

Uyeo et al.

, p. 5339 (1950)

-

Method for preparing folic acid by virtue of micro-channel reaction (by machine translation)

-

Paragraph 0058-0060, (2020/12/14)

The invention belongs to the technical field of chemical synthesis of drugs, and relates to a synthesis method for preparing folic acid through a microchannel reactor. An intermediate 6 is prepared from cyanoethyl acetate as a raw material by one-step continuous operation, and the folic acid bulk drug is prepared through one-step reaction of the intermediate 6 and L - glutamate. The synthesis method uses the microchannel reactor to prepare the folic acid intermediate 2,triamino -4 - hydroxypyrimidine and folic acid, is safe and environment-friendly, and ensures the tasteless system. The method guarantees that the operation is simple and feasible, the solvent consumption is greatly reduced, 2,triamino -4 - hydroxyl pyrimidine yield and purity are obviously improved. (by machine translation)

Preparation method of 2,4,5-triamino-6-hydroxypyrimidine sulfate and folic acid

-

Paragraph 0098-0121, (2019/04/10)

The invention relates to a preparation method of 2,4,5-triamino-6-hydroxypyrimidine sulfate and folic acid. The preparation method comprises the following steps: enabling cyanoacetate and sodium nitrite to be subjected to reaction under the action of an organic solvent and/or an inorganic solvent and an acidic substance to obtain 2-oximidocyanoacetate; then, enabling the 2-oximidocyanoacetate andguanidine hydrochloride to be subjected to reaction under an alkaline condition to obtain 2,4-diamino-5-isonitroso-6-oxopyrimidine; enabling the 2,4-diamino-5-isonitroso-6-oxopyrimidine and hydrogen gas to be subjected to reaction under an alkaline condition by means of action of Pd/C to obtain 2,4,5-triamino-6-hydroxypyrimidine, and adding sulfuric acid to adjust the pH value to obtain 2,4,5-triamino-6-hydroxypyrimidine sulfate; and then, adding trichloroacetone and N-(4-aminobenzoyl)-L-glutamic acid to be subjected to reaction in a buffer solution under the action of a catalyst molecular sieve so as to obtain the folic acid. Based on the process route, the invention explores the influences of different reaction steps and refining conditions on the preparation route of 2,4,5-triamino-6-hydroxypyrimidine sulfate and the folic acid so as to reduce the wastewater pollution while increasing the yield.

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