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
59-30-3Relevant 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)
Heteropolyacid catalyzed safe and green folic acid synthesis method
-
Paragraph 0032; 0056; 0067-0075, (2019/10/01)
The invention belongs to the technical field of pharmaceutical chemistry synthesis, and relates to a heteropolyacid catalyzed safe and green folic acid synthesis method. The folic acid synthesis method comprises the following steps that (1), acrolein, heteropoly acid, 2,5,6-triamino-4-hydroxypyrimidine, p-aminobenzoate and alcoholic solvents are added into a reactor, stirring and warming are conducted, a reaction is conducted, material cooling is conducted after the reaction is finished, filtration is conducted, a filter cake is washed with the solvents, filtrate and washing liquid are combined, activated carbon is used for decoloration, the solvents are dried through distillation after extraction filtration is conducted, and a yellowish solid intermediate 6 is obtained; (2), sodium hydrogen glutamate and the intermediate 6 are dissolved into an alcohol-water mixed solution, stirring and a temperature reaction are conducted, after the reaction is finished, material cooling and coolingare conducted, heat preservation and crystallization are conducted, extraction filtration is conducted, the filter cake is washed with water, a crude folic acid product is obtained, and folic acid isobtained through refining. According to the synthesis method, acrolein which is low in price and easy to obtain is used as a raw material, the reaction is complete and rapid, no residue exists, it isguaranteed that the system is tasteless, and the yield and purity are obviously increased.