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Folic acid

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Folic acid Basic information
Folic acid Chemical Properties
  • Melting point:250 °C
  • alpha 20 º (c=1, 0.1N NaOH)
  • Boiling point:552.35°C (rough estimate)
  • Density 1.4704 (rough estimate)
  • refractive index 1.6800 (estimate)
  • storage temp. 2-8°C
  • solubility boiling water: soluble1%
  • pkapKa 2.5 (Uncertain)
  • form Crystalline Powder
  • color Yellow to orange
  • OdorOdorless
  • PH Range4
  • Water Solubility 1.6 mg/L (25 ºC)
  • Merck 14,4221
  • BRN 100781
  • Stability:Stable. Incompatible with heavy metal ions, strong oxidizing agents, strong reducing agents. Solutions may be light and heat sensitive.
  • InChIKeyOVBPIULPVIDEAO-LBPRGKRZSA-N
  • CAS DataBase Reference59-30-3(CAS DataBase Reference)
  • NIST Chemistry ReferenceFolic acid(59-30-3)
  • EPA Substance Registry SystemL-Glutamic acid, N-[4-[[(2-amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]- (59-30-3)
Safety Information
MSDS
Folic acid Usage And Synthesis
  • DescriptionFolic acid (folate) is a kind of B-vitamin which is mainly present in the liver and kidney. It has various kinds of pharmacological and physiological effects. It is involved in amino acid metabolism, purine and pyrimidine synthesis, and is also essential for hematopoiesis and red blood cell generation. In women pregnancy, folate can effectively prevent neural tube defects in the baby. It plays important role in fertility through contributing to spermatogenesis. It can also reduce the incidence of heart disease, stroke and cancer. 
    Folate deficiency may lead to various kinds of diseases including glossitis, diarrhea, depression, confusion, anemia, and fetal neural tube defectsand brain defects (during pregnancy). Other symptoms may include fatigue, gray hair, mouth sores, poor growth, and swollen tongue.
  • Chemical Propertiesorange to yellow crystalline powder
  • OriginatorFolvite, Lederle, US ,1946
  • OccurrenceSynthetic
  • Usesfolic acid is generally used as an emollient. In vitro and in vivo skin studies now indicate its capacity 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. Folic acid is a member of the vitamin B complex and is naturally occurring in leafy greens.
  • UsesLiterature tends to indicate that B vitamins cannot pass through the layers of the skin and, therefore, are of no value in the skin surface. Current experiments demonstrate, however, that vitamin B2 acts as a chemical reaction accelerator, enhancing the performance of tyrosine derivatives in suntan-accelerating preparations.
  • UsesFolic Acid is a water-soluble b-complex vitamin that aids in the for- mation of red blood cells, prevents certain anemias, and is essential in normal metabolism. high-temperature processing affects its sta- bility. it is best stored at lower than room temperatures. it is also termed folacin. it is found in liver, nuts, and green vegetables.
  • UsesA vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA, it also acts as a cofactor in biological reactions involving folate.
  • Useshematopoietic vitamin
  • DefinitionChEBI: An N-acyl-amino acid that is a form of the water-soluble vitamin B9. Its biologically active forms (tetrahydrofolate and others) are essential for nucleotide biosynthesis and homocysteine remethylation.
  • Manufacturing ProcessThe 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 FunctionTreatment of B vitamin (folacin) deficiency
  • General DescriptionOdorless orange-yellow needles or platelets. Darkens and chars from approximately 482°F.
  • Air & Water ReactionsInsoluble in water. Aqueous solutions have pHs of 4.0-4.8.
  • Reactivity ProfileAcid 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 HazardFlash point data for Folic acid are not available; however, Folic acid is probably combustible.
  • Safety ProfilePoison by intraperitoneal and intravenous routes. Experimental teratogenic effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
  • Veterinary Drugs and TreatmentsFolic 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.
  • Purification MethodsIf 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.]
Folic acid Preparation Products And Raw materials
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