Folic acid CAS 59-30-3
Introduction：Basic information about Folic acid CAS 59-30-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Folic acid Basic informationDescription
| Product Name: | Folic acid |
| Synonyms: | EZNA KIT FUNGAL DNA MINI;KIT BLOOD DNA EZNA 5 TESTS;PTEROYL-L-GLUTAMIC ACID;PTEROYLMONOGLUTAMIC ACID;PTEROYLGLUTAMIC ACID;PTEROYGLUTAMIC ACID;PTEGLU;PGA |
| CAS: | 59-30-3 |
| MF: | C19H19N7O6 |
| MW: | 441.4 |
| EINECS: | 200-419-0 |
| Product Categories: | Inhibitors;Nutritional Supplements;food or feed additives;Vitamin Ingredients;Food and Feed Additive;Biochemistry;Vitamins;raw material;FOLICET;vitamin;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Intermediates & Fine Chemicals;Pharmaceuticals;59-30-3 |
| Mol File: | 59-30-3.mol |
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) |
| bulk density | 110kg/m3 |
| refractive index | 1.6800 (estimate) |
| storage temp. | 2-8°C |
| solubility | boiling water: soluble1% |
| pka | pKa 2.5 (Uncertain) |
| form | Crystalline Powder |
| color | Yellow to orange |
| Odor | Odorless |
| PH Range | 4 |
| PH | 4.0-4.8 (25°C, 100g/L in H2O) |
| biological source | synthetic (organic) |
| Water Solubility | 1.6 mg/L (25 ºC) |
| Merck | 14,4221 |
| BRN | 100781 |
| BCS Class | 3 |
| Stability: | Stable. Incompatible with heavy metal ions, strong oxidizing agents, strong reducing agents. Solutions may be light and heat sensitive. |
| Cosmetics Ingredients Functions | SKIN CONDITIONING |
| InChIKey | OVBPIULPVIDEAO-LBPRGKRZSA-N |
| SMILES | NC(N1)=NC(C2=C1N=CC(CNC3=CC=C(C(N[C@@H](CCC(O)=O)C(O)=O)=O)C=C3)=N2)=O |
| LogP | -0.990 (est) |
| CAS DataBase Reference | 59-30-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Folic acid(59-30-3) |
| EPA Substance Registry System | L-Glutamic acid, N-[4-[[(2-amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]- (59-30-3) |
Safety Information
| Risk Statements | 33-62-68 |
| Safety Statements | 24/25 |
| WGK Germany | 1 |
| RTECS | LP5425000 |
| F | 8 |
| TSCA | TSCA listed |
| HS Code | 29362900 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 59-30-3(Hazardous Substances Data) |
| Toxicity | A water soluble vitaminrequired in the diet of mammals. Sulfonamide drugs are selectivelytoxic to bacteria because they inhibit the incorporationof p-aminobenzoic acid into folic acid, a biosynthetic processin bacteria. Folic acid deficiency adversely affects prenataldevelopment in humans. Dietary supplementation with folicacid dramatically reduces the incidence of neural tube defectsin humans. Folic acid deficiency may also contribute to the causes of megaloblastic macrocytic anemia and a consequenceof this is that this disease can be induced, as a side effect,when methotrexate, a folic acid antagonist, is used in cancerchemotherapy |
| Description | Folic acid (folate,59-30-3) 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. |
| Description | Folic acid is an essential B vitamin. It is converted to folate in vivo, which is a necessary cofactor for a variety of biological processes, including nucleotide synthesis and, thus, DNA synthesis and repair, among others. A deficiency in dietary folic acid can lead to a range of developmental and cognitive disorders, most prominently neural tube defects and congenital heart defects. |
| Description | In the 1930s, brewer’s yeast was found to prevent anemia. Folicacid was later discovered to be the nutrient responsible for thiseffect and was purified in 1941 by Mitchell and coworkers(Mitchell et al., 1941). Folate is needed for biosynthesis ofpurines and thymidine for DNA and RNA synthesis in all cells.It is also involved in metabolism of some of the amino acidsneeded for protein synthesis, especially the conversions ofserine to glycine and homocysteine to methionine. This makesthe nutrient especially important during periods of rapid celldivision, such as in pregnancy. Folate is also involved intransfer of one-carbon groups for methylation reactions. Therole of folate in cell division was capitalized upon in thesynthesis of aminopterin, a folate antagonist, which was one ofthe first anticancer drugs produced. |
| Chemical Properties | orange to yellow crystalline powder |
| Physical properties | The folates include a large number of chemically related species, each differing with respect to the various substituents possible at three sites on the pteroylglutamic acid basic structure. More than 170 different folates are theoretically possible. Not all of these occur in nature; but it has been estimated that as many as 100 different forms are found in animals. The folates from most natural sources usually have a single carbon unit at N-5 and/or N-10; these forms participate in the metabolism of the single-carbon pool. Folic acid (pteroylmonoglutamic acid) is an orange-yellow crystalline substance that is soluble in water but insoluble in ethanol or less polar organic solvents. It is unstable to light, to acidic or alkaline conditions, to reducing agents, and, except in dry form, to heat. It is reduced in vivo enzymatically (or in vitro with a reductant such as dithionite) first to 7,8-dihydrofolic acid (FH2) and then to FH4; both of these compounds are unstable in aerobic environments and must be protected by the pres ence of an antioxidant (e.g., ascorbic acid, 2-mer Two derivatives of folic acid, each having an amino group in the place of the hydroxyl at C-4, are folate antagonists of biomedical use: aminopterin (4-aminofolic acid) and methotrexate (4-amino-N10-methylfolic acid). Aminopterin is used as a rodenticide; methotrexate is an antineoplastic agent. |
| Originator | Folvite, Lederle, US ,1946 |
| Occurrence | Synthetic |
| Uses | Literature 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. |
| Uses | Folic 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. |
| Uses | A vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA, it also acts as a cofactor in biological reactions involving folate. |
| Uses | hematopoietic vitamin |
| Uses | folic 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. |
| Definition | ChEBI: Folic acid is 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. It has a role as a human metabolite, a nutrient and a mouse metabolite. It is a member of folic acids and a N-acyl-amino acid. It is functionally related to a pteroic acid. It is a conjugate acid of a folate(2-). |
| 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 and95 grams of bromine are added thereto in drops while being stirred and thestirring is continued for about 1 hour. The resulting reaction solution isdistilled 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 100grams of 1bromo-1,3,3-trichloroacetone, which is agitated and cooled. A whitescaly crystal of hydrate of 1-bromo-1,3,3-trichloroacetone is obtained (100grams), having a melting point of 52° to 53°C. 8.9 grams of 2,4,5-triamino-6-hydroxypyrimidine hydrochloride and 8 gramsof p-aminobenzoylglutamic acid are dissolved in 400 cc warm water, which iscooled at 35° to 27°C and adjusted to pH 4 by using 20% caustic sodasolution. To this solution was simultaneously added dropwise a solutionobtained by dissolving 13.4 grams of 1-bromo-1,3,3-trichloroacetone hydratein 90 cc of 50% methanol and 24 grams of 35% aqueous sodium bisulfitesolution over a period of approximately 2 hours. During this period, in orderto maintain the pH value of the reaction solution at 4 to 5, 20% caustic sodasolution is added from time to time. The precipitate, formed by stirring for 5hours after dropping was finished, is filtered, and the filtrated precipitate isrefined; 5.6 grams of pure pteroylglutamic acid is obtained. |
| Therapeutic Function | Treatment of B vitamin (folacin) deficiency |
| General Description | Odorless orange-yellow needles or platelets. Darkens and chars from approximately 482°F. |
| 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 anaemia Supplement 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, andhorses (theoretically in other animal species as well) often due tosmall intestinal disease. Cats with exocrine pancreatic insufficiencyappear to be most at risk for folate and cobalamin deficiencies secondaryto malabsorption of folic acid in the diet. Dogs with exocrinepancreatic insufficiency often are noted to have increased folate levelssecondary to overgrowths of folate-synthesizing bacteria in theproximal small intestine. Chronic administration of dihydrofolatereductase inhibiting drugs such as pyrimethamine, ormetoprim ortrimethoprim can potentially lead to reduced activated folic acid(tetrahydrofolic acid); folic acid supplementation is sometimes prescribedin an attempt to alleviate this situation. |
| Drug interactions | Potentially hazardous interactions with other drugs Antiepileptics: reduces phenytoin, primidone andphenobarbital levels. Cytotoxics: avoid with raltitrexed. |
| Metabolism | Folic acid given therapeutically enters the portalcirculation largely unchanged, since it is a poor substratefor reduction by dihydrofolate reductase. It is convertedto the metabolically active form 5-methyltetrahydrofolatein the plasma and liver. Folate undergoes enterohepaticcirculation. Folate metabolites are eliminated in the urineand folate in excess of body requirements is excretedunchanged 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.] |
| References | [1] Patent: CN106279174, 2017, A. Location in patent: Paragraph 0023; 0024; 0025; 0026; 0027; 0028; 0029-0031 |
Folic acid Preparation Products And Raw materials
| Raw materials | Sodium metabisulfite-->Basic Orange 2-->2,5,6-Triaminopyrimidin-4-ol sulphate-->3,5-DI-T-BUTYL-4-METHOXYBENZALDEHYDE-->P-AMINOBENZAMIDE GLUTAMIC ACID-->1,1,3-Trichloroacetone-->BUFFER SOLUTION(ACETIC ACID/SODIUM ACETATE)-->Sodium bisulfite-->p-Aminobenzoyl Glutamic Acid |
| Preparation Products | 5,10-DiforMyl-5,6,7,8-tetrahydro Folic Acid-->Aminopterin-->Pterin-6-carboxylic acid-->DL-Pyroglutamic acid-->L-Tetrahydrofolic Acid |
