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Folic acid ( CASNO:59-30-3 )

Identification and Related Records
Name:
Folic acid
CAS Registry number:
59-30-3
Synonyms:
4-Pteridinol, 2-amino-6-((p-((1, 3-dicarboxypropyl)carbamoyl)anilino)methyl)-
Acido folico [INN-Spanish]
Folsav
(2S)-2-[[4-[(2-amino-4-oxo-1H-pteridin-7-yl)methylamino]benzoyl]amino]pentanedioate
Vitamin M
Pteroyl-L-monoglutamic acid
Folvite
Folaemin [Netherlands]
L-Glutamic acid, N-(4-((2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-
Folico (Italy)
pteridinyl)methyl]amino]benzoyl]-
Kyselina listova [Czech]
Folettes
Folipac
Foliamin
(2R)-2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioate
Folasic (Australia)
Incafolic
L-Glutamic acid,N-[4-[[(2-amino-1,4- dihydro-4-oxo-6-pteridinyl)methyl]amino]- benzoyl]-
Glutamic acid, pteroyl-, L-
Folic acid (TN)
L-glutamic acid, N-[4-[[(2-amino-4,8-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-
Vitamin Be
(2S)-2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
Pteroylmonoglutamate
Glutamic acid, N-[p-[[(2-amino-4-hydroxypyrimido(4, 5-b)pyrazin-6-yl)methyl]amino]benzoyl]-, L
L-Glutamic acid, N-(4-(((2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-, K salt
Folate
Glutamic acid, N-(p-(((2-amino-4-hydroxy-6-pteridinyl)methyl)amino)benzoyl)-, L-
Folacin
Vitamin B9
EINECS(EC#):
200-419-0
Molecular Formula:
C19H19N7O6
Molecular Weight:
441.4
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)/t12-/m0/s1
Canonical SMILES:
C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)N=C(N3)N
Isomers smiles:
C1=CC(=CC=C1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)N=C(N3)N
Chemical and Physical Properties
Appearance:
Yellow to orange yellow crystals or crystalline powder.
Density:
1.68 g/cm3
Melting Point:
250℃
Alpha:
20° (C=1, 0.1N NAOH)
Water:
1.6 mg/L (25℃)
Solubilities:
Water Solubility, 1.6 mg/L (25°C)
Color/Form:
Yellowish-orange crystals; extremely thin platelets (elongated @ 2 ends) from hot water
Stability:
Stable. Incompatible with heavy metal ions, strong oxidizing agents, strong reducing agents. Solutions may be light and heat sensitive.
Storage temp:
2-8°C
Spectral properties:
Specific optical rotation: +23 deg at 25 deg C/D (c= 0.5 in 0.1 N sodium hyroxide)
UV max (pH 13): 256, 283, 368 nm (log E 4.43, 4.40, 3.96)
MASS: 76456 44 (NIST/EPA/MSDC Mass Specral Database 1990 Version)
IR: 5025 (Coblentz Society Spectral Collection)
UV: 2-601 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
Computed Properties:
Molecular Weight:441.39746 [g/mol]
Molecular Formula:C19H19N7O6
XLogP3-AA:-1.1
H-Bond Donor:6
H-Bond Acceptor:9
Rotatable Bond Count:9
Tautomer Count:60
Exact Mass:441.139681
MonoIsotopic Mass:441.139681
Topological Polar Surface Area:209
Heavy Atom Count:32
Formal Charge:0
Complexity:767
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:7
Feature 3D Donor Count:5
Feature 3D Anion Count:2
Feature 3D Cation Count:2
Feature 3D Ring Count:3
Effective Rotor Count:10
Conformer Sampling RMSD:1
CID Conformer Count:60
Safety and Handling
Hazard Codes:
Xn
Risk Statements:
R33;R62;R68
Safety Statements:
S24/25
Safety:
Risk Statements: 33-62-68
R33: Danger of cumulative effects.
R62: Risk of impaired fertility.
R68: Possible risk of irreversible effects.
Safety Statements: 24/25
S24/25: Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: LP5425000
F: 8
Formulations/Preparations:
5 mg (base) per mL (Rx) [Folvite (benzyl alcohol 1.5 %)]; 10 mg per mL (Rx)
Folic acid (FOLVITE) is marketed as oral tablets containing 0.4, 0.8, and 1 mg and as an aqueous solution for injection. Tablets of folic acid contain either 0.1, 0.4, 0.8, or 1 mg of pteroylglutamic acid, as an aqueous solution for injection, and in combination with other vitamins and minerals
Injectable solutions are prepared by dissolving folic acid in normal sodium bicarbonate solution (which should be sterilized by filtration) or by preparing solutions of the sodium or methylglucamine salt.
Lexpec Folic Acid. Syrup containing folic acid 2.5 mg in each 5 mL (recommended diluent, Sorbitol Solution or Sorbitol Solution and water, equal parts).
10% feed grade, USP
Exposure Standards and Regulations:
Folic acid (CAS Reg. No. 59-30-3), also known as folacin or folate, may be safely used in food as a nutrient in accordance with the following prescribed conditions: (a) Folic acid is the chemical N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid. (b) Folic acid meets the specifications of the Food Chemicals Codex, 4th ed. (1996), pp. 157?158, which is incorporated by reference in accordance with 5 U.S.C. 552(a) and 1 CFR part 51. (c) Folic acid may be added to foods subject to a standard of identity established under section 401 of the Federal Food, Drug, and Cosmetic Act (the act) when the standard of identity specifically provides for the addition of folic acid. (d) Folic acid may be added, at levels not to exceed 400 micrograms (g) per serving, to breakfast cereals, as defined under 170.3(n)(4) of this chapter, and to corn grits at a level such that each pound of corn grits contains not more than 1.0 milligram of folic acid. (e) Folic acid may be added to infant formula in accordance with section 412(i)(1) of the act or with regulations issued under section 412(i)(2) of the act which are codified in ?107.100 of this chapter. (f) Folic acid may be added to a medical food, as defined in section 5(b)(3) of the Orphan Drug Act (21 U.S.C. 360ee(b)(3)), at levels not to exceed the amount necessary to meet the distinctive nutritional requirements of the disease or condition for which the food is formulated. (g) Folic acid may be added to food for special dietary use at levels not to exceed the amount necessary to meet the special dietary needs for which the food is formulated. (h) Folic acid may be added to foods represented as meal-replacement products, in amounts not to exceed: (1) Four hundred per serving if the food is a meal-replacement that is represented for use once per day; or (2) Two hundred per serving if the food is a meal-replacement that is represented for use more than once per day.
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Folic acid is included in weight control drug products.
Reactivities and Incompatibilities:
Folic acid is incompatible with oxidizing and reducing agents and with heavy metal ions.
Specification:
Folic acid , with CAS number of 59-30-3, can be called Pteroyl-l-glutamic acid ; pteroylmonoglutamic acid ; pteroylglutamic acid ; pteroyglutamic acid ; pteglu ; pga ; n-[4-[[(2-amino-4-hydroxy-6-pteridyl)methyl]amino]benzoyl]glutamic acid ; n-4-[(2-amido-4-oxo-1,4-dihydro-6-terene)methylamino]benzoyl-l-glutamic acid . Folic Acid (CAS NO.59-30-3) is a toxic substance, with flammability, burning will produce toxic gases, so it should be stored in a tightly closed container which is cool, dry and well-ventilated, be away from incompatible substances and light. Dry powder, foam, sand, carbon dioxide, water mist can be used if something urgent happened.
Octanol/Water Partition Coefficient:
log Kow = -2.81 /Estimated/
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing
Condensation of 2,5,6-triamino-4(3H)-pyrimidinone, p-aminobenzoyl-L-glutamic acid, and 2,3-dibromopropanal.
Synthetic pteroylglutamic acid is made by the reaction of 2,3-di-bromopropanol,2,4,5-triamino-6-hydroxypyrimidine and para-aminobenzoyl glutamic acid

U.S. Imports
(1983) 5.07X10+7 g
Usage:
Medication.
Biomedical Effects and Toxicity
Pharmacological Action:
- Agents which improve the quality of the blood, increasing the hemoglobin level and the number of erythrocytes. They are used in the treatment of anemias.
- A group of water-soluble vitamins, some of which are COENZYMES.
Therapeutic Uses:
Hematinics
Folic acid is indicated for prevention and treatment of folic acid deficiency states , including megaloblastic anemia and anemias of nutritional origin, pregnancy, infancy, or childhood.
Recommended intakes may be increased and /or supplementation may be necessary in the following persons or conditions (based on documented folic acid deficiency): Alcoholism, hemolytic anemia, chronic fever, gastrectomy, chronic hemodialysis, infants (low birth weight, breast-fed, or those receiving unfortified formulas such as evaporated milk or goats milk), Intestinal disease (celiac disease, tropical sprue, persistent diarrhea), malabsorption syndromes associated with hepatic-biliary disease (hepatic function impairment, alcoholism with cirrhosis), /and/ prolonged stress.
MEDICATION (VET): To prevent macrocytic anemia, embryonic death, cervical paralysis, and perosis In chicks.
MEDICATION (VET): Nutritional factor (dietary requirement in poultry).
Folic acid is indicated for the prevention of some birth defects and appears, as well, to confer significant protection against cardiovascular disease and some forms of cancer.
Several studies have shown that women with low plasma folate and vitamin B12 concentrations are at significantly increased risk of giving birth to babies with neural tube defects, as well as some other birth defects. Moreover, several double-blind, placebo controlled studies have demonstrated that neural tube defects can be significantly prevented when women take folic acid supplements during the periconceptional period. A dose of 400 micrograms is now widely recommended for women of reproductive age.
Biomedical Effects and Toxicity:
Folic acid is absorbed rapidly from the GI tract following oral administration oral administration; the vitamin is absorbed mainly in the proximal portion of the small intestine.
The monoglutamate forms of folate, including folic acid, are transported across the proximal small intestine via a saturable pH-dependent process. Higher doses of the pteroylmonoglutamates, including folic acid, are absorbed via a nonsaturable passive diffusion process. The efficiency of absorption of the pteroylmonoglutamates is greater than that of pteroylpolyglutamates.
Following oral administration, peak folate activity in blood occurs within 30 to 60 minutes. Synthetic folate is almost 100% bioavailable when administered in fasting individuals. While the bioavailability of naturally occurring folate in food is about 50%, bioavailability of synthetic folic acid consumed with a meal ranges from 85 to 100%.
Approximately two-thirds of folate in plasma is protein bound. When pharmacologic doses of folic acid are administered, a significant amount of unchanged folic acid is found in the plasma. The liver contains more than 50% of the body stores of folate, or about 6 to 14 milligrams. The total body store of folate is about 12 to 28 miligrams.
Tetrahydrofolic acid and its derivatives are distributed to all body tissues; the liver contains about one-half of total body folate stores. Folate is actively concentrated in the CSF, and normal CSF folate are reported to be about 0.0016 to 0.021 ug/mL. Normal red cell folate concentrations range from 0.175 to 0.316 ug/mL.
When 1 ug of tritium-labeled folic acid/kg body wt is injected iv into a normal man, 60% is removed In 1 circulation time & 90-95% is removed in 3 min, suggesting that there is a high tissue affinity For "physiological" quantities of folic acid.
Folic acid is distributed into milk.
Following oral administration of single 0.1 to 0.2 mg doses of folic acid in healthy adults, only a trace amount of the drug appears in the urine. Following administration of large doses, the renal tubular reabsorption maximum is exceeded, and excess folate is excreted unchanged in urine. After doses of about 2.5 to 5.0 mg, about 50% of a dose is excreted in urine and after a 15 mg dose, up to 90% may be recovered in the urine.
Small amounts of of orally administered folic acid have been recovered from feces. About 0.05 mg per day of normal folate body stores is lost by a combination of urinary and fecal excretion and oxidative cleavage of the molecule.
Folate is excreted in the urine as folate cleavage products. Intact folate enters the glomerulus and is reabsorbed into the proximal renal tubule. Very little intact folate is excreted in the urine. Folate is excreted in the bile and much of it is reabsorbed via the enterohepatic circulation.
Folic acid is removed by hemodialysis.
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,400(SRC), determined from a water solubility of 1.6 mg/L(2) and a regression-derived equation(3), indicates that folic acid is expected to have slight mobility in soil(SRC). The estimated pKa values of the two carboxylic acid moieties of folic acid are 3.5 and 4.3(4) indicating that this compound will primarily exist as an anion in the environment(5). Volatilization of folic acid from moist soil surfaces is not an important fate process(SRC) because anions do not volatilize. Folic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.2X10-20 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation is not expected to be an important environmental fate process in soil as indicated by a low BOD/COD ratio obtained using a sewage inoculum test(7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,400(SRC), determined from a water solubility of 1.6 mg/L(2) and a regression-derived equation(3), indicates that folic acid is expected to adsorb to suspended solids and sediment(SRC). The estimated pKa values of the carboxylic acid moieties of folic acid are 3.5 and 4.3(3), indicating that this compound will primarily exist in anion form in the environment(4). Volatilization from water surfaces does not occur since anions do not volatilize. According to a classification scheme(5), an estimated BCF of 3.2(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegadation is not expected to be an important environmental fate process in water as indicated by a low BOD/COD ratio obtained using a sewage inoculum test(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), folic acid, which has an estimated vapor pressure of 6.2X10-10 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase folic acid may be removed from the air by wet and dry deposition(SRC). Folic acid absorbs UV light >290 nm(3); therefore folic acid may be susceptible to photolysis although the rate is not known.
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