Folic Acid

Title: Folic Acid
CAS Registry Number: 59-30-3
CAS Name: N-[4-[[(2-Amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid
Additional Names: N-[p-[[(2-amino-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]glutamic acid; pteroylglutamic acid; N-(p-[(2-amino-4-hydroxypyrimido[4,5-b]pyrazin-6-yl)methylamino]benzoyl)glutamic acid; PGA; liver Lactobacillus casei factor; vitamin Bc; vitamin M; folsäure
Trademarks: Folacin; Foldine (Specia); Foliamin; Folicet (Mission Pharmacal); Folipac; Folettes (Fawns & McAllan); Folsan (Kali-Chemie); Folvite (Lederle); Incafolic; Millafol (Parke-Davis)
Molecular Formula: C19H19N7O6
Molecular Weight: 441.40
Percent Composition: C 51.70%, H 4.34%, N 22.21%, O 21.75%
Literature References: Hematopoietic vitamin present, free or combined with one or more additional molecules of L(+)-glutamic acid, in liver, kidney, mushrooms, spinach, yeast, green leaves, grasses: Mitchell et al., J. Am. Chem. Soc. 63, 2284 (1941). Isoln: Pfiffner et al., ibid. 69, 1476 (1947); Stokstad et al., ibid. 70, 3 (1948). Structure: Mowat et al., ibid. 14. Crystal structure: D. Mastropaolo et al., Science 210, 334 (1980). History of the different folic acid factors: Ann. N.Y. Acad. Sci. 48, 255-350 (1946). See also reviews by Subbarow et al. in Vitam. Horm. 3, 237-296 (1945); Pfiffner, Hogan, ibid. 4, 1-13 (1946). Several syntheses, see reviews by Gates, Chem. Rev. 41, 63-95 (1947); Hutchings, Mowat, Vitam. Horm. 6, 1-25 (1948); Sletzinger et al., J. Am. Chem. Soc. 77, 6365 (1955); US 2786056; US 2816109; US 2821527; US 2821528 (all 1958 to Merck & Co.); Sadao Kawanishi, US 2956057 (1960 to Kongo Kagaku Kabushiki Kaisha). Alternate syntheses: Bieri, Viscontini, Helv. Chim. Acta 56, 2905 (1973); E. Khalifa et al., ibid. 59, 242 (1976). Comprehensive reviews: Jaenicki, Kutzbach, Fortschr. Chem. Org. Naturst. 21, 183-274 (1963); Marchetti, Acta Vitaminol. Enzymol. 25, 41-64 (1971); F. J. Al-Shammary et al., Anal. Profiles Drug Subs. 19, 221-259 (1990). Review of role in prevention of neural tube defects: G. J. Locksmith, P. Duff, Obstet. Gynecol. 91, 1027-1034 (1998).
Properties: Yellowish-orange crystals. Extremely thin platelets (elongated at two ends) from hot water, no mp. Darkens and chars from about 250°. [a]D25 +23° (c = 0.5 in 0.1N NaOH). uv max (pH 13): 256, 283, 368 nm (log e 4.43, 4.40, 3.96). Very slightly sol in cold water (0.0016 mg/ml at 25°), sol to about 1% in boiling water. Slightly sol in methanol, appreciably less sol in ethanol and butanol. Insol in acetone, chloroform, ether, benzene. Relatively sol in acetic acid, phenol, pyridine, solns of alkali hydroxides and carbonates. Sol in hot dil HCl and H2SO4. Injectable solns are prepd by dissolving folic acid in normal sodium bicarbonate soln (which should be sterilized by filtration) or by preparing solns of the sodium or methylglucamine salt. A suspension of 1 g folic acid in 10 ml water has a pH of 4.0-4.8. Aq solns prepd with sodium bicarbonate have a pH between 6.5 and 6.8.
Optical Rotation: [a]D25 +23° (c = 0.5 in 0.1N NaOH)
Absorption maximum: uv max (pH 13): 256, 283, 368 nm (log e 4.43, 4.40, 3.96)
Therap-Cat: Vitamin (hematopoietic).
Therap-Cat-Vet: Nutritional factor (dietary requirement in poultry).
Keywords: Vitamin/Vitamin Source.
Folinic Acid Follicle-Stimulating Hormone Folpet Fomecins Fomepizole

Folic acid
Skeletal formula
Ball-and-stick model
Space-filling model
Folic acid as an orange powder
Identifiers
CAS number 59-30-3 YesY
PubChem 6037
ChemSpider 5815 YesY
UNII 935E97BOY8 YesY
DrugBank DB00158
KEGG C00504 N
ChEBI CHEBI:27470 YesY
ChEMBL CHEMBL1622 YesY
RTECS number LP5425000
ATC code B03BB01
Jmol-3D images Image 1
Properties
Molecular formula C19H19N7O6
Molar mass 441.40 g mol−1
Appearance yellow-orange crystalline powder
Melting point 250 °C (523 K) (decomposition) [1]
Solubility in water 1.6 mg/L (25 °C)[1]
log P -2.5
Acidity (pKa) 1st: 4.65, 2nd: 6.75, 3rd: 9.00[2]
Hazards
NFPA 704
NFPA 704.svg
0
1
0
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Folic acid (also known as vitamin M, vitamin B9,[3] vitamin Bc[4] (or folacin), pteroyl-L-glutamic acid, and pteroyl-L-glutamate)[dubious ] is a form of the water-soluble vitamin B9.[citation needed] Folate is a naturally occurring form of the vitamin, found in food, while folic acid is synthetically produced, and used in fortified foods and supplements.[5] Folic acid is itself not biologically active, but its biological importance is due to tetrahydrofolate and other derivatives after its conversion to dihydrofolic acid in the liver.[6]

Vitamin B9 (folic acid and folate) is essential for numerous bodily functions. Humans cannot synthesize folate de novo; therefore, folate has to be supplied through the diet to meet their daily requirements. The human body needs folate to synthesize DNA, repair DNA, and methylate DNA as well as to act as a cofactor in certain biological reactions.[7] It is especially important in aiding rapid cell division and growth, such as in infancy and pregnancy. Children and adults both require folic acid to produce healthy red blood cells and prevent anemia.[8]

Folate and folic acid derive their names from the Latin word folium, which means "leaf". Folate occurs naturally in many foods, and among plants are especially plentiful in dark green leafy vegetables.[9]

A lack of dietary folates can lead to folate deficiency. A complete lack of dietary folate takes months before deficiency develops as normal individuals have about 500–20,000 µg[10] of folate in body stores.[11] This deficiency can result in many health problems, the most notable one being neural tube defects in developing embryos. Common symptoms of folate deficiency include diarrhea, macrocytic anemia with weakness or shortness of breath, nerve damage with weakness and limb numbness (peripheral neuropathy),[12] pregnancy complications, mental confusion, forgetfulness or other cognitive declines, mental depression, sore or swollen tongue, peptic or mouth ulcers, headaches, heart palpitations, irritability, and behavioral disorders. Low levels of folate can also lead to homocysteine accumulation.[7] DNA synthesis and repair are impaired and this could lead to cancer development.[7]