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.

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