CAS No 87-89-8 , cyclohexane-1,2,3,4,5,6-hexol

Title: Inositol
CAS Registry Number: 87-89-8
CAS Name: myo-Inositol
Synonyms: meso-inositol; i-inositol; hexahydroxycyclohexane; cyclohexanehexol; cyclohexitol; meat sugar; inosite; mesoinosite; phaseomannite; dambose; nucite; bios I; rat antispectacled eye factor; mouse antialopecia factor
Molecular Formula: C6H12O6
Molecular Weight: 180.16
Percent Composition: C 40.00%, H 6.71%, O 53.28%
Literature References: Widely distributed in plants and animals. Growth factor for animals and microorganisms. Isoln from heart muscle: Scherer, Ann. 73, 322 (1850); from liver: Woolley, J. Biol. Chem. 139, 29 (1941). Synthesis: Wieland, Wishart, Ber. 47, 2082 (1914); Anderson, Wallis, J. Am. Chem. Soc. 70, 2931 (1948). Obtained commercially from corn steep liquor, since inositol is present as phytic acid in corn: Bartow, Walker, Ind. Eng. Chem. 30, 300 (1938); US 2112553 (1938); Hoglan, Bartow, J. Am. Chem. Soc. 62, 2397 (1940); Elkin, Meadows, US 2414365 (1947); GB 601273 (1948 to Corn Prod. Refining). Nine possible stereoisomers: Seven are optically inactive or meso. Two optically active forms, the racemic form, and several cis,trans-isomers occur naturally. The prevalent natural form is cis-1,2,3,5-trans-4,6-cyclohexanehexol which is described here. Reviews: R. Beckmann, m-Inosit (Editio Cantor, Aulendorf, 1953); several authors in The Vitamins vol. 2,, W. H. Sebrell, Jr., R. S. Harris, Eds. (Academic Press, New York, 1954) pp 321-386; ibid. vol. 3 (2nd ed., 1971) pp 340-415.
Properties: Anhydr, non-hygroscopic crystals from water or acetic acid above 80°. Sweet taste. d 1.752. mp 225-227°. Optically inactive. Soly in water at 25°: 14 g/100 ml soln; at 60°: 28 g/100 ml soln. Slightly sol in alc. Practically insol in ether and other common organic solvents. Aq solns are neutral to litmus.
Melting point: mp 225-227°
Density: d 1.752
 
Derivative Type: Dihydrate
Properties: Efflorescent crystals from water below 50°. d 1.524. mp 218°. Becomes anhydr at 100°.
Melting point: mp 218°
Density: d 1.524
 
Derivative Type: Monophosphate
CAS Registry Number: 573-35-3
Molecular Formula: C6H13O9P
Molecular Weight: 260.14
Percent Composition: C 27.70%, H 5.04%, O 55.35%, P 11.91%
Literature References: Prepn: Posternak, Posternak, Helv. Chim. Acta 12, 1165 (1929); McCormick, Carter, Biochem. Prep. 2, 65 (1952).
Properties: Crystals from water + alcohol, dec 195-197°. Titrates as a dibasic acid. Freely soluble in water (1 g dissolves in 3 ml H2O). Practically insol in abs ethanol, ether. Remarkably resistant to hydrolysis by boiling with strong alkali. May be hydrolyzed by boiling with 6N HCl for 14 hrs.
 
Therap-Cat: Vitamin B complex; lipotropic.
Keywords: Lipotropic; Vitamin/Vitamin Source.