4978. Inositol

Nomenclature

CAS number: 87-89-8
myo-Inositol; meso-inositol; i-inositol; hexahydroxycyclohexane; cyclohexanehexol; cyclohexitol; meat sugar; inosite; mesoinosite; phaseomannite; dambose; nucite; bios I; rat antispectacled eye factor; mouse antialopecia factor.
C6H12O6; mol wt 180.16.
C 40.00%, H 6.71%, O 53.28%.

Description and 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.

Chemical structure

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.

Derivative

Dihydrate.

Properties

Efflorescent crystals from water below 50°. d 1.524. mp 218°. Becomes anhydr at 100°.

Derivative

Monophosphate.

Nomenclature

CAS number: 573-35-3
C6H13O9P; mol wt 260.14.
C 27.70%, H 5.04%, O 55.35%, P 11.91%.

Description and 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.

Therapeutic Category

Vitamin B complex; lipotropic.

Keywords

Lipotropic; Vitamin/Vitamin Source