10361. Pinitol

Nomenclature

CAS number: 10284-63-6; 484-68-4 (dl-Form)
3-O-Methyl-d-chiro-inositol; d-pinitol; pinite; Inzitol (Humanetics).
C7H14O6; mol wt 194.18.
C 43.30%, H 7.27%, O 49.44%.

Description and references

Naturally occurring cyclitol discovered in sugar pine, Pinus lambertiana Dougl., Pinaceae; subsequently found in other conifers, soybean and other legumes, and the medicinal plants, sutherlandia and bougainvillea. Isoln from sugar pine: M. Berthelot, C. R. Acad. Sci. 41, 392 (1855); H. W. Wiley, J. Am. Chem. Soc. 13, 228 (1891) DOI; E. G. Griffin, J. M. Nelson, ibid. 37, 1552 (1915) DOI. Large scale prodn from pine stump wood: A. B. Anderson, Ind. Eng. Chem. 45, 593 (1953) DOI. Isoln from soybean: D. V. Phillips et al., J. Agric. Food Chem. 30, 456 (1982) DOI PubMed. Structure: A. B. Anderson et al., J. Am. Chem. Soc. 74, 1479 (1952) DOI. Total synthesis: S. V. Ley et al., Tetrahedron Lett. 28, 225 (1987) DOI; J. L. Acea et al., Tetrahedron: Asymmetry 7, 3535 (1996) DOI. Determn in plant extracts by 13C-NMR spectroscopy: E. Duquesnoy et al., Carbohydr. Res. 343, 893 (2008) DOI PubMed. Exptl insulin-like activity: S. H. Bates et al., Br. J. Pharmacol. 130, 1944 (2000) DOI PubMed. Clinical effect on blood glucose in diabetic patients: M.-J. Kang et al., J. Med. Food 9, 182 (2006) DOI PubMed.

Chemical structure

Properties

Small white prisms from methanol, mp 186°. [α]D22 +66.1° (c = 1 in water). Insol in abs alcohol, ether.

Use

Dietary supplement.