Pinitol

Pinitol
IUPAC name (1S,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
Other names 3-O-Methyl-D-chiro-inositol D-(+)-chiro-Inositol D-Pinitol Inzitol D-(+)-Pinitol (+)-Pinitol Sennitol Pinnitol (+/-)pinitol
Identifiers
CAS number	10284-63-6 Y=
PubChem	164619
ChemSpider	10369209 N
ChEBI	CHEBI:28548 N
ChEMBL	CHEMBL493737 N
Jmol-3D images	Image 1
SMILES COC1C(C(C(C(C1O)O)O)O)O
InChI InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5-,6+,7+/m0/s1 N Key: DSCFFEYYQKSRSV-KLJZZCKASA-N N
Properties
Molecular formula	C7H14O6
Molar mass	194.18 g/mol
Exact mass	194.079038 u
Melting point	179-185 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pinitol is a cyclitol, a cyclic polyol. It is a known anti-diabetic agent isolated from Sutherlandia frutescens leaves^[1][2]. Gall plant tannins can be differentiated by their content of pinitol^[3].

Certain variants of the bacteria Pseudomonas putida have been used in organic synthesis, the first example being the oxidation of benzene, employed by Prof. S. V. Ley in the synthesis of (+/-)pinitol.^[4]

Glycosides

Ciceritol is a pinitol digalactoside that can be isolated form seeds of chickpea, lentil and white lupin^[5].

A cyclitol derivative can be found in the marine sponge Petrosia sp^[6].

References

1. ^ Narayanan, 1987
2. ^ Introduction Sutherlandia frutescens - Kankerbossie
3. ^ Identification of the origin of commercial enological tannins by the analysis of monosaccharides and polyalcohols. M. Luz Sanz, Isabel Martínez-Castro and M. Victoria Moreno-Arribas, Food Chemistry, Volume 111, Issue 3, 1 December 2008, Pages 778-783, doi:10.1016/j.foodchem.2008.04.050
4. ^ Microbial oxidation in synthesis: A six step perparation of (+/-)-pinitol from benzene, S. V. Ley et al., Tetrahedron Lett. Volume 28, 1987, Pages 225 doi:10.1016/S0040-4039(00)95692-2
5. ^ Ciceritol, a pinitol digalactoside form seeds of chickpea, lentil and white lupin; Phytochemistry, Volume 22, Issue 8, 1983, Pages 1745-1751
6. ^ A cyclitol derivative as a replication inhibitor from the marine sponge Petrosia sp. Kim D.-K.; Young Ja Lim; Jung Sun Kim; Jong Hee Park; Nam Deuk Kim; Kwang Sik Im; Jongki Hong; Jung J. H. Journal of natural products, 1999, vol. 62, no5, pp. 773-776

• Pinitol on Sigma Aldrich website