Pinitol

Pinitol
Names
IUPAC name
1D-chiro-Inositol
Systematic IUPAC name
(1R,2S,3R,4S,5S,6S)-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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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 Y
    Key: DSCFFEYYQKSRSV-KLJZZCKASA-N Y
  • CO[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O
Properties
C7H14O6
Molar mass 194.183 g·mol−1
Melting point 179 to 185 °C (354 to 365 °F; 452 to 458 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Pinitol is a cyclitol, a cyclic polyol. It is a known anti-diabetic agent isolated from Sutherlandia frutescens leaves. Gall plant tannins can be differentiated by their content of pinitol. It was first identified in the sugar pine (Pinus lambertiana). It is also found in other plants, such as in the pods of the carob tree.

Certain variants of the bacteria Pseudomonas putida have been used in organic synthesis, the first example being the oxidation of benzene, employed by Steven Ley in the synthesis of (±)-pinitol.