Pinitol
Chemical compound
From Wikipedia, the free encyclopedia
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] It was first identified in the sugar pine (Pinus lambertiana).[4] It is also found in other plants, such as in the pods of the carob tree.[5]
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| Names | |
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| 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) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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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.[6]
Glycosides
Ciceritol is a pinitol digalactoside that can be isolated from seeds of chickpea, lentil and white lupin.[7]
A cyclitol derivative can be found in the marine sponge Petrosia sp.[8]
Biosynthesis
D-pinitol is the most widely distributed inositol ether in plants.[9] In Angiosperms, D-pinitol has a relatively straight forward and short biosynthesis which proceeds via the Loewus pathway. The precursor to the biosynthesis pathway is glucose-6-phosphate, which is converted to D-ononitol (1-D-4-O-methyl-myo-inositol) via myo-inositol. Ononitol is epimerized to yield D-pinitol via a D-ononitol epimerase using NADPH as a cofactor.[10]
