Pinitol
 | |
| Names | |
|---|---|
| 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 | |
10284-63-6  = | |
| ChEBI | CHEBI:28548  |
| ChEMBL | ChEMBL493737 |
| ChemSpider | 10369209 |
| |
| Jmol-3D images | Image |
| PubChem | 164619 |
| |
| Properties | |
| C7H14O6 | |
| Molar mass | 194.18 g/mol |
| Melting point | 179 to 185 °C (354 to 365 °F; 452 to 458 K) |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| 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] It was first identified in the sugar pine (Pinus lambertiana).[4]
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.[5]
Glycosides
Ciceritol is a pinitol digalactoside that can be isolated from seeds of chickpea, lentil and white lupin.[6]
A cyclitol derivative can be found in the marine sponge Petrosia sp.[7]
References
- ↑ Narayanan, 1987
- ↑ Introduction Sutherlandia frutescens - Kankerbossie
- ↑ Sanz, M. L.; Martínez-Castro, I.; Moreno-Arribas, M. V. (2008). "Identification of the origin of commercial enological tannins by the analysis of monosaccharides and polyalcohols". Food Chemistry 111 (3): 778. doi:10.1016/j.foodchem.2008.04.050.
- ↑ Anderson, A. B.; MacDonald, D. L.; Fischer, H. O. L. (1952). "The Structure of Pinitol". Journal of the American Chemical Society 74 (6): 1479. doi:10.1021/ja01126a036.
- ↑ Microbial oxidation in synthesis: A six step preparation of (+/-)-pinitol from benzene, S. V. Ley et al., Tetrahedron Lett. Volume 28, 1987, Pages 225 doi:10.1016/S0040-4039(00)95692-2
- ↑ Ciceritol, a pinitol digalactoside from seeds of chickpea, lentil and white lupin; Phytochemistry, Volume 22, Issue 8, 1983, Pages 1745-1751
- ↑ 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