Pinitol

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]

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
Properties
C7H14O6
Molar mass 194.18 g/mol
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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Infobox references

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]

References
  1. Narayanan, 1987
  2. "Introduction Sutherlandia frutescens - Kankerbossie" (PDF). Archived from the original (PDF) on 2011-07-21. Retrieved 2010-07-23.
  3. 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.
  4. 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.
  5. Tetik, N., & Yüksel, E. (2014). Ultrasound-assisted extraction of d-pinitol from carob pods using response surface methodology. Ultrasonics sonochemistry, 21(2), 860-865.
  6. 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
  7. Quemener, Bernard; Brillouet, Jean-Marc (1983). "Ciceritol, a pinitol digalactoside form seeds of chickpea, lentil and white lupin". Phytochemistry. 22 (8): 1745–1751. doi:10.1016/S0031-9422(00)80263-0.
  8. 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
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