Pinitol

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
CAS Number	10284-63-6 =;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28548 ;
ChEMBL	ChEMBL493737 ;
ChemSpider	10369209 ;
PubChem CID	164619;
UNII	TF9HZN9T0M ;
CompTox Dashboard (EPA)	DTXSID50883108 ;
	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 Key: DSCFFEYYQKSRSV-KLJZZCKASA-N ;
	SMILES CO[C@H]1[C@@H]([C@H]([C@H]([C@@H]([C@@H]1O)O)O)O)O;
Properties
Chemical formula	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

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]

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]

Narayanan, 1987
"Introduction Sutherlandia frutescens - Kankerbossie" (PDF). Archived from the original (PDF) on 2011-07-21. Retrieved 2010-07-23.
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.
Tetik, N., & Yüksel, E. (2014). Ultrasound-assisted extraction of d-pinitol from carob pods using response surface methodology. Ultrasonics sonochemistry, 21(2), 860-865.
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
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.
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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