Misplaced Pages

Pinitol

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 07:24, 23 October 2011 (Updating {{chembox}} (changes to verified fields - updated 'DrugBank_Ref', 'UNII_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs)). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 07:24, 23 October 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (changes to verified fields - updated 'DrugBank_Ref', 'UNII_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs))(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Pinitol
Chemical structure of pinitol
Chemical structure of D-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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
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/s1Key: DSCFFEYYQKSRSV-KLJZZCKASA-N
SMILES
  • COC1C(C(C(C(C1O)O)O)O)O
Properties
Chemical formula C7H14O6
Molar mass 194.18 g/mol
Melting point 179-185 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

Glycosides

Ciceritol is a pinitol digalactoside that can be isolated form seeds of chickpea, lentil and white lupin.

A cyclitol derivative can be found in the marine sponge Petrosia sp.

References

  1. Narayanan, 1987
  2. Introduction Sutherlandia frutescens - Kankerbossie
  3. Identification of the origin of commercial enological tannins by the analysis of monosaccharides and polyalcohols. M. Luz Sanz, Isabel Martínez-Castro and M. Victoria Moreno-Arribas, Food Chemistry, Volume 111, Issue 3, 1 December 2008, Pages 778-783, doi:10.1016/j.foodchem.2008.04.050
  4. Microbial oxidation in synthesis: A six step perparation of (+/-)-pinitol from benzene, S. V. Ley et al., Tetrahedron Lett. Volume 28, 1987, Pages 225 doi:10.1016/S0040-4039(00)95692-2
  5. Ciceritol, a pinitol digalactoside form seeds of chickpea, lentil and white lupin; Phytochemistry, Volume 22, Issue 8, 1983, Pages 1745-1751
  6. 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
Stub icon

This chemistry-related article is a stub. You can help Misplaced Pages by expanding it.

Categories:
Pinitol Add topic