(1S,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol

Pinitol
Chemical structure of 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
  • 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 checkY
    Key: DSCFFEYYQKSRSV-KLJZZCKASA-N checkY
  • CO[C@H]1[C@@H]([C@H]([C@H]([C@@H]([C@@H]1O)O)O)O)O
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

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]

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

External links[]