441252
D-Pinitol
95%
Synonym(s):
3-O-Methyl-D-chiro-inositol
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About This Item
Empirical Formula (Hill Notation):
C7H14O6
CAS Number:
Molecular Weight:
194.18
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
95%
form
powder
optical activity
[α]20/D 60.0 to 70.0°, c = 1% in H2O
mp
179-185 °C (lit.)
SMILES string
CO[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O
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
InChI key
DSCFFEYYQKSRSV-KLJZZCKASA-N
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General description
D-pinitol, commonly found conifers, is an isomer of L-quebrachitol.
Application
D-pinitol may be used as a starting material to prepare its azole nucleoside analogs. It may also be used in the preparation of 1D-1,5-dideoxy-1,5-difluoro-neo-inositol and 1D-1-deoxy-1-fluoro-myo-inositol.
Precursor to biologically active fluorinated isosteres of inositol, which show cell growth inhibitory properties. Has shown antidiabetic properties in mice. Believed to be a salt stress regulator in a wide range of plants.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Narayanan, C.R. et al.
Current Science, 56, 139-139 (1987)
Efficient synthetic routes to fluorinated isosteres of inositol and their effects on cellular growth.
Kozikowski AP, et al.
Journal of the American Chemical Society, 112(11), 4528-4531 (1990)
Joanna Magielse et al.
Journal of ethnopharmacology, 146(1), 250-256 (2013-01-08)
The isolation of D-pinitol (or 3-O-methyl-D-chiro-inositol) from an aqueous decoction of Desmodium adscendens (Fabaceae) leaves and twigs is reported. The protective and curative effect of this decoction, in which d-pinitol was quantified, and of pure D-pinitol, against chemically-induced liver damage
Selvaraj Sivakumar et al.
Chemico-biological interactions, 188(1), 237-245 (2010-07-21)
Oxidative stress plays a crucial role in the progression and development of diabetes and its complications due to chronic hyperglycemia. The present study was aimed to investigate the kidney tissue protective nature of d-pinitol, a cyclitol present in soybean, by
Binika Hada et al.
The journals of gerontology. Series A, Biological sciences and medical sciences, 68(3), 226-234 (2012-07-31)
D-chiro-inositol, a member of the inositol family, and pinitol, a 3-methoxy analogue of D-chiro-inositol, have been proposed to have antidiabetic, antiinflammatory, anticancer and stamina enhancing effects. We found that supplementing the diet of Drosophila with D-chiro-inositol and pinitol extended adult
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