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Merck
CN

441252

Sigma-Aldrich

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.)

functional group

ether
hydroxyl

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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Nhung Thuy Dang et al.
Bioscience, biotechnology, and biochemistry, 74(5), 1062-1067 (2010-05-13)
Diabetes mellitus is a complex disease that is characterized by the defection of insulin sensitivity in such peripheral tissues as skeletal muscle, adipose tissue and liver. We have previously demonstrated that certain inositol derivatives stimulated glucose uptake accompanied by the
J. C. Thomas et al.
Plant physiology, 103(4), 1299-1304 (1993-12-01)
We selected indicators of four different metabolic processes (Crassulacean acid metabolism [CAM], amino acid and nitrogen mobilization metabolism, osmoprotection, and plant defense mechanisms) to study the relationship between salt-stress-mediated and plant growth regulator (PGR)-induced responses in Mesembryanthemum crystallinum (ice plant).
Synthesis of azole nucleoside analogues of D-pinitol as potential antitumor agents.
Zhan T and Lou H.
Carbohydrate Research, 342(6), 865-869 (2007)
Thamaraiselvan Rengarajan et al.
Journal of experimental therapeutics & oncology, 10(1), 39-49 (2012-09-06)
We have reported here that the ameliorative potentials of D-Pinitol during 7, 12-Dimethylbenz [a] anthracene induced experimental breast carcinogenesis. DMBA is a potent organ specific carcinogen which is widely employed to induce mammary carcinoma in rats. D-Pinitol a natural inositol
Selvaraj Sivakumar et al.
Free radical research, 44(6), 668-678 (2010-04-08)
The present study was aimed to investigate the effect of D-pinitol on hyperglycaemia mediated oxidative stress by analysing the hepatic antioxidant competence, pro-inflammatory cytokines and ultrastructural changes in liver tissues of streptozotocin-induced diabetic rats. Oral administration of D-pinitol (50 mg/kg

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