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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:
10284-63-6
Molecular Weight:
194.18
MDL number:
MFCD00216659
UNSPSC Code:
12352112
PubChem Substance ID:
24867648
NACRES:
NA.22

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Q4951

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Shan-Chi Liu et al.
International immunopharmacology, 12(3), 494-500 (2012-01-25)
Numerous studies have indicated that inflammatory cytokines play a major role in osteoclastogenesis, leading to the bone resorption that is frequently associated with osteoporosis. D-pinitol, a 3-methoxy analogue of D-chiroinositol, was identified as an active principle in soy foods and
Synthesis of azole nucleoside analogues of D-pinitol as potential antitumor agents.
Zhan T and Lou H.
Carbohydrate Research, 342(6), 865-869 (2007)
A Llanes et al.
Plant biology (Stuttgart, Germany), 15 Suppl 1, 118-125 (2012-07-04)
The success of Prosopis strombulifera in growing under high NaCl concentrations involves a carefully controlled balance among different processes, including compartmentation of Cl(-) and Na(+) in leaf vacuoles, exclusion of Na(+) in roots, osmotic adjustment and low transpiration. In contrast
Hyun Jin Kim et al.
Annals of nutrition & metabolism, 60(1), 1-5 (2011-12-20)
Pinitol is thought to mediate insulin action and improve insulin resistance. We evaluated the effects of pinitol on glycemic control, insulin resistance and adipocytokine levels in type 2 diabetic patients. A total of 66 patients with type 2 diabetes who
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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