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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 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

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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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
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
Synthesis of azole nucleoside analogues of D-pinitol as potential antitumor agents.
Zhan T and Lou H.
Carbohydrate Research, 342(6), 865-869 (2007)
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)
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
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