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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
Pricing and availability is not currently available.

Quality Level

100

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.[1]

Application

D-pinitol may be used as a starting material to prepare its azole nucleoside analogs.[2] 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.[1]
Precursor to biologically active fluorinated isosteres of inositol, which show cell growth inhibitory properties.[3] Has shown antidiabetic properties in mice.[4] Believed to be a salt stress regulator in a wide range of plants.[5]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9579
BCCJ5184
BCCG4570
BCCB9551
BCBW4445

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Quercetin ≥95% (HPLC), solid

Sigma-Aldrich

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
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
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
Selvaraj Sivakumar et al.
General physiology and biophysics, 28(3), 233-241 (2009-12-29)
During diabetes mellitus, endogenous hepatic glucose production is increased as a result of impaired activities of the key enzymes of carbohydrate metabolism, which leads to the condition known as hyperglycemia. D-pinitol, a bioactive constituent isolated from soybeans, has been shown
Kozikowski, A.P. et al.
Journal of the American Chemical Society, 112, 4528-4528 (1990)
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Questions

1–2 of 2 Questions  

  1. Should it be stored at room temperature or refrigerated(4ºC)?

    1 answer

    1. This product is stored at room temperature.

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  2. The information provided suggests that D-pinitol is soluble in water (H2O) or DMSO ?

    1 answer

    1. This product is not tested for solubility, however various sources report that D-Pinitol is soluble in both DMSO and water. Higher concentrations have been achieved using DMSO (up to 125 mg/mL) while marginal rates are observed with water and aqueous buffers (approx. 5 mg/mL).

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