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Key Documents

468045

Sigma-Aldrich

D-(+)-chiro-Inositol

95%

Synonym(s):

1,2,4/3,5,6-Hexahydroxycyclohexane

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About This Item

Empirical Formula (Hill Notation):
C6H12O6
CAS Number:
Molecular Weight:
180.16
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

solid

optical activity

[α]23/D +60°, c = 1.2 in H2O

optical purity

ee: 99% (GLC)

mp

230 °C (lit.)

storage temp.

2-8°C

SMILES string

O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O

InChI

1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m0/s1

InChI key

CDAISMWEOUEBRE-LKPKBOIGSA-N

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Application

The inositols and their phosphates have been used in the development of metabolically stable insulin mediators, inhibitors, and modulators of important metabolic functions such as glycolysis. Inositols are stable to degradative enzymes in vivo because they lack a hydrolytically labile glycosidic linkage.

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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Bellington, D.C.
Chemical Society Reviews, 18, 83-83 (1989)
Recent advances in the chemistry and biochemistry of inositol phosphates of biological interest.
B V Potter
Natural product reports, 7(1), 1-24 (1990-02-01)
Modern Methods of Monosaccharide Synthesis from Non-Carbohydrate Sources.
Tomas Hudlicky et al.
Chemical reviews, 96(3), 1195-1220 (1996-05-09)
Hudlicky, T. Cebulak, M.
Cyclitols and Their Derivatives. A Handbook of Physical, Spectral, and Synthetic Data (1993)
Hudlicky, T. et al.
Synthesis, 897-897 (1996)

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