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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:
643-12-9
Molecular Weight:
180.16
EC Number:
211-394-0
MDL number:
MFCD00272608
UNSPSC Code:
12352201
PubChem Substance ID:
24870460
NACRES:
NA.22

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

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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Modern Methods of Monosaccharide Synthesis from Non-Carbohydrate Sources.
Tomas Hudlicky et al.
Chemical reviews, 96(3), 1195-1220 (1996-05-09)
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)
Hudlicky, T. et al.
Synthesis, 897-897 (1996)
M J Berridge et al.
Nature, 341(6239), 197-205 (1989-09-21)
Inositol 1,4,5-trisphosphate is a second messenger which regulates intracellular calcium both by mobilizing calcium from internal stores and, perhaps indirectly, by stimulating calcium entry. In these actions it may function with its phosphorylated metabolite, inositol 1,3,4,5-tetrakisphosphate. The subtlety of calcium
Hudlicky, T. Cebulak, M.
Cyclitols and Their Derivatives. A Handbook of Physical, Spectral, and Synthetic Data (1993)
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