468045
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
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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
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Bellington, D.C.
Chemical Society Reviews, 18, 83-83 (1989)
Modern Methods of Monosaccharide Synthesis from Non-Carbohydrate Sources.
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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
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