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468045

Sigma-Aldrich

D-(+)-chiro-Inositol

95%

Synonym(s):

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

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100 MG
CN¥263.05
1 G
CN¥1,270.13

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

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Quality Level

100

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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1 of 4

This Item
74137I8132V900492
D-(+)-chiro-Inositol 95%

468045

D-(+)-chiro-Inositol

D-chiro-Inositol ≥98.0% (HPLC)

74137

D-chiro-Inositol

scyllo-Inositol ≥98%

I8132

scyllo-Inositol

myo-Inositol Vetec™, reagent grade, 99%

V900492

myo-Inositol

assay

95%

assay

≥98.0% (HPLC)

assay

≥98%

assay

99%

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

-

form

solid

form

solid

form

-

form

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

mp

230 °C (lit.)

mp

230 °C (lit.)

mp

-

mp

222-227 °C (lit.)

optical activity

[α]23/D +60°, c = 1.2 in H2O

optical activity

[α]/D 64.0±3.0°, c = 1 in H2O

optical activity

-

optical activity

-

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.[1][2][3][4][5][6]

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
    MKCQ0557
    MKCP8085
    MKCG8502
    MKBS6012V
    MKBG6465V

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    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
    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)
    Bellington, D.C.
    Chemical Society Reviews, 18, 83-83 (1989)
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