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74137

Sigma-Aldrich

D-chiro-Inositol

≥98.0% (HPLC)

Synonyma:

D-(+)-chiro-Inositol, 1,2,4/3,5,6-Hexahydroxycyclohexane

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About This Item

Empirický vzorec (Hillův zápis):
C6H12O6
Číslo CAS:
643-12-9
Molekulová hmotnost:
180.16
EC Number:
211-394-0
MDL number:
MFCD00272608
UNSPSC Code:
12352201
PubChem Substance ID:
329765491
NACRES:
NA.25

Quality Level

100

assay

≥98.0% (HPLC)

form

solid

optical activity

[α]/D 64.0±3.0°, c = 1 in H2O

color

white

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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Související kategorie

Application


  • D-chiro-inositol in clinical practice: An extensive review by The Experts Group on Inositol in Basic and Clinical Research presents D-chiro-inositol as a valuable substance in managing conditions like polycystic ovary syndrome, highlighting its clinical applications and potential benefits in metabolic syndrome management (Dinicola et al., 2024).

  • D-chiro-inositol enhancing longevity and antioxidant capacity: A study demonstrates that D-chiro-inositol boosts antioxidant capacity and extends lifespan in Caenorhabditis elegans through the activation of Nrf-2/SKN-1 and FOXO/DAF-16 pathways, suggesting its potential for optimizing dosage in age-related health interventions (Shi et al., 2023).

Biochem/physiol Actions

Important second messenger in insulin signal transduction.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Sucrose ≥99.5% (GC), BioReagent, suitable for cell culture, suitable for insect cell culture

Sigma-Aldrich

S1888

Sucrose

myo-Inositol ≥99% (GC), BioReagent

Sigma-Aldrich

I7508

myo-Inositol

USP

USP

1379081

Calcium D,L-5-methyltetrahydrofolate

Hao-Han Chang et al.
Experimental biology and medicine (Maywood, N.J.), 240(1), 8-14 (2014-07-26)
Diabetic nephropathy is a serious complication of diabetes mellitus with a pressing need for effective metabolic markers to detect renal impairment. Of potential significance are the inositol compounds, myo-inositol (MI), and the less abundant stereoisomer, D-chiro-inositol (DCI), which are excreted
Alessandro D Genazzani et al.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology, 30(6), 438-443 (2014-03-08)
Polycystic ovary syndrome (PCOS) is a common endocrine condition that affects fertility through oligo-ovulation, hyperandrogenism and polycystic morphology of the ovaries. Since it has been demonstrated a high incidence of insulin resistance in PCOS patients, our study aimed to evaluate
Alfonsa Pizzo et al.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology, 30(3), 205-208 (2013-12-20)
Myo-inositol and D-chiro-inositol are capable of improving the ovarian function and metabolism of polycystic ovary syndrome (PCOS) patients. The aim of this work is to compare the effects of myo-inositol and D-chiro-inositol in PCOS. We enrolled 50 patients, with homogeneous
Ken-ichi Yoshida et al.
Applied and environmental microbiology, 72(2), 1310-1315 (2006-02-08)
D-chiro-inositol (DCI) is a drug candidate for the treatment of type 2 diabetes and polycystic ovary syndrome, since it improves the efficiency with which the body uses insulin and also promotes ovulation. Here, we report genetic modification of Bacillus subtilis
J E Nestler et al.
The New England journal of medicine, 340(17), 1314-1320 (1999-04-29)
Women with the polycystic ovary syndrome have insulin resistance and hyperinsulinemia, possibly because of a deficiency of a D-chiro-inositol-containing phosphoglycan that mediates the action of insulin. We hypothesized that the administration of D-chiro-inositol would replenish stores of the mediator and
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