74137
D-chiro-Inositol
≥98.0% (HPLC)
Synonym(s):
D-(+)-chiro-Inositol, 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:
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Quality Level
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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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
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Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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
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
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
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
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
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