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D-chiro-Inositol

Cat No.:V29797 Purity: ≥98%
D-chiro-Inositol is an inositol epimer present in certain mammalian glycosylphosphatidylinositol protein anchors and inositol glycans with insulin-like bioactivity.
D-chiro-Inositol
D-chiro-Inositol Chemical Structure CAS No.: 643-12-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
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Product Description
D-chiro-Inositol is an inositol epimer present in certain mammalian glycosylphosphatidylinositol protein anchors and inositol glycans with insulin-like bioactivity. D-chiro-Inositol may be utilized in the research related to polycystic ovary syndrome (PCOS) and diabetes. D-chiro-Inositol reduces high blood sugar and improves insulin resistance.
Biological Activity I Assay Protocols (From Reference)
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Inositol is absorbed via the small intestine. In patients with inositol deficiency, peak plasma concentrations occur at 4 hours after oral administration. Inositol is absorbed by tissues via a sodium-dependent inositol cotransporter, which also participates in glucose absorption. The maximum plasma concentration of inositol after oral administration can reach 36-45 μg. Most of the administered dose is excreted in the urine. Pharmacokinetics of inositol were studied in preterm infants, with an estimated volume of distribution of 0.5115 L/kg. Pharmacokinetics of inositol were also studied in preterm infants, with an estimated clearance of 0.0679 L/kg/h. Metabolism/Metabolites It is believed that inositol is metabolized to phosphoinositol, which is then converted to phosphatidylinositol-4,5-bisphosphate, a precursor to a second messenger molecule. Inositol can be converted to D-chiral inositol by epimerase activity. Normal modifications to the inositol structure appear to exist across all the different isomers.
Biological half-life
The pharmacokinetic characteristics of inositol in preterm infants were studied, and the elimination half-life was estimated to be 5.22 hours.
Toxicity/Toxicokinetics
Protein Binding
It is believed that inositol can bind to plasma proteins.
References

[1]. A stereospecific myo-inositol/D-chiro-inositol transporter in HepG2 liver cells. Identification with D-chiro-[3-3H]inositol. J Biol Chem. 1996 Apr 26;271(17):10073-8.

[2]. D-chiro-inositol effectively attenuates cholestasis in bile duct ligated rats by improving bile acidsecretion and attenuating oxidative stress. Acta Pharmacol Sin. 2018 Feb;39(2):213-221.

[3]. chiro-Inositol Ameliorates High Fat Diet-Induced Hepatic Steatosis and Insulin Resistance viaPKCε-PI3K/AKT Pathway. J Agric Food Chem. 2019 May 29;67(21):5957-5967.

Additional Infomation
Inositol is an inositol with the inositol-configuration. It functions as a compatibility osmotic regulator, a nutrient, an EC 3.1.4.11 (phosphatidylinositol phospholipase C) inhibitor, a human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, and a mouse metabolite. Inositol is an isomer of glucose and has traditionally been considered a B vitamin, but its status as a vitamin is uncertain, and no deficiency has been found in humans. (From Martindale, The Extra Pharmacopoeia, 30th edition, p. 1379) Inositol phospholipids play an important role in signal transduction. Inositol has been investigated for the treatment of Alzheimer's disease. Inositol is a collection of nine different stereoisomers, but usually refers only to the most common type of inositol—inositol. Inositol is cis-1,2,3,5-trans-4,6-cyclohexanehexanol, prepared by precipitation and hydrolysis of crude phytic acid in a water extract of corn kernels. These molecules are structurally similar to glucose and are involved in cell signaling. It is considered a pseudovitamin because it does not meet the criteria for an essential vitamin; although it is vital in the body, a deficiency of this molecule does not cause disease. Inositol was once listed as an ingredient in over-the-counter medications by Health Canada, but all products with inositol as a primary ingredient have been discontinued. Under the U.S. Food and Drug Administration (FDA), inositol is listed as a Generally Recognized As Safe (GRAS) substance. D-chiral inositol is being investigated in the clinical trial NCT03201601 (evaluating the efficacy of an inositol:D-chiral inositol 3.6:1 mixture in women with polycystic ovary syndrome). Inositol is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain). Inositol is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain). It has also been reported to be present in tea trees, apple trees, and other organisms with relevant data. Coconut alcohol, a stereoisomer of inositol, is a plant sugar alcohol primarily found in coconut trees and possesses potential amyloid activity. It exhibits plaque formation inhibitory activity. After oral administration, coconut alcohol can cross the blood-brain barrier and inhibit the formation of β-amyloid plaques in the brain through an undefined mechanism. This may help slow disease progression and improve cognitive function in Alzheimer's patients. Inositol is a natural sugar found in cell membrane phospholipids, plasma lipoproteins, and the cell nucleus (in phosphate form), possessing potential chemopreventive properties. As one of many intracellular phosphorylated compounds, inositol participates in cell signaling and may stimulate tumor cell differentiation. (NCI04) D-chiral inositol, an isomer of inositol, may be used to improve insulin sensitivity and reproductive function. Oral administration of D-chiral inositol can improve insulin sensitivity, enhance glucose tolerance, affect reproductive hormones and function, and may regulate certain neurotransmitters. Inositol is a metabolite of Saccharomyces cerevisiae. Pharmacological Indications: Inositol can be used in unlimited quantities in food. As a drug, inositol can be used as a nutritional supplement in special dietary foods and infant formula. Because inositol plays an important role in ensuring egg fertilization, its application in the treatment of polycystic ovary syndrome (PCOS) has been investigated. Inositol is currently being investigated for the treatment of diabetes, prevention of metabolic syndrome, weight loss assistance, treatment of depression, mental illness and anxiety, and cancer prevention. Mechanism of Action: The mechanism of action of inositol in brain diseases is not fully understood, but it is generally believed that it may be involved in the synthesis of neurotransmitters and is a precursor to the phosphatidylinositol cycle. Changes occurring in this cycle mimic the situation where postsynaptic receptors are activated but not truly activated. This activity triggers a pseudoactivation, thereby regulating the activity of monoamines and other neurotransmitters. Reports indicate that insulin resistance plays a crucial role in the clinical development of polycystic ovary syndrome (PCOS). Hyperinsulinemia can induce excessive androgen production by stimulating the ovaries to produce androgens and reducing serum levels of sex hormone-binding globulin. One mechanism of insulin deficiency is thought to be related to the lack of inositol in inositol phosphoglycans. Inositol supplementation can enable it to act as a direct messenger of insulin signals and improve tissue glucose uptake. This mechanism is thought to be related to the role of inositol in diabetes treatment, metabolic syndrome, and weight loss. In cancer, the mechanism of action of inositol is not fully elucidated. It is hypothesized that inositol supplementation can increase the level of low-phosphate inositol phosphate, thereby affecting cell cycle regulation, growth, and differentiation of malignant cells. On the other hand, inositol hexaphosphate, generated after inositol supplementation, can exert antioxidant effects by chelating iron ions and inhibiting hydroxyl radicals.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H12O6
Molecular Weight
180.1559
Exact Mass
180.063
CAS #
643-12-9
PubChem CID
892
Appearance
White to off-white solid powder
Density
2.0±0.1 g/cm3
Boiling Point
291.3±40.0 °C at 760 mmHg
Melting Point
230 °C
Flash Point
143.4±21.9 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.784
LogP
-2.11
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
0
Heavy Atom Count
12
Complexity
104
Defined Atom Stereocenter Count
0
InChi Key
CDAISMWEOUEBRE-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H
Chemical Name
cyclohexane-1,2,3,4,5,6-hexol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~75 mg/mL (~416.30 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (555.06 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.5506 mL 27.7531 mL 55.5062 mL
5 mM 1.1101 mL 5.5506 mL 11.1012 mL
10 mM 0.5551 mL 2.7753 mL 5.5506 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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