(-)-chiro-Inositol
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(-)-chiro-Inositol
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CAS No:
551-72-4
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Formula:
C6H12O6
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Chemical Name:
(-)-chiro-Inositol
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Synonyms:
L-chiro-Inositol;Inositol,L-chiro-;(-)-chiro-Inositol;1L-chiro-Inositol;10215-79-9;19030-28-5
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CAS No:
Description
White crystalline powder
Myo-inositol is an inositol having myo- configuration. It has a role as a member of compatible osmolytes, a nutrient, an EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor, a human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite.|An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction. Scyllitol has been investigated for the treatment of Alzheimer Disease.|Inositol is a collection of nine different stereoisomers but the name is usually used to describe only the most common type of inositol, myo-inositol. Myo-inositol is the cis-1,2,3,5-trans-4,6-cyclohexanehexol and it is prepared from an aqueous extract of corn kernels by precipitation and hydrolysis of crude phytate. These molecules have structural similarities to glucose and are involved in cellular signaling. It is considered a pseudovitamin as it is a molecule that does not qualify to be an essential vitamin because even though its presence is vital in the body, a deficiency in this molecule does not translate into disease conditions. Inositol can be found as an ingredient of OTC products by Health Canada but all current product whose main ingredient is inositol are discontinued. By the FDA, inositol is considered in the list of specific substances affirmed as generally recognized as safe (GRAS).|D-chiro-Inositol is under investigation in clinical trial NCT03201601 (Evaluation of the Mixture Myoinositol:D-chiro-inositol 3.6:1 in Women With Polycystic Ovary Syndrome).|Scyllitol is a stereoisomer of inositol and a plant sugar alcohol found most abundantly in coconut palm trees, with potential amyloid plaque formation inhibitory activity. Following oral administration, scyllitol crosses the blood brain barrier and inhibits amyloid beta plaque formation in the brain through as of yet unknown mechanism(s). This may lead to reduced disease progression and improvement in cognitive function in patients with Alzheimer disease.|Inositol is a natural sugar found in cell membrane phospholipids, plasma lipoproteins, and (as the phosphate form) in the nucleus with potential chemopreventive properties. As one of a number of intracellular phosphate compounds, inositol is involved in cell signaling and may stimulate tumor cell differentiation. (NCI04)
(-)-chiro-Inositol Basic Attributes
180.16
180.16
209-000-7
8LQ63P85IC|63GQX5QW03|9O6Y5O4P9W|R1Y9F3N15A|6R79WV4R10|1VS4X81277|4L6452S749|4661D3JP8D|587A93P465
757076|404118|127230|103959|55558|55552|55551|45517|25142|8101
DTXSID7023146|DTXSID30110000
C122987|C28163
A - Alimentary tract and metabolism
29061390
Characteristics
121
-2.08
2.0±0.1 g/cm3
230 °C (dec.)(lit.)
291.33
143.4±21.9 °C
1.784
0.17 mg/ml
Freezer
148.2 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|128.61 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|151.95 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|144.27 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|148.6 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|131.3 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|131.5 Ų [M-H]-
Safety Information
3
36/37/38-20/21/22
26-36
Xi,Xn
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Consumption of high doses of inositol is reported to only cause some gastrointestinal effects.
It is thought that inositol can be found bound to plasma proteins.
Drug Information
Inositol may be used in food without any limitation. As a drug, inositol is used as a nutrient supplement in special dietary foods and infant formula. As it presents a relevant role in ensuring oocyte fertility, inositol has been studied for its use in the management of polycystic ovaries. Inositol is also being researched for the treatment of diabetes, prevention of metabolic syndrome, aid agent for weight loss, treatment of depression, psychiatric disorder and anxiety disorder and for prevention of cancer.
Inositol can stimulate glucose uptake in skeletal muscle cells which allows the decrease in blood sugar levels. This effect is later seen as a reduction in urine glucose concentration and indicates a decrease in high blood sugar levels. In PCOS, the administration of inositol has produced the remission of symptoms as well as a reduction in male hormone secretion, a regulation of the cholesterol level, and a more efficient fat breakdown which allow to a significant reduction on body mass and appetite. In the cases of infertility, inositol has been proven to increase sperm count and motility, as well as increase the overall quality of oocytes and embryos. In the brain, inositol has been shown to produce an increase in serotonin receptor sensitivity. This activity produces an increase in GABA release. Some of the effects observed in the brain produced a relief in symptoms of anxiety and obsessive-compulsive disorders. In high doses, it has been shown to even reduce panic attacks. In cancer research, inositol has gained interest as it can act as an antioxidant, anti-inflammatory and it seems to enhance immune properties.
Inositol is absorbed from the small intestine. In patients with inositol deficiency, the maximal plasma concentration after oral administration of inositol is registered to be of 4 hours. Inositol is taken up by the tissues via sodium-dependent inositol co-transporter which also mediates glucose uptake. Oral ingestion of inositol is registered to generate a maximal plasma concentration of 36-45 mcg.|Most of the administered dose is excreted in urine.|The pharmacokinetic profile of inositol was studied in preterm infants and the estimated volume of distribution was reported to be 0.5115 L/kg.|The pharmacokinetic profile of inositol was studied in preterm infants and the estimated clearance rate was reported to be 0.0679 L.kg/h.
It is thought that inositol is metabolized to phosphoinositol and then converted to phosphatylinositol-4,5-biphosphate which is a precursor of the second-messenger molecules. Inositol can be transformed to D-chiro-inositol via the actions of an epimerase. The normal modifications to inositol structure seem to be between all the different isomers.
The pharmacokinetic profile of inositol was studied in preterm infants and the estimated elimination half-life was reported to be of 5.22 hours.
The mechanism of action of inositol in brain disorders is not fully understood but it is thought that it may be involved in neurotransmitter synthesis and it is a precursor to the phosphatidylinositol cycle. The change that occurs in the cycle simulates when the postsynaptic receptor is activated but without activating the receptor. This activity provokes a fake activation which regulated the activity of monoamines and other neurotransmitters. Reports have shown that insulin resistance plays a key role in the clinical development of PCOS. The presence of hyperinsulinemia can induce an excess in androgen production by stimulating ovaries to produce androgens and by reducing the sex hormone binding globulin serum levels. One of the mechanisms of insulin deficiency is thought to be related to a deficiency in inositol in the inositolphosphoglycans. The administration of inositol allows it to act as a direct messenger of the insulin signaling and improves glucose tissue uptake. This mechanism is extrapolated to its functions in diabetes treatment, metabolic syndrome, and weight loss. In cancer, the mechanism of action of inositol is not fully understood. It is hypothesized that the administration of inositol increases the level of lower-phosphate inositol phosphates why can affect cycle regulation, growth, and differentiation of malignant cells. On the other hand, the formation of inositol hexaphosphate after administration of inositol presents antioxidant characteristics by the chelation of ferric ions and suppression of hydroxyl radicals.
(-)-chiro-Inositol Use and Manufacturing
Inositol: ACTIVE|myo-Inositol: ACTIVE
Cosmetics -> Antistatic; Hair conditioning; Humectant
Computed Properties
Molecular Weight:180.16
XLogP3:-3.7
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:6
Exact Mass:180.06338810
Monoisotopic Mass:180.06338810
Topological Polar Surface Area:121
Heavy Atom Count:12
Complexity:104
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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