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An inositol

HCID 892
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
38876-99-2
Standard SMILES
OC1C(O)C(O)C(O)C(O)C1O
InChIKey
CDAISMWEOUEBRE-UHFFFAOYSA-N
Molecular formula
C6H12O6
Average molar mass
180.16 g/mol
Monoisotopic mass
180.0633881

Overview

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 mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a human metabolite and a Daphnia magna metabolite.

Names & identifiers

Preferred name
An inositol
IUPAC
cyclohexane-1,2,3,4,5,6-hexol
English name
1L-chiro-Inositol
Molecular formula
C6H12O6
Molecular weight
180.16

Names & synonyms

an inositolRefChem:1076961inositolScyllo-inositolmyo-inositolMuco-Inositolepi-InositolAllo-inositolD-chiro-Inositoli-Inositol87-89-8meso-Inositol
Show more names
643-12-91D-Chiro-inositolNeo-inositol488-59-5D-(+)-chiro-Inositolcis-Inositol1L-Chiro-inositol6917-35-7

Database identifiers

CAS
38876-99-2、488-54-0、488-55-1、488-58-4、488-59-5、551-72-4、576-63-6、643-10-7、643-12-9、6917-35-7、87-89-8
PubChem CID
892
DTXSID
DTXSID30110000
ChEMBL
CHEMBL1231671、CHEMBL1950780、CHEMBL278373、CHEMBL3976780
ChEBI
CHEBI:17268
UNII
1VS4X81277、4661D3JP8D、4L6452S749、587A93P465、63GQX5QW03、6R79WV4R10、8LQ63P85IC、9O6Y5O4P9W、M94176HJ2F、R1Y9F3N15A
EC Number
207-681-5、209-000-7、211-393-5、211-394-0
Nikkaji
J101.888D、J101.889B、J101.890F、J101.891D、J101.892B、J4.282J、J522.945F、J9.771C、J92.778C

Properties

Computed structural propertiesFilling in

XLogP
-3.7
Topological polar surface area
121 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
6
Rotatable bonds
0
Heavy atoms
12
Formal charge
0
Complexity
104

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsHair conditioning; Humectant; Antistatic
Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Collision Cross Section · 5 items

131.3 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

128.61 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

144.27 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

138.63 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

148.7 Ų [M+Na]+

Physicochemical properties

Boiling point
291.3 · 291.3±40.0 °C(Predicted)
Density
2.038 · 2.038±0.06 g/cm3(Predicted)
pka
12.63 · 12.63±0.70(Predicted)
FDA UNII
94176 HJ2F · M94176HJ2F

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 100% (4 of 4) of all reports.

Not Classified

Hazard information

Regulatory Information · 6 items

neo-Inositol: Does not have an individual approval but may be used under an appropriate group standard

muco-Inositol: Does not have an individual approval but may be used under an appropriate group standard

L-chiro-Inositol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

cis-Inositol: Does not have an individual approval but may be used under an appropriate group standard

allo-Inositol: Does not have an individual approval but may be used under an appropriate group standard

D-chiro-Inositol: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Not Classified

Chemistry & industry

Pharmacology

Protein BindingIt is thought that inositol can be found bound to plasma proteins.
Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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.

Related reactions

27 records
New reaction record
HRID 6617 reaction equation
HRID 6617As productuspto-grants-2006_08
HRID 20720 reaction equation
HRID 20720As productuspto-grants-2010_06
HRID 20721 reaction equation
HRID 20721As productuspto-grants-2010_06
HRID 161509 reaction equation
HRID 161509As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 339163 reaction equation
HRID 339163As reactantuspto-grants-2014_11
HRID 353024 reaction equation
HRID 353024As reactantuspto-grants-2004_06
HRID 840522 reaction equation
HRID 840522As reactantuspto-grants-2002_04
HRID 1019480 reaction equation
HRID 1019480As productuspto-grants-2014_05
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Compound notes

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Biological Half-LifeThe pharmacokinetic profile of inositol was studied in preterm infants and the estimated elimination half-life was reported to be of 5.22 hours.
Metabolism/Metabolites · 1 item

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.

Absorption, Distribution and Excretion · 4 items

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.

Uses & manufacturing

Use ClassificationCosmetics -> Hair conditioning; Humectant; Antistatic

Upstream & downstream products

Downstream products

Phytic acid
Additional notes · 1 item

DefinitionChEBI: 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.