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An inositol

HCID 892
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Grundinformationen

CAS
38876-99-2
Standard-SMILES
OC1C(O)C(O)C(O)C(O)C1O
InChIKey
CDAISMWEOUEBRE-UHFFFAOYSA-N
Summenformel
C6H12O6
Durchschnittliche Molmasse
180,16 g/mol
Monoisotopische Masse
180,0633881

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
An inositol
IUPAC
cyclohexane-1,2,3,4,5,6-hexol
Englischer Name
1L-chiro-Inositol
Summenformel
C6H12O6
Molmasse
180.16

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-3,7
Polarare Oberfläche (TPSA)
121 Ų
H-Brücken-Donoren
6
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
0
Schwere Atome
12
Formalladung
0
Komplexität
104

Experimentelle und physikochemische Eigenschaften

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

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]+

Physikochemische Eigenschaften

Siedepunkt
291.3 · 291.3±40.0 °C(Predicted)
Dichte
2.038 · 2.038±0.06 g/cm3(Predicted)
pka
12.63 · 12.63±0.70(Predicted)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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

Gefahrenhinweise

Regulatory Information · 6 Einträge

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 Einträge

Skin Irrit. 2 (100%)

Not Classified

Chemie und Industrie

Pharmakologische Informationen

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

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 Eintrag

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.

Zugehörige Reaktionen

27
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 6617
HRID 6617als Produktuspto-grants-2006_08
Reaktionsgleichung von HRID 20720
HRID 20720als Produktuspto-grants-2010_06
Reaktionsgleichung von HRID 20721
HRID 20721als Produktuspto-grants-2010_06
Reaktionsgleichung von HRID 161509
HRID 161509als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 339163
HRID 339163als Eduktuspto-grants-2014_11
Reaktionsgleichung von HRID 353024
HRID 353024als Eduktuspto-grants-2004_06
Reaktionsgleichung von HRID 840522
HRID 840522als Eduktuspto-grants-2002_04
Reaktionsgleichung von HRID 1019480
HRID 1019480als Produktuspto-grants-2014_05
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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 Eintrag

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 Einträge

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.

Verwendung und Herstellung

Use ClassificationCosmetics -> Hair conditioning; Humectant; Antistatic

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Fytinsure