(-)-quebrachitol

L-chiro-inositol, 2-O-methyl-

CAS: 642-38-6 C7 H14 O6 MW: 194.18378000

Identification

Name(-)-quebrachitol
IUPAC(1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
CAS Number642-38-6
FDA UNII9W4JLQ7I4W
Molecular FormulaC7 H14 O6
Molecular Weight194.18378000
MDL NumberMFCD00021405
Nikkaji NumberJ16.953F

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 317.20 °C. @ 760.00 mm Hg (est)
Flash Point 294.00 °F. TCC ( 145.60 °C. ) (est)
logP (o/w) -0.740 (est)
Soluble in water, 1e+006 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for (-)-quebrachitol usage levels up tonot for fragrance use.
Recommendation for (-)-quebrachitol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

buckthorn sea buckthorn fruit mugwort plant

Synonyms

brahol L- chiro-inositol, 2-O-methyl- inositol, 2-O-methyl- inositol, 2-O-methyl-, L-chiro- (1R,2S,4S,5R)-6- methoxycyclohexane-1,2,3,4,5-pentol 2-O- methyl-L-chiro-inositol L-(-)-2-O- methylinositol L- quebrachitol PubMed: (1) H NMR analysis of O-methyl-inositol isomers: a joint experimental and theoretical study. PubMed: Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation. PubMed: Experimental and theoretical investigation of epoxide quebrachitol derivatives through spectroscopic analysis. PubMed: Cloning and characterization of a new polyol transporter (HbPLT2) in Hevea brasiliensis. PubMed: [Chemical constituents of Uvaria kurzii]. PubMed: Inositols and methylinositols in sea buckthorn (Hippophaë rhamnoides) berries. PubMed: First record of L-quebrachitol in Allophylus edulis (Sapindaceae). PubMed: Functional role of polyhydroxy compounds on protein structure and thermal stability studied by circular dichroism spectroscopy. PubMed: Deoxygenated phosphorothioate inositol phosphate analogs: synthesis, phosphatase stability, and binding affinity. PubMed: Quebrachitol-induced gastroprotection against acute gastric lesions: role of prostaglandins, nitric oxide and K+ ATP channels. PubMed: Alpha-pinene-type monoterpenes and other constituents from Artemisia suksdorfii. PubMed: Quebrachitol (2-O-methyl-L-inositol) attenuates 6-hydroxydopamine-induced cytotoxicity in rat fetal mesencephalic cell cultures. PubMed: Improved synthesis of dicyclohexylidene protected quebrachitol and its use in the synthesis of L-chiro-inositol derivatives. PubMed: 1H chemical shifts in NMR: Part 22-Prediction of the 1H chemical shifts of alcohols, diols and inositols in solution, a conformational and solvation investigation. PubMed: Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity. PubMed: Synthesis of a novel crown ether derived from chiro-inositol and its catalytic activity on the asymmetric Michael addition. PubMed: Novel PI analogues selectively block activation of the pro-survival serine/threonine kinase Akt. PubMed: Total synthesis of (-)-stevastelin B. PubMed: Proposed active constituents of Dipladenia martiana. PubMed: New syntheses of 1D- and 1L-1,2-anhydro-myo-inositol and assessment of their glycosidase inhibitory activities. PubMed: Cyclitols as cryoprotectants for spinach and chickpea thylakoids. PubMed: A versatile approach to PI(3,4)P2, PI(4,5)P2, and PI(3,4,5)P3 from L-(-)-quebrachitol. PubMed: Chlorogenic acid, an antioxidant principle from the aerial parts ofArtemisia iwayomogi that acts on 1,1-diphenyl-2-picrylhydrazyl radical. PubMed: Three new oleanane saponins from Zanha africana. PubMed: Synthesis of 1L-chiro-inositol 2,3,5-trisphosphorothioate, the first partial agonist at the platelet myo-inositol 1,4,5-trisphosphate receptor. PubMed: Synthesis and evaluation of 3-modified 1D-myo-inositols as inhibitors and substrates of phosphatidylinositol synthase and inhibitors of myo-inositol uptake by cells. PubMed: Chiral synthesis of D- and L-myo-inositol 1,4,5-trisphosphate. PubMed: Identification and possible role of D-mannitol and 2-O-methyl-chiro-inositol (quebrachitol) in Eimeria tenella. PubMed: Effects of osmotic stress on polar auxin transport in Avena mesocotyl sections. PubMed: Methane fermentation of rubber (Hevea brasiliensis) latex effluent. PubMed: The preparation of 1-O-tosyl-(--)-inositol from quebrachitol. PubMed: [STUDY OF SOME PHARMACODYNAMIC PROPERTIES OF A LAXATIVE SUBSTANCE OF PLANT ORIGIN: QUEBRACHITOL]. PubMed: [The pinitol of Coniferae and the quebrachitol of Aceraceae; search for these compounds in some other families]. PubMed: [Not Available]. PubMed: An investigation of quebrachitol as a sweetening agent for diabetics.