(-)-quebrachitol
L-chiro-inositol, 2-O-methyl-
Identification
| Name | (-)-quebrachitol |
| IUPAC | (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol |
| CAS Number | 642-38-6 |
| FDA UNII | 9W4JLQ7I4W |
| Molecular Formula | C7 H14 O6 |
| Molecular Weight | 194.18378000 |
| MDL Number | MFCD00021405 |
| Nikkaji Number | J16.953F |
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 SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for (-)-quebrachitol usage levels up to | not for fragrance use. |
| Recommendation for (-)-quebrachitol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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.