EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

(-)-quebrachitol
L-chiro-inositol, 2-O-methyl-

Supplier Sponsors

Name:(1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
CAS Number: 642-38-6Picture of molecule3D/inchi
FDA UNII: 9W4JLQ7I4W
Nikkaji Web:J16.953F
MDL:MFCD00021405
XlogP3-AA:-3.20 (est)
Molecular Weight:194.18378000
Formula:C7 H14 O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
L-Quebrachitol 98%
BOC Sciences
For experimental / research use only.
L-Quebrachitol 98%
Odor: characteristic
Use: L-Quebrachitol is a natural product isolated from many plants, such as Hippophae rhamnoides L.
Carbosynth
For experimental / research use only.
L-Quebrachitol
ExtraSynthese
For experimental / research use only.
(-)-Quebrachitol
Glentham Life Sciences
L-Quebrachitol
Santa Cruz Biotechnology
For experimental / research use only.
L-Quebrachitol ≥98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
(-)-Quebrachitol 97%
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :151108
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
Chemidplus:0000642386
 
References:
 (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):151108
Pubchem (sid):185987046
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C08257
HMDB (The Human Metabolome Database):HMDB34221
FooDB:FDB012526
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 buckthorn sea buckthorn fruit
Search Trop Picture
 mugwort plant
Search Trop Picture
 
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
 

Articles:

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 (Hippophaƫ 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.
 
Notes:
Widely distributed in plants
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