Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2020-09-17 15:31:51 UTC
Primary IDFDB012526
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Quebrachitol
DescriptionL-Quebrachitol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. L-Quebrachitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, L-Quebrachitol is found, on average, in the highest concentration within sea-buckthornberries. L-Quebrachitol has also been detected, but not quantified in, mugworts. This could make L-quebrachitol a potential biomarker for the consumption of these foods. It is also found in Cannabis sativa, in Paullinia pinnata and in seabuckthorn. For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made. It shows a sweetening property half of that of sucrose but induces colic or diarrhoea at concentration used to render the food palatable. Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials. It can be found in Allophylus edulis and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping. It was first isolated by Tanret in 1887 from the bark of Aspidosperma quebracho. The substance was tested as a sweetening agent for diabetics in 1933. Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol.
CAS Number642-38-6
Structure
Thumb
Synonyms
SynonymSource
(-)-Quebrachitolbiospider
1L-2-O-methyl-chiro-inositolbiospider
2-O-Methyl-L-chiro-inositoldb_source
Inositol, 2-O-methyl-, L-chiro-biospider
L-chiro-Inositol, 2-O-methyl-biospider
L-Quebrachitoldb_source
Quebrachitolbiospider
Quebrachitol, (-)-biospider
Predicted PropertiesNot Available
Chemical FormulaC7H14O6
IUPAC name
InChI IdentifierInChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1
InChI KeyDSCFFEYYQKSRSV-FIZWYUIZSA-N
Isomeric SMILESCO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O
Average Molecular Weight194.1825
Monoisotopic Molecular Weight194.07903818
Classification
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 43.30%; H 7.27%; O 49.44%DFC
Melting PointMp 191°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -80.3 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID10254652
ChEMBL IDCHEMBL501109
KEGG Compound IDC08257
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34221
CRC / DFC (Dictionary of Food Compounds) IDBTS07-E:HHS24-P
EAFUS IDNot Available
Dr. Duke IDQUEBRACHITOL|(-)-QUERBRACHITOL
BIGG IDNot Available
KNApSAcK IDC00001169
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDQuebrachitol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).