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
(-)-QuebrachitolHMDB
1l-2-O-Methyl-chiro-inositolHMDB
2-O-Methyl-L-chiro-inositolHMDB
QuebrachitolHMDB
1L-2-O-methyl-chiro-inositolbiospider
Inositol, 2-O-methyl-, L-chiro-biospider
L-chiro-Inositol, 2-O-methyl-biospider
L-Quebrachitoldb_source
Quebrachitol, (-)-biospider
Predicted Properties
PropertyValueSource
Water Solubility544 g/LALOGPS
logP-2.7ALOGPS
logP-3.1ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.53 m³·mol⁻¹ChemAxon
Polarizability17.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H14O6
IUPAC name(1R,2S,3S,4S,5R,6R)-6-methoxycyclohexane-1,2,3,4,5-pentol
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
Description Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Polyol
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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-MS
TypeDescriptionSplash KeyView
GC-MSL-Quebrachitol, non-derivatized, GC-MS Spectrumsplash10-066r-1793000000-bc79b0c3d616f4143f86Spectrum
GC-MSL-Quebrachitol, non-derivatized, GC-MS Spectrumsplash10-066r-1793000000-bc79b0c3d616f4143f86Spectrum
Predicted GC-MSL-Quebrachitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0h7i-4900000000-a49a1a34000c6d029ba2Spectrum
Predicted GC-MSL-Quebrachitol, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009m-7131590000-80d056ae2a5ea151f252Spectrum
Predicted GC-MSL-Quebrachitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Quebrachitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0006-0900000000-1ce4425a0b0cfc34ca39Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0006-0900000000-44fd82cd8dc60277e8fcSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0006-1900000000-25d6598e8859b672af03Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0006-2900000000-ca8f3b92cdb5acf778a2Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0536-3900000000-108f6399b1e9a18df6e0Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0536-5900000000-5e58d66f26e25cfb75acSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-053u-7900000000-f0c18a8ff46d233e4d65Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-053r-9800000000-6fc4f22a443cc73e5591Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-001i-9600000000-ec4617241721d864d2ffSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-001i-9300000000-ea89f1f1ee62b3e7b0bcSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-001i-9100000000-ff58f8d612bf11cc4282Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-0bu0-4900000000-4c9bd62fe8a94e82fbd6Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-001i-9000000000-fc527ff9b17df8a45f5dSpectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-001i-9000000000-b6dea9b9985488301af8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-03di-0090000000-328674f186db37d3b072Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-03di-0290000000-152601d8c3d3fb4a0f9bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-0690000000-f565a4869dd822c41271Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0bt9-1950000000-99182114e2b761fbe8bbSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0a59-7910000000-22057a91f9a822d9adb5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-bb4d2ecdce0dc04b10afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-49945a3e6e17b3711a45Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05di-7900000000-0e8b87d7385a80fa9e17Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-93626cc17042696dcb3dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1900000000-87660e9bdc5010035071Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05dr-9500000000-eaebcb725f72fdacd030Spectrum
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).