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Showing Compound Guaiol (FDB014357)

Record Information
Version1.0
Creation date2010-04-08 22:11:13 UTC
Update date2019-11-26 03:09:54 UTC
Primary IDFDB014357
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGuaiol
DescriptionGuaiol is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Guaiol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Guaiol is a mild, balsamic, and guaiacwood tasting compound found in ginger, which makes guaiol a potential biomarker for the consumption of this food product. Guaiol or champacol is an organic compound, a sesquiterpenoid alcohol found in several plants, especially in the oil of guaiacum and cypress pine. It is a crystalline solid that melts at 92 °C. Guaiol is one of many terpenes found in Cannabis .
CAS Number489-86-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-guaiolbiospider
α-guaiolbiospider
Champaca camphorbiospider
Champaca-wood oilbiospider
Champacoldb_source
Guai-1(5)-en-11-olbiospider
Guaiac alcoholbiospider
Guaiac wood oilbiospider
Guaiac wood oil (bulnesia sarmienti lor.)biospider
Guaiacwood oilbiospider
Guaioldb_source
Oils, champaca woodbiospider
Oils, essential, guaiac woodbiospider
Oils, guaiac woodbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP4.48ALOGPS
logP3.42ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)19.37ChemAxon
pKa (Strongest Basic)-0.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.24 m³·mol⁻¹ChemAxon
Polarizability27.68 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H26O
IUPAC name2-(3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl)propan-2-ol
InChI IdentifierInChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3
InChI KeyTWVJWDMOZJXUID-UHFFFAOYSA-N
Isomeric SMILESCC1CCC2=C1CC(CCC2C)C(C)(C)O
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
Classification
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.02%; H 11.78%; O 7.19%DFC
Melting PointMp 89-90°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -41 (c, 3.5 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGuaiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-5920000000-b1998e8ca3576afc9c11Spectrum
Predicted GC-MSGuaiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuaiol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuaiol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0290000000-61375dc316dc2219e1122016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ck9-1960000000-e759121787c962ebeb232016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9j-7900000000-ecaf7c0558717a19f0532016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-7141419fafebe20ba6b42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-0490000000-8376d2e7d98faa2bfbad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0c04-2920000000-037f21a9bfa03adaccd92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1490000000-8a99f36da68e1f1dcd482021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-5940000000-12e277a0b115464a78a52021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9200000000-7248db8af22b47ee88aa2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-0590000000-0ef00443a792b18059fd2021-10-12View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09676
Pubchem Compound ID227829
Pubchem Substance IDNot Available
ChEBI ID5552
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJSV90-Q:JPT46-C
EAFUS IDNot Available
Dr. Duke IDGUAIOL
BIGG IDNot Available
KNApSAcK IDC00003139
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID489-86-1
GoodScent IDrw1015101
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
termitifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
wood
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
balsamic
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
guaiacwood
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tea
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).