Record Information
Version1.0
Creation date2010-04-08 22:06:43 UTC
Update date2019-11-26 03:00:36 UTC
Primary IDFDB005516
Secondary Accession Numbers
  • FDB014507
  • FDB014287
Chemical Information
FooDB Nametrans-1,8-Terpin
DescriptionCis-p-menthane-1,8-diol, also known as terpin, titanium (+4) salt or terpin hydrate, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-p-menthane-1,8-diol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Cis-p-menthane-1,8-diol is a bitter tasting compound found in herbs and spices, which makes cis-p-menthane-1,8-diol a potential biomarker for the consumption of this food product. Cis-p-menthane-1,8-diol exists in all eukaryotes, ranging from yeast to humans.
CAS Number565-50-4
Structure
Thumb
Synonyms
SynonymSource
Emetine hydrochlorideHMDB
trans-p-Menthan-1,8-diolHMDB
Terpin, titanium (+4) saltMeSH
GeranodyleMeSH
2-(2'-Hydroxypropan-2'-yl)-5-methylcyclohexanolMeSH
2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanolMeSH
Terpin hydrateMeSH
Para-menthane-3,8-diolMeSH
Terpin, monohydrate(cis)-isomerMeSH
p-Menthane-1,8-diolMeSH
p-Menthane-3,8-diolMeSH
TerpinMeSH
Predicted Properties
PropertyValueSource
Water Solubility8.31 g/LALOGPS
logP1.85ALOGPS
logP1.19ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)18.93ChemAxon
pKa (Strongest Basic)-0.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.37 m³·mol⁻¹ChemAxon
Polarizability20.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H20O2
IUPAC name4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol
InChI IdentifierInChI=1S/C10H20O2/c1-9(2,11)8-4-6-10(3,12)7-5-8/h8,11-12H,4-7H2,1-3H3
InChI KeyRBNWAMSGVWEHFP-UHFFFAOYSA-N
Isomeric SMILESCC(C)(O)C1CCC(C)(O)CC1
Average Molecular Weight172.2646
Monoisotopic Molecular Weight172.146329884
Classification
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclohexanol
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9400000000-4d75197f266e6b0aa70fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fai-4924000000-e270e01b5a04f7ecddcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-93128cddee10fd3151adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-3900000000-64f7c7a52948f45f06e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ks-9500000000-ec922af015557f4afff0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-af56c59ee6ab6cb274c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-1900000000-d2509996b39e18df6112JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-5900000000-2e927a3983b03d0fd192JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDTRANS-1,8-TERPIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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 / 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).