Terpin (YMDB01789)

Identification
YMDB IDYMDB01789
NameTerpin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Descriptiontrans-p-Menthane-1,8-diol, also known as terpin, titanium (+4) salt or emetine hydrochloride, 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. Based on a literature review a small amount of articles have been published on trans-p-Menthane-1,8-diol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-methyl-4-(1-methylethylidene)-1-cyclohexene
  • 1-methyl-4-(1-methylethylidene)cyclohexene
  • 1,4(8)-p-menthadiene
  • 1,8-Terpin
  • 4-(1-Hydroxy-1-methylethyl)-1-methylcyclohexanol
  • 4-isopropylidene-1-methylcyclohexene
  • alpha-terpinolene
  • Cyclohexanemethanol, 4-hydroxy-.alpha.,.alpha.,4-trimethyl-
  • Dipenteneglycol
  • isoterpinene
  • p-Mentha-1,8-diol
  • p-Menthane-1,8-diol
  • Terpin (VAN)
  • Terpin hydrate
  • Terpin monohydrate
  • Terpin p-menthane-1,8-diol
  • Terpinolen
  • Terpinolene
  • Emetine hydrochloride
  • trans-p-Menthan-1,8-diol
  • Terpin, titanium (+4) salt
  • Geranodyle
  • 2-(2'-Hydroxypropan-2'-yl)-5-methylcyclohexanol
  • 2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol
  • Para-menthane-3,8-diol
  • Terpin, monohydrate(cis)-isomer
  • p-Menthane-3,8-diol
  • Terpin
CAS number80-53-5
WeightAverage: 172.2646
Monoisotopic: 172.146329884
InChI KeyRBNWAMSGVWEHFP-UHFFFAOYSA-N
InChIInChI=1S/C10H20O2/c1-9(2,11)8-4-6-10(3,12)7-5-8/h8,11-12H,4-7H2,1-3H3
IUPAC Name4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol
Traditional IUPAC Nameterpin
Chemical FormulaC10H20O2
SMILESCC(C)(O)C1CCC(C)(O)CC1
Chemical Taxonomy
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
Physical Properties
StateSolid
Charge0
Melting point158 °C
Experimental Properties
PropertyValueReference
Water Solubility10 mg/mL at 20 oC [MERCK INDEX (1996)]PhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BitterFDB005516
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-32a821d6dcec9c6d8f8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-a3bfb722e34b4a8b8f05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-5900000000-ae7c494305fbab8ed7d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-3530ec21447ec3b9901eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9300000000-c8fbaad7ba0756fb340dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-9000000000-40d54f5befeaf6226257JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID9457
HMDB IDHMDB0035595
Pubchem Compound ID6651
Kegg IDC06075
ChemSpider ID6399
FOODB IDFDB005516
Wikipedia IDNot Available
BioCyc IDNot Available