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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:51:24 UTC
Update Date2019-07-23 06:19:39 UTC
HMDB IDHMDB0035833
Secondary Accession Numbers
  • HMDB35833
Metabolite Identification
Common Namep-Menth-1-en-4-ol
Descriptionp-Menth-1-en-4-ol, also known as terpinen-4-ol or 1-para-menthen-4-ol, 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. p-Menth-1-en-4-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862779
Synonyms
ValueSource
(+-)-p-Menth-1-en-4-olChEBI
1-Isopropyl-4-methylcyclohex-3-en-1-olChEBI
1-Menthene-4-olChEBI
1-Methyl-4-isopropyl-1-cyclohexen-4-olChEBI
1-p-Menthen-4-olChEBI
1-Para-menthen-4-olChEBI
1-Terpinen-4-olChEBI
4-CarvomenthenolChEBI
4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-olChEBI
4-Methyl-1-isopropyl-3-cyclohexen-1-olChEBI
alpha-Terpinen-4-olChEBI
Terpene-4-olChEBI
Terpin-4-en-1-olChEBI
Terpinen-4-olChEBI
Terpinene-4-olChEBI
Terpinenol-4ChEBI
Terpineol-4ChEBI
a-Terpinen-4-olGenerator
Α-terpinen-4-olGenerator
1-Isopropyl-4-methyl-3-cyclohexen-1-olHMDB
4-TerpineolHMDB
alpha -Terpinen-4-olHMDB
FEMA 2248HMDB
OriganolHMDB
p-Menth-1-en-4-olChEBI
(R)-1-Isopropyl-4-methyl-3-cyclohexen-1-olMeSH
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
Traditional Nameterpinen-4-ol
CAS Registry Number562-74-3
SMILES
CC(C)C1(O)CCC(C)=CC1
InChI Identifier
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3
InChI KeyWRYLYDPHFGVWKC-UHFFFAOYSA-N
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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.26Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.5 g/LALOGPS
logP2.81ALOGPS
logP2.33ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)20ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.31 m³·mol⁻¹ChemAxon
Polarizability18.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9100000000-575f0430fad8f36207fcSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-022l-9500000000-3f2e9ea1f5b3757fe0eeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9100000000-575f0430fad8f36207fcSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-022l-9500000000-3f2e9ea1f5b3757fe0eeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9200000000-dad36a705047932a9123Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01xc-9310000000-a2afa37a32f9557366b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-6ab97f1e60330835e91dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-6900000000-04567bac2f7cdff17fbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-9200000000-348297fc0a82a249f6ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cf6571639c99834988f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-08b8295cc319afc2225cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gw0-8900000000-e34fafe0d516af6cb77fSpectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9200000000-42c59760ac8ce71b2738Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDDB12816
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014601
KNApSAcK IDC00029544
Chemspider ID10756
KEGG Compound IDC17073
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11230
PDB IDNot Available
ChEBI ID78884
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.