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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:51:24 UTC
Update Date2022-03-07 02:54:39 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, 1-para-menthen-4-ol or p-Menth-1-en-4-ol or 4-carvomenthenol, is an isomer of terpineol. It 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. ±-Terpinene-4-ol is a hydrophobic, largely neutral molecule that is essentially insoluble in water. It has a peppery, spicy, musty, citrus odor and a cooling woody or spicy taste. ±-Terpinene-4-ol is widely used as a flavoring agent and as a masking agent in cosmetics. ±-Terpinene-4-ol is a natural product that can be found in a number of plants, such as allspice, anise, apple, basil, cardamom, cinnamon and Melaleuca alternifolia (also called tea tree) and is the main bioactive component of tea tree oil (PMID 22083482 ). ±-Terpinene-4-ol is also one of the monoterpenes found in cannabis plants (PMID:6991645 ). Terpinen-4-ol is a potent bactericidal agent that also possess antifungal properties. In particular, it has shown in vitro activity against Staphylococcus aureus and C. albicans (PMID:27275783 ). It has also been shown that combining this natural substance and conventional drugs may help treat resistant yeast and bacterial infections. Several studies have suggested that terpinen-4-ol induces antitumor effects by selectively causing necrotic cell death and cell-cycle arrest in melanoma cell lines, or by triggering caspase-dependent apoptosis in human melanoma cells (PMID:27275783 ).
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

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point88.00 to 90.00 °C. @ 6.00 mm HgThe Good Scents Company Information System
Water Solubility386.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.26Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.69631661259
DarkChem[M-H]-131.40631661259
DeepCCS[M+H]+142.3430932474
DeepCCS[M-H]-139.22630932474
DeepCCS[M-2H]-176.16630932474
DeepCCS[M+Na]+151.63730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-Menth-1-en-4-olCC(C)C1(O)CCC(C)=CC11649.7Standard polar33892256
p-Menth-1-en-4-olCC(C)C1(O)CCC(C)=CC11174.0Standard non polar33892256
p-Menth-1-en-4-olCC(C)C1(O)CCC(C)=CC11204.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Menth-1-en-4-ol,1TMS,isomer #1CC1=CCC(O[Si](C)(C)C)(C(C)C)CC11277.7Semi standard non polar33892256
p-Menth-1-en-4-ol,1TBDMS,isomer #1CC1=CCC(O[Si](C)(C)C(C)(C)C)(C(C)C)CC11517.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - p-Menth-1-en-4-ol EI-B (Non-derivatized)splash10-006x-9100000000-575f0430fad8f36207fc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Menth-1-en-4-ol EI-B (Non-derivatized)splash10-022l-9500000000-3f2e9ea1f5b3757fe0ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Menth-1-en-4-ol EI-B (Non-derivatized)splash10-006x-9100000000-575f0430fad8f36207fc2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Menth-1-en-4-ol EI-B (Non-derivatized)splash10-022l-9500000000-3f2e9ea1f5b3757fe0ee2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Menth-1-en-4-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9200000000-dad36a705047932a91232016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Menth-1-en-4-ol GC-MS (1 TMS) - 70eV, Positivesplash10-01xc-9310000000-a2afa37a32f9557366b32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Menth-1-en-4-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Menth-1-en-4-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9200000000-42c59760ac8ce71b27382015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Menth-1-en-4-ol 20V, Negative-QTOFsplash10-0udi-9300000000-2b45d3d3c266789085c92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Menth-1-en-4-ol 10V, Negative-QTOFsplash10-0udi-2900000000-675dc6e443ac10550c9f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Menth-1-en-4-ol 40V, Negative-QTOFsplash10-001i-9000000000-53271a36732e55f24c0d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 10V, Positive-QTOFsplash10-052r-0900000000-6ab97f1e60330835e91d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 20V, Positive-QTOFsplash10-052r-6900000000-04567bac2f7cdff17fbb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 40V, Positive-QTOFsplash10-100r-9200000000-348297fc0a82a249f6ce2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 10V, Negative-QTOFsplash10-0udi-0900000000-cf6571639c99834988f82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 20V, Negative-QTOFsplash10-0udi-0900000000-08b8295cc319afc2225c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 40V, Negative-QTOFsplash10-0gw0-8900000000-e34fafe0d516af6cb77f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 10V, Positive-QTOFsplash10-000j-8900000000-442df4d2c1c1a44d9f262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 20V, Positive-QTOFsplash10-0015-9300000000-08286b81fc833490c00b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 40V, Positive-QTOFsplash10-0006-9000000000-d2fb56949f102920a8d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 10V, Negative-QTOFsplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 20V, Negative-QTOFsplash10-0udi-0900000000-317e3f90e7716a16fe352021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-4-ol 40V, Negative-QTOFsplash10-0006-9800000000-e9742125cfbf7b82348a2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1021751
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.