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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:14:59 UTC
Update Date2022-03-07 02:55:09 UTC
HMDB IDHMDB0037007
Secondary Accession Numbers
  • HMDB37007
Metabolite Identification
Common Namep-Menth-1-en-9-ol
Descriptionp-Menth-1-en-9-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. Based on a literature review a significant number of articles have been published on p-Menth-1-en-9-ol.
Structure
Data?1563862963
Synonyms
ValueSource
(+)-P-Menth-1-en-9-ol,mixture OF isomersHMDB
(+)-P-Mentha-1-en-9-olHMDB
(4R,8R)-(+)-P-Menth-1-en-9-olHMDB
(4R,8S)-(+)-P-Menth-1-en-9-olHMDB
2-(4-Methyl-3-cyclohexen-1-yl)-1-propanolHMDB
2-(4-Methyl-3-cycohexen-1-yl)-1-propanolHMDB
b,4-Dimethyl-3-cyclohexene-1-ethanol, 9ciHMDB
beta,4-Dimethyl-(R-(r*,r*))-3-cyclohexene-1-ethanolHMDB
beta,4-Dimethyl-3-cyclohexene-1-ethanolHMDB
beta,4-Dimethylcyclohex-3-ene-1-ethanolHMDB
Menth-1-en-9-olHMDB
P-Menth-1-ene-9-olHMDB
P-Mentha-1-en-9-olHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name2-(4-methylcyclohex-3-en-1-yl)propan-1-ol
Traditional Name2-(4-methylcyclohex-3-en-1-yl)propan-1-ol
CAS Registry Number18479-68-0
SMILES
CC(CO)C1CCC(C)=CC1
InChI Identifier
InChI=1S/C10H18O/c1-8-3-5-10(6-4-8)9(2)7-11/h3,9-11H,4-7H2,1-2H3
InChI KeyZTYHGIAOVUPAAH-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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point115.00 to 116.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility311.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.843 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.3 g/LALOGPS
logP2.81ALOGPS
logP2.21ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)17.75ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.55 m³·mol⁻¹ChemAxon
Polarizability19.22 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]+135.87431661259
DarkChem[M-H]-131.22631661259
DeepCCS[M+H]+140.6730932474
DeepCCS[M-H]-137.34530932474
DeepCCS[M-2H]-174.61230932474
DeepCCS[M+Na]+149.94130932474
AllCCS[M+H]+134.332859911
AllCCS[M+H-H2O]+129.932859911
AllCCS[M+NH4]+138.532859911
AllCCS[M+Na]+139.632859911
AllCCS[M-H]-139.932859911
AllCCS[M+Na-2H]-141.632859911
AllCCS[M+HCOO]-143.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-Menth-1-en-9-olCC(CO)C1CCC(C)=CC11829.8Standard polar33892256
p-Menth-1-en-9-olCC(CO)C1CCC(C)=CC11241.7Standard non polar33892256
p-Menth-1-en-9-olCC(CO)C1CCC(C)=CC11267.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Menth-1-en-9-ol,1TMS,isomer #1CC1=CCC(C(C)CO[Si](C)(C)C)CC11350.0Semi standard non polar33892256
p-Menth-1-en-9-ol,1TBDMS,isomer #1CC1=CCC(C(C)CO[Si](C)(C)C(C)(C)C)CC11566.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - p-Menth-1-en-9-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9400000000-53438408024a3caa6fd92016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Menth-1-en-9-ol GC-MS (1 TMS) - 70eV, Positivesplash10-0h90-9520000000-ac53bc0838aaef4f25802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Menth-1-en-9-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Menth-1-en-9-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 10V, Positive-QTOFsplash10-0a4r-1900000000-45b1a7e5543b3891d9f02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 20V, Positive-QTOFsplash10-000i-8900000000-a9ac25a82d63df6298602015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 40V, Positive-QTOFsplash10-0ldj-9200000000-6d0d48538d0035f5e7ae2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 10V, Negative-QTOFsplash10-0udi-0900000000-662fd7167387c4bcefc32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 20V, Negative-QTOFsplash10-0uk9-0900000000-34884b5761200f0d105d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 40V, Negative-QTOFsplash10-05fr-8900000000-dcc04fa637d169e52ff42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 10V, Positive-QTOFsplash10-0a4r-8900000000-3e3aa0ed07e91240a7502021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 20V, Positive-QTOFsplash10-0005-9200000000-017e94914fdb83292cf22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 40V, Positive-QTOFsplash10-00kf-9000000000-b8ac29077ccee09c42782021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 10V, Negative-QTOFsplash10-0uk9-0900000000-243df604faf48a2e86092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 20V, Negative-QTOFsplash10-00di-0900000000-afb393f52db985e227d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Menth-1-en-9-ol 40V, Negative-QTOFsplash10-05fr-1900000000-97ecb1c861bc888c1e0b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015982
KNApSAcK IDC00010933
Chemspider ID78253
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound86753
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1107931
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.