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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:15:37 UTC
Update Date2021-09-14 15:45:48 UTC
HMDB IDHMDB0037017
Secondary Accession Numbers
  • HMDB37017
Metabolite Identification
Common Name(R)-p-Mentha-1,8-dien-10-ol
Description(R)-p-Mentha-1,8-dien-10-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 small amount of articles have been published on (R)-p-Mentha-1,8-dien-10-ol.
Structure
Data?1563862964
Synonyms
ValueSource
1,8-Menthadien-9-olHMDB
1,8-P-Menthadien-10-olHMDB
1,8-P-Menthadien-9-olHMDB
1-Methyl-4-((hydroxymethyl)vinyl)-cyclohex-1-eneHMDB
4-Methyl-beta-methylene-3-cyclohexene-1-ethanolHMDB
4-Methyl-beta-methylenecyclohex-3-ene-1-ethanolHMDB
Limonene-10-olHMDB
MenthadienolHMDB
P-Menta-1,8-dien-10-olHMDB
P-Menth-1,8-dien-9-olHMDB
P-Mentha-1,8(10)dien-9-olHMDB
P-Mentha-1,8-dien-10-olHMDB
P-Mentha-1,8-dien-9-olHMDB
P-Mentha-1,8-diene-10-olHMDB
P-Menthadien-1,8-dien-9-olHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
IUPAC Name2-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-ol
Traditional Name2-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-ol
CAS Registry Number3269-90-7
SMILES
CC1=CCC(CC1)C(=C)CO
InChI Identifier
InChI=1S/C10H16O/c1-8-3-5-10(6-4-8)9(2)7-11/h3,10-11H,2,4-7H2,1H3
InChI KeyUIMAEYMKYMNCGW-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
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.87 g/LALOGPS
logP10(2.55) g/LALOGPS
logP10(1.94) g/LChemAxon
logS10(-1.9) g/LALOGPS
pKa (Strongest Acidic)16.95ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.26 m³·mol⁻¹ChemAxon
Polarizability18.5 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]+135.5231661259
DarkChem[M-H]-131.46931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-p-Mentha-1,8-dien-10-olCC1=CCC(CC1)C(=C)CO1975.8Standard polar33892256
(R)-p-Mentha-1,8-dien-10-olCC1=CCC(CC1)C(=C)CO1240.7Standard non polar33892256
(R)-p-Mentha-1,8-dien-10-olCC1=CCC(CC1)C(=C)CO1265.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-p-Mentha-1,8-dien-10-ol,1TMS,isomer #1C=C(CO[Si](C)(C)C)C1CC=C(C)CC11359.5Semi standard non polar33892256
(R)-p-Mentha-1,8-dien-10-ol,1TBDMS,isomer #1C=C(CO[Si](C)(C)C(C)(C)C)C1CC=C(C)CC11596.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-9400000000-10d7bb56a71d817a0a442017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9320000000-051d43346e2f43287cef2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-p-Mentha-1,8-dien-10-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 - (R)-p-Mentha-1,8-dien-10-ol 10V, Positive-QTOFsplash10-0udr-1900000000-3bbae5af847b65c9cbec2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 20V, Positive-QTOFsplash10-000i-7900000000-551ca5764802cd1ace262015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 40V, Positive-QTOFsplash10-0uxr-9200000000-f2dc607a865ea4b769712015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 10V, Negative-QTOFsplash10-0udi-0900000000-f5e08fd05219f3787f7c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 20V, Negative-QTOFsplash10-0uk9-0900000000-8400575d268b25b0c2542015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 40V, Negative-QTOFsplash10-05g0-8900000000-a1d665198dc2471da9e22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 10V, Positive-QTOFsplash10-0ukm-9800000000-3c5de0e671fd87cebe9e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 20V, Positive-QTOFsplash10-0007-9100000000-3484f9c6c6357162c82f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 40V, Positive-QTOFsplash10-0006-9000000000-229ce96908908e33db5d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 10V, Negative-QTOFsplash10-0ff0-0900000000-59979d442d155db1bde62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 20V, Negative-QTOFsplash10-00di-0900000000-d730aa0a4e04eb7b4ef32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-p-Mentha-1,8-dien-10-ol 40V, Negative-QTOFsplash10-014i-1900000000-91d37629e20269cd61e72021-09-23Wishart 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
  • 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 IDFDB021771
KNApSAcK IDC00050622
Chemspider ID459498
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound527143
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.