Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:59:41 UTC
Update Date2023-02-21 17:24:34 UTC
HMDB IDHMDB0035054
Secondary Accession Numbers
  • HMDB35054
Metabolite Identification
Common Name(1S,4R)-p-Mentha-2,8-dien-1-ol
Description(1S,4R)-p-Mentha-2,8-dien-1-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 (1S,4R)-p-Mentha-2,8-dien-1-ol.
Structure
Data?1677000274
Synonyms
ValueSource
(+)-cis-P-Mentha-2,8-dien-1-olHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Traditional Name(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
CAS Registry Number22972-51-6
SMILES
CC(=C)[C@@H]1CC[C@](C)(O)C=C1
InChI Identifier
InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10+/m0/s1
InChI KeyMKPMHJQMNACGDI-VHSXEESVSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point18 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility448.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP2.58ALOGPS
logP2.03ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)18.25ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.35 m³·mol⁻¹ChemAxon
Polarizability18 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]+138.06131661259
DarkChem[M-H]-132.58431661259
DeepCCS[M+H]+136.18630932474
DeepCCS[M-H]-133.7930932474
DeepCCS[M-2H]-167.67330932474
DeepCCS[M+Na]+142.26130932474
AllCCS[M+H]+131.932859911
AllCCS[M+H-H2O]+127.432859911
AllCCS[M+NH4]+136.132859911
AllCCS[M+Na]+137.332859911
AllCCS[M-H]-135.732859911
AllCCS[M+Na-2H]-137.332859911
AllCCS[M+HCOO]-139.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(1S,4R)-p-Mentha-2,8-dien-1-olCC(=C)[C@@H]1CC[C@](C)(O)C=C11619.5Standard polar33892256
(1S,4R)-p-Mentha-2,8-dien-1-olCC(=C)[C@@H]1CC[C@](C)(O)C=C11126.2Standard non polar33892256
(1S,4R)-p-Mentha-2,8-dien-1-olCC(=C)[C@@H]1CC[C@](C)(O)C=C11131.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(1S,4R)-p-Mentha-2,8-dien-1-ol,1TMS,isomer #1C=C(C)[C@H]1C=C[C@@](C)(O[Si](C)(C)C)CC11268.6Semi standard non polar33892256
(1S,4R)-p-Mentha-2,8-dien-1-ol,1TBDMS,isomer #1C=C(C)[C@H]1C=C[C@@](C)(O[Si](C)(C)C(C)(C)C)CC11506.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-9500000000-e23ae80878d4e866f0162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol GC-MS (1 TMS) - 70eV, Positivesplash10-059l-9320000000-34c08eff2d1d5871315e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-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 - (1S,4R)-p-Mentha-2,8-dien-1-ol 10V, Positive-QTOFsplash10-0f79-0900000000-6e5429b970b50045594f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 20V, Positive-QTOFsplash10-0f79-5900000000-73d286d3392ad6eec0102016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 40V, Positive-QTOFsplash10-0gb9-9200000000-55c6fe5f6141ae3698402016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 10V, Negative-QTOFsplash10-0udi-0900000000-a931fddf6f76ffb52f182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 20V, Negative-QTOFsplash10-0udi-0900000000-e7155fded3abd51b6ea02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 40V, Negative-QTOFsplash10-0k9l-5900000000-f8457f95373cdd01f3e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 10V, Positive-QTOFsplash10-000m-8900000000-ca2176873451eccadaa12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 20V, Positive-QTOFsplash10-002f-9000000000-08f9899643afc6dea2d52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 40V, Positive-QTOFsplash10-0fvi-9000000000-dd4d2e99b68d0c5cb5a62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 20V, Negative-QTOFsplash10-0ue9-1900000000-70633168765f61f178b02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 40V, Negative-QTOFsplash10-014i-9300000000-51890339d15dded3c59d2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB013676
KNApSAcK IDC00010887
Chemspider ID9280686
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11105550
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1847361
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.