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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:36:14 UTC
Update Date2022-03-07 02:54:34 UTC
HMDB IDHMDB0035595
Secondary Accession Numbers
  • HMDB35595
Metabolite Identification
Common Nametrans-p-Menthane-1,8-diol
Descriptiontrans-p-Menthane-1,8-diol, also known as terpin, titanium (+4) salt or emetine hydrochloride, 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 trans-p-Menthane-1,8-diol.
Structure
Data?1563862742
Synonyms
ValueSource
Emetine hydrochlorideHMDB
trans-p-Menthan-1,8-diolHMDB
Terpin, titanium (+4) saltHMDB
GeranodyleHMDB
2-(2'-Hydroxypropan-2'-yl)-5-methylcyclohexanolHMDB
2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanolHMDB
Terpin hydrateHMDB
Para-menthane-3,8-diolHMDB
Terpin, monohydrate(cis)-isomerHMDB
p-Menthane-1,8-diolHMDB
p-Menthane-3,8-diolHMDB
TerpinHMDB
Chemical FormulaC10H20O2
Average Molecular Weight172.2646
Monoisotopic Molecular Weight172.146329884
IUPAC Name4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol
Traditional Nameterpin
CAS Registry Number565-50-4
SMILES
CC(C)(O)C1CCC(C)(O)CC1
InChI Identifier
InChI=1S/C10H20O2/c1-9(2,11)8-4-6-10(3,12)7-5-8/h8,11-12H,4-7H2,1-3H3
InChI KeyRBNWAMSGVWEHFP-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
  • Cyclohexanol
  • Tertiary alcohol
  • Cyclic 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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point158 - 159 °CNot Available
Boiling Point265.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1 mg/mL at 20 °CNot Available
LogP1.070 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.31 g/LALOGPS
logP1.85ALOGPS
logP1.19ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)18.93ChemAxon
pKa (Strongest Basic)-0.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.37 m³·mol⁻¹ChemAxon
Polarizability20.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.78231661259
DarkChem[M-H]-135.77731661259
DeepCCS[M+H]+141.75130932474
DeepCCS[M-H]-138.64430932474
DeepCCS[M-2H]-175.52630932474
DeepCCS[M+Na]+151.06430932474
AllCCS[M+H]+138.932859911
AllCCS[M+H-H2O]+134.732859911
AllCCS[M+NH4]+142.832859911
AllCCS[M+Na]+144.032859911
AllCCS[M-H]-143.432859911
AllCCS[M+Na-2H]-144.932859911
AllCCS[M+HCOO]-146.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-p-Menthane-1,8-diolCC(C)(O)C1CCC(C)(O)CC12171.3Standard polar33892256
trans-p-Menthane-1,8-diolCC(C)(O)C1CCC(C)(O)CC11273.0Standard non polar33892256
trans-p-Menthane-1,8-diolCC(C)(O)C1CCC(C)(O)CC11318.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-p-Menthane-1,8-diol,1TMS,isomer #1CC1(O)CCC(C(C)(C)O[Si](C)(C)C)CC11465.8Semi standard non polar33892256
trans-p-Menthane-1,8-diol,1TMS,isomer #2CC1(O[Si](C)(C)C)CCC(C(C)(C)O)CC11485.1Semi standard non polar33892256
trans-p-Menthane-1,8-diol,2TMS,isomer #1CC1(O[Si](C)(C)C)CCC(C(C)(C)O[Si](C)(C)C)CC11542.0Semi standard non polar33892256
trans-p-Menthane-1,8-diol,1TBDMS,isomer #1CC1(O)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC11697.6Semi standard non polar33892256
trans-p-Menthane-1,8-diol,1TBDMS,isomer #2CC1(O[Si](C)(C)C(C)(C)C)CCC(C(C)(C)O)CC11707.6Semi standard non polar33892256
trans-p-Menthane-1,8-diol,2TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC11992.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - trans-p-Menthane-1,8-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9400000000-4d75197f266e6b0aa70f2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-p-Menthane-1,8-diol GC-MS (2 TMS) - 70eV, Positivesplash10-0fai-4924000000-e270e01b5a04f7ecddcb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-p-Menthane-1,8-diol 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 - trans-p-Menthane-1,8-diol 10V, Positive-QTOFsplash10-0ab9-0900000000-93128cddee10fd3151ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 20V, Positive-QTOFsplash10-0a4s-3900000000-64f7c7a52948f45f06e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 40V, Positive-QTOFsplash10-00ks-9500000000-ec922af015557f4afff02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 10V, Negative-QTOFsplash10-00di-0900000000-af56c59ee6ab6cb274c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 20V, Negative-QTOFsplash10-0fk9-1900000000-d2509996b39e18df61122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 40V, Negative-QTOFsplash10-03dj-5900000000-2e927a3983b03d0fd1922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 10V, Negative-QTOFsplash10-00di-0900000000-32a821d6dcec9c6d8f8f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 20V, Negative-QTOFsplash10-00di-0900000000-a3bfb722e34b4a8b8f052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 40V, Negative-QTOFsplash10-00di-5900000000-ae7c494305fbab8ed7d52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 10V, Positive-QTOFsplash10-052r-1900000000-3530ec21447ec3b9901e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 20V, Positive-QTOFsplash10-0002-9300000000-c8fbaad7ba0756fb340d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-p-Menthane-1,8-diol 40V, Positive-QTOFsplash10-00lr-9000000000-40d54f5befeaf62262572021-09-24Wishart 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
  • Cytoplasm
  • 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 IDFDB005516
KNApSAcK IDC00010893
Chemspider ID6399
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6651
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1126811
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.