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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:42 UTC
Update Date2021-10-13 06:23:46 UTC
HMDB IDHMDB0032417
Secondary Accession Numbers
  • HMDB32417
Metabolite Identification
Common Name3-(L-Menthoxy)-2-methylpropane-1,2-diol
Description3-(L-Menthoxy)-2-methylpropane-1,2-diol 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 3-(L-Menthoxy)-2-methylpropane-1,2-diol.
Structure
Data?1563862260
SynonymsNot Available
Chemical FormulaC14H28O3
Average Molecular Weight244.3703
Monoisotopic Molecular Weight244.203844762
IUPAC Name2-methyl-3-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}propane-1,2-diol
Traditional Name3-[(2-isopropyl-5-methylcyclohexyl)oxy]-2-methylpropane-1,2-diol
CAS Registry Number195863-84-4
SMILES
CC(C)C1CCC(C)CC1OCC(C)(O)CO
InChI Identifier
InChI=1S/C14H28O3/c1-10(2)12-6-5-11(3)7-13(12)17-9-14(4,16)8-15/h10-13,15-16H,5-9H2,1-4H3
InChI KeyXCNCWOPROFTLGU-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
  • Glycerolipid
  • Tertiary alcohol
  • 1,2-diol
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point124.00 °C. @ 0.40 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP2.975 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP10(2.72) g/LALOGPS
logP10(2.27) g/LChemAxon
logS10(-3) g/LALOGPS
pKa (Strongest Acidic)13.46ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.09 m³·mol⁻¹ChemAxon
Polarizability29.34 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]+159.231661259
DarkChem[M-H]-154.6831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(L-Menthoxy)-2-methylpropane-1,2-diolCC(C)C1CCC(C)CC1OCC(C)(O)CO2259.0Standard polar33892256
3-(L-Menthoxy)-2-methylpropane-1,2-diolCC(C)C1CCC(C)CC1OCC(C)(O)CO1678.5Standard non polar33892256
3-(L-Menthoxy)-2-methylpropane-1,2-diolCC(C)C1CCC(C)CC1OCC(C)(O)CO1672.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(L-Menthoxy)-2-methylpropane-1,2-diol,1TMS,isomer #1CC1CCC(C(C)C)C(OCC(C)(CO)O[Si](C)(C)C)C11793.9Semi standard non polar33892256
3-(L-Menthoxy)-2-methylpropane-1,2-diol,1TMS,isomer #2CC1CCC(C(C)C)C(OCC(C)(O)CO[Si](C)(C)C)C11761.3Semi standard non polar33892256
3-(L-Menthoxy)-2-methylpropane-1,2-diol,2TMS,isomer #1CC1CCC(C(C)C)C(OCC(C)(CO[Si](C)(C)C)O[Si](C)(C)C)C11868.1Semi standard non polar33892256
3-(L-Menthoxy)-2-methylpropane-1,2-diol,1TBDMS,isomer #1CC1CCC(C(C)C)C(OCC(C)(CO)O[Si](C)(C)C(C)(C)C)C12034.8Semi standard non polar33892256
3-(L-Menthoxy)-2-methylpropane-1,2-diol,1TBDMS,isomer #2CC1CCC(C(C)C)C(OCC(C)(O)CO[Si](C)(C)C(C)(C)C)C12003.2Semi standard non polar33892256
3-(L-Menthoxy)-2-methylpropane-1,2-diol,2TBDMS,isomer #1CC1CCC(C(C)C)C(OCC(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C12315.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-9340000000-7a8e788fe1ad33718b0f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol GC-MS (2 TMS) - 70eV, Positivesplash10-0fki-9434000000-ecab34659052cd12889d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-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 - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 10V, Positive-QTOFsplash10-0002-0390000000-37220f233f51a034b9ff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 20V, Positive-QTOFsplash10-0551-4590000000-2a4a875e5efc81cc904f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 40V, Positive-QTOFsplash10-0adr-9300000000-51ebb0aac91f96b5fd392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 10V, Negative-QTOFsplash10-052f-0590000000-27073718a8fe2287de272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 20V, Negative-QTOFsplash10-0bt9-4970000000-0d8623c53ac6ddf9a1af2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 40V, Negative-QTOFsplash10-052r-1900000000-29807623969033fd1bfc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 10V, Positive-QTOFsplash10-000b-5970000000-52484109be326a5d64002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 20V, Positive-QTOFsplash10-000j-9300000000-19ff4352bf2bb41805a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 40V, Positive-QTOFsplash10-05fr-9000000000-266c5f03ecc5b0affd482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 10V, Negative-QTOFsplash10-0006-0190000000-8d8bf159339e947769fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 20V, Negative-QTOFsplash10-0a4i-0900000000-52732e299c9ed2de371e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(L-Menthoxy)-2-methylpropane-1,2-diol 40V, Negative-QTOFsplash10-0k9i-0900000000-343c2f828831b817eb582021-09-22Wishart 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 IDFDB009859
KNApSAcK IDNot Available
Chemspider ID11486376
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16734862
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1586841
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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.