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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:11:55 UTC
Update Date2022-03-07 02:54:48 UTC
HMDB IDHMDB0036133
Secondary Accession Numbers
  • HMDB36133
Metabolite Identification
Common Name3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol
Description3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 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 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol.
Structure
Data?1563862826
Synonyms
ValueSource
(Menthyl)oxypropanediolHMDB
3-((L-Menthyl)oxy)propane-1,2-diolHMDB
3-L-(P-Menthane-3-yloxy)-1,2-propanediolHMDB
3-L-Menthoxypropane-1,2-diolHMDB, MeSH
3-Menthyloxy-1,2-propanediolHMDB
L-1,3-Menthoxypropane-1,2-diolHMDB
MenthoxypropanediolHMDB
Brachymelic primordial dwarfismMeSH, HMDB
Microcephalic osteodysplastic primordial dwarfism, type IMeSH, HMDB
MopdIMeSH, HMDB
Osteodysplastic primordial dwarfism, type IMeSH, HMDB
3-Menthoxypropane-1,2-diolMeSH, HMDB
Mopd 1MeSH, HMDB
Mopd1MeSH, HMDB
Taybi linder syndromeMeSH, HMDB
Taybi-linder syndromeMeSH, HMDB
Microcephalic osteodysplastic primordial dwarfism, type 1MeSH, HMDB
MopdMeSH, HMDB
Cephaloskeletal dysplasiaMeSH, HMDB
Low-birth-weight dwarfism with skeletal dysplasiaMeSH, HMDB
Mopd IMeSH, HMDB
Osteodysplastic primordial dwarfism, type 1MeSH, HMDB
Chemical FormulaC13H26O3
Average Molecular Weight230.3437
Monoisotopic Molecular Weight230.188194698
IUPAC Name3-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}propane-1,2-diol
Traditional Namementhoxypropanediol
CAS Registry Number87061-04-9
SMILES
CC(C)C1CCC(C)CC1OCC(O)CO
InChI Identifier
InChI=1S/C13H26O3/c1-9(2)12-5-4-10(3)6-13(12)16-8-11(15)7-14/h9-15H,4-8H2,1-3H3
InChI KeyMDVYIGJINBYKOM-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
  • Glycerol ether
  • Secondary 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

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point121.00 to 125.00 °C. @ 0.25 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP2.625 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP2.24ALOGPS
logP1.99ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)13.64ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.45 m³·mol⁻¹ChemAxon
Polarizability27.6 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]+154.62931661259
DarkChem[M-H]-151.12531661259
DeepCCS[M+H]+153.98330932474
DeepCCS[M-H]-151.18530932474
DeepCCS[M-2H]-187.27330932474
DeepCCS[M+Na]+162.81130932474
AllCCS[M+H]+156.732859911
AllCCS[M+H-H2O]+153.132859911
AllCCS[M+NH4]+160.032859911
AllCCS[M+Na]+160.932859911
AllCCS[M-H]-159.232859911
AllCCS[M+Na-2H]-160.132859911
AllCCS[M+HCOO]-161.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediolCC(C)C1CCC(C)CC1OCC(O)CO2296.4Standard polar33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediolCC(C)C1CCC(C)CC1OCC(O)CO1677.4Standard non polar33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediolCC(C)C1CCC(C)CC1OCC(O)CO1657.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,1TMS,isomer #1CC1CCC(C(C)C)C(OCC(CO)O[Si](C)(C)C)C11765.2Semi standard non polar33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,1TMS,isomer #2CC1CCC(C(C)C)C(OCC(O)CO[Si](C)(C)C)C11794.3Semi standard non polar33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,2TMS,isomer #1CC1CCC(C(C)C)C(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)C11832.6Semi standard non polar33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,1TBDMS,isomer #1CC1CCC(C(C)C)C(OCC(CO)O[Si](C)(C)C(C)(C)C)C12005.6Semi standard non polar33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,1TBDMS,isomer #2CC1CCC(C(C)C)C(OCC(O)CO[Si](C)(C)C(C)(C)C)C12021.3Semi standard non polar33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,2TBDMS,isomer #1CC1CCC(C(C)C)C(OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C12278.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-9410000000-98dfbfe970c670ae90682017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol GC-MS (2 TMS) - 70eV, Positivesplash10-0pi9-9423000000-721c23d46517c900aa582017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 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-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 10V, Positive-QTOFsplash10-001i-1590000000-2fadc1706d969b1f1f942016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 20V, Positive-QTOFsplash10-06s9-5950000000-9b54b9eae57a7880d8c42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 40V, Positive-QTOFsplash10-0ap0-9300000000-95c723635e5dab45c5c72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 10V, Negative-QTOFsplash10-004i-1690000000-8743ab1623786ad4be832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 20V, Negative-QTOFsplash10-0a4i-1910000000-e5047c0a6685c22bba582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 40V, Negative-QTOFsplash10-0a4r-2900000000-750bdade2186d0de64402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 10V, Positive-QTOFsplash10-01q1-9870000000-77e27c31dee07b091b212021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 20V, Positive-QTOFsplash10-000b-9500000000-5cab84e664f995a8a04e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 40V, Positive-QTOFsplash10-056s-9000000000-9af9d01094ba4af570e62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 10V, Negative-QTOFsplash10-004i-0390000000-063529b4cb405a75b4792021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 20V, Negative-QTOFsplash10-0a4i-0900000000-e3a3687bd1938e74168d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 40V, Negative-QTOFsplash10-0k9i-1900000000-d7e3e42a4a0df375082e2021-09-24Wishart 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 IDFDB014982
KNApSAcK IDNot Available
Chemspider ID4515105
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5362595
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1038341
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.