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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:11:55 UTC
Update Date2019-07-23 06:20:26 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 is a physiological cooling agent used in food and beverage
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
3-Menthyloxy-1,2-propanediolHMDB
L-1,3-Menthoxypropane-1,2-diolHMDB
MenthoxypropanediolHMDB
Brachymelic primordial dwarfismMeSH
Microcephalic osteodysplastic primordial dwarfism, type IMeSH
MopdIMeSH
Osteodysplastic primordial dwarfism, type IMeSH
3-Menthoxypropane-1,2-diolMeSH
Mopd 1MeSH
Mopd1MeSH
Taybi linder syndromeMeSH
Taybi-linder syndromeMeSH
Microcephalic osteodysplastic primordial dwarfism, type 1MeSH
MopdMeSH
Cephaloskeletal dysplasiaMeSH
Low-birth-weight dwarfism with skeletal dysplasiaMeSH
Mopd IMeSH
Osteodysplastic primordial dwarfism, type 1MeSH
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
DescriptionThis compound 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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-9410000000-98dfbfe970c670ae9068JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0pi9-9423000000-721c23d46517c900aa58JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1590000000-2fadc1706d969b1f1f94JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06s9-5950000000-9b54b9eae57a7880d8c4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-9300000000-95c723635e5dab45c5c7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1690000000-8743ab1623786ad4be83JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-e5047c0a6685c22bba58JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-2900000000-750bdade2186d0de6440JSpectraViewer | MoNA
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
FoodDB 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
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.