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Showing Compound p-Menthane-3,8-diol (FDB014996)

Record Information
Version1.0
Creation date2010-04-08 22:11:35 UTC
Update date2019-11-26 03:11:05 UTC
Primary IDFDB014996
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namep-Menthane-3,8-diol
DescriptionConstituent of the roots of Litsea cubeba (mountain pepper) p-Menthane-3,8-diol, also known as para-menthane-3,8-diol and PMD, is an active ingredient used in insect repellents. It smells similar to menthol and acts as a coolant. PMD is found in the oil within leaves of the Eucalyptus citriodora tree. This tree is native to Australia, but is now cultivated in many warm places around the world. This oil, when refined for use in insect repellents, is known as Oil of Lemon Eucalyptus or, more commonly, Citriodiol. Typically, Citriodiol contains 64% PMD (a mixture of the cis and trans isomers of p-menthane-3,8-diol). Citriodiol has been notified under the European Biocidal Products Directive (BPD) 98/8/EC and is currently proceeding through the registration process with the Heath and Safety Executive in the UK. It is the only natural ingredient that can now be used as an insect repellent.
CAS Number42822-86-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(1-Hydroxy-1-methylethyl)-5-methylcyclohexanolChEBI
(1Alpha,3beta,4beta)-P-Menthane-3,8-diolHMDB
2-(2-Hydroxy-2-propyl)-5-methyl-cyclohexanolHMDB
2-(2-Hydroxypropan-2-yl)-5-methylcyclohexan-1-olHMDB
2-Hydroxy-a,a,4-trimethylcyclohexanemethanol, 9ciHMDB
2-Hydroxy-alpha,alpha,4-trimethyl-cyclohexanemethanolHMDB
2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanolHMDB, MeSH
cis-1,3,trans-1,4-P-Menthane-3,8-diolHMDB
CubebaolHMDB
Isopulegol hydrateHMDB
MenthoglycolHMDB
2-(2'-Hydroxypropan-2'-yl)-5-methylcyclohexanolMeSH
Para-menthane-3,8-diolMeSH
TerpinMeSH
Terpin, titanium (+4) saltMeSH
GeranodyleMeSH
p-Menthane-1,8-diolMeSH
Terpin, monohydrate(cis)-isomerMeSH
Terpin hydrateMeSH
(1Alpha,3beta,4beta)-p-menthane-3,8-diolbiospider
2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-olbiospider
2-Hydroxy-a,a,4-trimethylcyclohexanemethanol, 9CIdb_source
Cyclohexanemethanol, 2-hydroxy-alpha,alpha,4-trimethyl-biospider
Cyclohexanol, 2-(2-hydroxy-2-propyl)-5-methyl-biospider
p-Menthane-3,8-diol, cis-1,3,trans-1,4-biospider
Predicted Properties
PropertyValueSource
Water Solubility10.6 g/LALOGPS
logP1.88ALOGPS
logP1.23ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)14.61ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.18 m³·mol⁻¹ChemAxon
Polarizability20.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H20O2
IUPAC name2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
InChI IdentifierInChI=1S/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3
InChI KeyLMXFTMYMHGYJEI-UHFFFAOYSA-N
Isomeric SMILESCC1CCC(C(O)C1)C(C)(C)O
Average Molecular Weight172.268
Monoisotopic Molecular Weight172.146329884
Classification
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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.72%; H 11.70%; O 18.58%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSp-Menthane-3,8-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-a95bb86173c9482c1e02Spectrum
Predicted GC-MSp-Menthane-3,8-diol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ug0-9334000000-bdaf947ce686a8302215Spectrum
Predicted GC-MSp-Menthane-3,8-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-2911e28dc8c47940da942015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-4900000000-e9b5e2d981a21ab5a04b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0673-9300000000-1ed667f5bf4a6b16ac2f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-2911e28dc8c47940da942015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-4900000000-e9b5e2d981a21ab5a04b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0673-9300000000-1ed667f5bf4a6b16ac2f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-2911e28dc8c47940da942015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-4900000000-e9b5e2d981a21ab5a04b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0673-9300000000-1ed667f5bf4a6b16ac2f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-4bea1ce8427b7047cf632015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h91-2900000000-e9224eecd7b298de23c12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-9600000000-e8cd68af42cbad5ac02c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-4bea1ce8427b7047cf632015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h91-2900000000-e9224eecd7b298de23c12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-9600000000-e8cd68af42cbad5ac02c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-4bea1ce8427b7047cf632015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h91-2900000000-e9224eecd7b298de23c12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-9600000000-e8cd68af42cbad5ac02c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-3900000000-3572f58e5a6e0eee59472021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05al-9300000000-089ec1c8a692f3ac53ea2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-63f4d285de9159adb2192021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-a3bfb722e34b4a8b8f052021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-cf40354d19cfb4ea91e82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0c03-9800000000-3deba816614a8d119db02021-09-24View Spectrum
NMRNot Available
ChemSpider ID484204
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID556998
Pubchem Substance IDNot Available
ChEBI ID48250
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36145
CRC / DFC (Dictionary of Food Compounds) IDJXT45-F:JXT45-F
EAFUS ID3066
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1594771
SuperScent IDNot Available
Wikipedia IDp-Menthane-3,8-diol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
minty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
eucalyptus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference