Record Information
Version1.0
Creation date2011-03-30 21:42:16 UTC
Update date2018-05-28 19:33:37 UTC
Primary IDFDB021771
Secondary Accession Numbers
  • FDB015995
  • FDB015997
Chemical Information
FooDB Name(R)-p-Mentha-1,8-dien-10-ol
Description(R)-p-Mentha-1,8-dien-10-ol, also known as 1,8-menthadien-9-ol or limonene-10-ol, 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 (R)-p-Mentha-1,8-dien-10-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number3269-90-7
Structure
Thumb
Synonyms
SynonymSource
1,8-Menthadien-9-olHMDB
1,8-p-Menthadien-10-olHMDB
1,8-p-Menthadien-9-olHMDB
1-Methyl-4-((hydroxymethyl)vinyl)-cyclohex-1-eneHMDB
4-Methyl-beta-methylene-3-cyclohexene-1-ethanolHMDB
4-Methyl-beta-methylenecyclohex-3-ene-1-ethanolHMDB
Limonene-10-olHMDB
MenthadienolHMDB
p-Menta-1,8-dien-10-olHMDB
p-Menth-1,8-dien-9-olHMDB
p-Mentha-1,8(10)dien-9-olHMDB
p-Mentha-1,8-dien-10-olHMDB
p-Mentha-1,8-dien-9-olHMDB
p-Mentha-1,8-diene-10-olHMDB
p-Menthadien-1,8-dien-9-olHMDB
(R)-Limonen-10-olmanual
(R)-Limonene-10-olmanual
Predicted Properties
PropertyValueSource
Water Solubility1.87 g/LALOGPS
logP2.55ALOGPS
logP1.94ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)16.95ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.26 m³·mol⁻¹ChemAxon
Polarizability18.5 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O
IUPAC name2-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-ol
InChI IdentifierInChI=1S/C10H16O/c1-8-3-5-10(6-4-8)9(2)7-11/h3,10-11H,2,4-7H2,1H3
InChI KeyUIMAEYMKYMNCGW-UHFFFAOYSA-N
Isomeric SMILESCC1=CCC(CC1)C(=C)CO
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
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
  • 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

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +112 (neat).; [a]20D +107 (c, 0.15 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-9400000000-10d7bb56a71d817a0a44JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9320000000-051d43346e2f43287cefJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-1900000000-3bbae5af847b65c9cbecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-7900000000-551ca5764802cd1ace26JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9200000000-f2dc607a865ea4b76971JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-f5e08fd05219f3787f7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-0900000000-8400575d268b25b0c254JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g0-8900000000-a1d665198dc2471da9e2JSpectraViewer
ChemSpider ID459498
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID527143
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37017
CRC / DFC (Dictionary of Food Compounds) IDKLW33-U:KLW34-V
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1451281
SuperScent IDNot Available
Wikipedia IDNot Available
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
clean
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus
  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