Record Information
Version1.0
Creation date2010-04-08 22:11:22 UTC
Update date2019-11-26 03:10:25 UTC
Primary IDFDB014601
Secondary Accession Numbers
  • FDB007057
  • FDB003818
Chemical Information
FooDB Namep-Menth-1-en-4-ol
Descriptionp-Menth-1-en-4-ol, also known as terpinen-4-ol or 1-para-menthen-4-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. p-Menth-1-en-4-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number562-74-3
Structure
Thumb
Synonyms
SynonymSource
(+-)-p-Menth-1-en-4-olChEBI
1-Isopropyl-4-methylcyclohex-3-en-1-olChEBI
1-Menthene-4-olChEBI
1-Methyl-4-isopropyl-1-cyclohexen-4-olChEBI
1-p-Menthen-4-olChEBI
1-Para-menthen-4-olChEBI
1-Terpinen-4-olChEBI
4-CarvomenthenolChEBI
4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-olChEBI
4-Methyl-1-isopropyl-3-cyclohexen-1-olChEBI
alpha-Terpinen-4-olChEBI
Terpene-4-olChEBI
Terpin-4-en-1-olChEBI
Terpinen-4-olChEBI
Terpinene-4-olChEBI
Terpinenol-4ChEBI
Terpineol-4ChEBI
a-Terpinen-4-olGenerator
Α-terpinen-4-olGenerator
1-Isopropyl-4-methyl-3-cyclohexen-1-olHMDB
4-TerpineolHMDB
alpha -Terpinen-4-olHMDB
FEMA 2248HMDB
OriganolHMDB
p-Menth-1-en-4-olChEBI
(R)-1-Isopropyl-4-methyl-3-cyclohexen-1-olMeSH
α-Terpinen-4-olbiospider
3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-biospider
4-methyl-1-isopropyl-3-cyclohexen-1-olbiospider
Predicted Properties
PropertyValueSource
Water Solubility2.5 g/LALOGPS
logP2.81ALOGPS
logP2.33ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)20ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.31 m³·mol⁻¹ChemAxon
Polarizability18.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H18O
IUPAC name4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
InChI IdentifierInChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3
InChI KeyWRYLYDPHFGVWKC-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1(O)CCC(C)=CC1
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 77.87%; H 11.76%; O 10.37%DFC
Melting PointNot Available
Boiling PointBoiling Pt : 209 oC
Experimental Water SolubilityNot Available
Experimental logP3.26GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9100000000-575f0430fad8f36207fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-022l-9500000000-3f2e9ea1f5b3757fe0eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9100000000-575f0430fad8f36207fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-022l-9500000000-3f2e9ea1f5b3757fe0eeJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9200000000-dad36a705047932a9123JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01xc-9310000000-a2afa37a32f9557366b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-6ab97f1e60330835e91dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-6900000000-04567bac2f7cdff17fbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-9200000000-348297fc0a82a249f6ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cf6571639c99834988f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-08b8295cc319afc2225cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gw0-8900000000-e34fafe0d516af6cb77fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00dl-9200000000-42c59760ac8ce71b2738JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID10756
ChEMBL IDNot Available
KEGG Compound IDC17073
Pubchem Compound ID11230
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35833
CRC / DFC (Dictionary of Food Compounds) IDJSW58-R:JSW58-R
EAFUS ID548
Dr. Duke IDTERPINENOL-(4)|TERPIN-1-EN-4-OL|TERPINEN-1-EN-4-OL|TERPINEN-4-OL|4-TERPINEOL|TERPIN-4-EN-1-OL|1-TERPINEN-4-OL
BIGG IDNot Available
KNApSAcK IDC00029544
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID562-74-3
GoodScent IDrw1021751
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 / Bioactivities
DescriptorIDDefinitionReference
allelopathicDUKE
anti acetylcholinesterase38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti radicularDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
bacteriostatic33282 A substance that kills or slows the growth of bacteria.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
renoirritantDUKE
spermicideDUKE
vulnerary73336 A drug used in treating and healing of wounds.DUKE
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
turpentine
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
nutmeg
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
must
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
pepper
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earth
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).