Showing Compound Card for 1,8-Menthadien-4-ol (CDB000715)

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Record Information
Version1.0
Created at2020-03-19 00:52:43 UTC
Updated at2020-11-18 16:35:27 UTC
CannabisDB IDCDB000715
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1,8-Menthadien-4-ol
Description1,8-Menthadien-4-ol or p-Mentha-1,8-dien-4-ol or Limonene-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. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. 1,8-Menthadien-4-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). It exists as a pale, clear liquid and has a peppery, spicy aroma. p-Mentha-1,8-dien-4-ol has been detected, but not quantified in, several different foods, such as blackcurrants, caraway, citrus, pepper (spice), and spearmints. This could make p-mentha-1,8-dien-4-ol a potential biomarker for the consumption of these foods. p-mentha-1,8-dien-4-ol is also used as a phermone for pine bark beetles. 1,8-Menthadien-4-ol is one of the terpenoids that present only in traces in cannabis plants (PMID: 6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC10H16O
Average Molecular Weight152.24
Monoisotopic Molecular Weight152.1201
IUPAC Name(1R)-4-methyl-1-(prop-1-en-2-yl)cyclohex-3-en-1-ol
Traditional Name(1R)-4-methyl-1-(prop-1-en-2-yl)cyclohex-3-en-1-ol
CAS Registry Number3419-02-1
SMILES
CC(=C)[C@@]1(O)CCC(C)=CC1
InChI Identifier
InChI=1S/C10H16O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,11H,1,5-7H2,2-3H3/t10-/m0/s1
InChI KeyOVKDFILSBMEKLT-JTQLQIEISA-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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.42ALOGPS
logP2.06ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)19.23ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.01 m³·mol⁻¹ChemAxon
Polarizability18.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1,8-Menthadien-4-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID17218975
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16059268
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]