Showing Compound Card for Olivetol (CDB005799)

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Record Information
Version1.0
Created at2020-04-27 16:57:44 UTC
Updated at2021-01-04 18:49:22 UTC
CannabisDB IDCDB005799
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameOlivetol
Description5-Pentyl-1,3-benzenediol also known as 5-Pentylresorcinol or Olivetol is an alkylated derivative of 1,3-benzenediol or resorcinol. It belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 5-Pentyl-1,3-benzenediol or Olivetol is one of several structural isomers of pentyl-1,3-benzenediol wherein the pentyl group is substituted at different positions of 1,3-benzenediol. Olivetol exists as off-white crystals or olive to light purple waxy solid. Olivetol is a naturally occurring compound that is biosynthesized in various plants by a polyketide synthase (PKS)-type reaction from hexanoyl-CoA and three molecules of malonyl-CoA by an aldol condensation of a tetraketide intermediate. Olivetol can also be extracted from certain species of lichens (PMID: 24130812 ). Olivetol is produced in cannabis plant as olivetolic acid (OLA) which is a precursor in the biosynthesis of tetrahydrocannabinol (THC) ( Ref:DOI ). Olivetol is also produced by some insects as a pheromone, where it acts as a repellent or antiseptic. Olivetol is also found in cannabis smoke and is formed during the combustion of cannabis (( Ref:DOI ).). In 2009 a type III PKS known as olivetol synthase (OLS) extracted from Cannabis sativa (PMID: 19454282 ). This polyketide synthase (PKS) is a homodimeric protein that consists of a 385 amino acid polypeptide with a molecular mass of 42,585 Da that has high sequence similarity (60-70%) identity to other plant PKS's (PMID: 19454282 ). Olivetol is used in various methods to produce synthetic analogs of THC (tetrahydrocannabinol) often through a condensation reaction of olivetol and pulegone. Olivetol acts as a competitive inhibitor of the cannabinoid receptors CB1 and CB2.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,5-DihydroxyamylbenzeneChEBI
5-(1-Pentyl)resorcinolChEBI
5-N-AmylresorcinolChEBI
5-N-PentylresorcinolChEBI
5-Pentyl-1,3-benzenediolChEBI
5-PentylresorcinolChEBI
5-Pentyl-1,3-dihydroxybenzeneMeSH
Chemical FormulaC11H16O2
Average Molecular Weight180.25
Monoisotopic Molecular Weight180.115
IUPAC Name5-pentylbenzene-1,3-diol
Traditional Nameolivetol
CAS Registry Number500-66-3
SMILES
CCCCCC1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3
InChI KeyIRMPFYJSHJGOPE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentResorcinols
Alternative Parents
Substituents
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point40 to 41 °CWikipedia
Boiling Point162 to 164 °C at 5 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.16ALOGPS
logP3.66ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.36ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.46 m³·mol⁻¹ChemAxon
Polarizability20.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSOlivetol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOlivetol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-004i-0900000000-d6ab1a87cd12170e30e32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-004i-0900000000-08e75a3ec8b391af31f12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-004r-0900000000-b5bd5b70e60a159f9a972020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-000i-2900000000-6654e991c84d8be5b0232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000i-0900000000-49289c01d32c453da2532020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-004i-9000000000-95f0b83f30231c8e411e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-001i-9100000000-aacfeaee96fd163816182020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-001i-0900000000-b554d32a464b468c05bb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001i-0900000000-a85fec2fa8529fc9aa862020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001i-1900000000-96fd9aaebd08ec35aea32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-01q9-1900000000-09b64037bfc4950ebe462020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-03e9-2900000000-1e86a76d9c4d19f127f82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-03e9-2900000000-ec7f2733de2322c99f7a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-03di-3900000000-811cf0fc373fbd9993a62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-03di-2900000000-ac506bb5f76000dbc3482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-03di-3900000000-3ba96b8005bed29e98982020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-03xr-7900000000-d6a168e00e61684bd9702020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9400000000-7bf074d2c163ef0c59262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-014i-9200000000-a8ac196f569109b5689d2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-2b51125fdab1503a976c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-6900000000-31eff310f44ceb5dcc022016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-0f90bce0ab5f63155dcf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ca82e79fbf79ca0aeb5b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-7e4ce1c9c3b768b7af032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-3900000000-7394a2b1fb73433cfdbf2016-08-03View 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-11505
BiGG IDNot Available
Wikipedia LinkOlivetol
METLIN IDNot Available
PubChem Compound10377
PDB IDNot Available
ChEBI ID66960
References
General References
  1. Oettl SK, Gerstmeier J, Khan SY, Wiechmann K, Bauer J, Atanasov AG, Malainer C, Awad EM, Uhrin P, Heiss EH, Waltenberger B, Remias D, Breuss JM, Boustie J, Dirsch VM, Stuppner H, Werz O, Rollinger JM: Imbricaric acid and perlatolic acid: multi-targeting anti-inflammatory depsides from Cetrelia monachorum. PLoS One. 2013 Oct 9;8(10):e76929. doi: 10.1371/journal.pone.0076929. eCollection 2013. [PubMed:24130812 ]
  2. Taura F, Tanaka S, Taguchi C, Fukamizu T, Tanaka H, Shoyama Y, Morimoto S: Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway. FEBS Lett. 2009 Jun 18;583(12):2061-6. doi: 10.1016/j.febslet.2009.05.024. Epub 2009 May 19. [PubMed:19454282 ]