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Showing Compound (+)-trans-Pinocarveol (FDB014367)

Record Information
Version1.0
Creation date2010-04-08 22:11:14 UTC
Update date2020-09-17 15:36:09 UTC
Primary IDFDB014367
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(+)-trans-Pinocarveol
DescriptionTrans-Pinocarveol or simply pinocarveol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 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 plant cell 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. Trans-Pinocarveol is the (1S,3R,5S)-stereoisomer of pinocarveol. It exists as a pale, clear, yellow oil that is weakly soluble in water (1 g/L). Trans-Pinocarveol is an extremely weak basic (essentially neutral) compound, based on its pKa. It has a herbal, pine, minty or balsamic odor and a comphoreous, pine or fir needle taste. Trans-Pincarveol is found in the essential oils of hop, myssop, grapefruit, rosemary, spearmint and wormwood. It has a role as a GABA(A) modulator (PMID: 24273211), a plant metabolite, a food additive, a cosmetic/fragrance agent and a volatile oil component. With regard to its positive GABA modulating effects, Pinocarveol (along with isopulegol, verbenol, and myrtenol) are particularly potent modifiers of GABA(A) receptor function and this interaction may lead to certain sedative effects found in plants or plant oils that contain this compound (PMID: 24273211).
CAS Number19894-98-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-trans-2(10)-Pinen-3-olHMDB
(1S)-(-)-trans-PinocarveolHMDB
(1S,3R,5S)-(-)-2(10)-Pinen-3-olHMDB
L-PinocarveolHMDB
L-trans-PinocarveolHMDB
trans-(-)-PinocarveolHMDB
10-Pinen-3-olPhytoBank
2(10)-Pinen-3-olPhytoBank
6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-olPhytoBank
PinocarveolePhytoBank
trans-2(10)-Pinen-3-olPhytoBank
(±)-trans-PinocarveolPhytoBank
(+)-Pinocarveolmanual
(+)-trans-Pinocarveolbiospider
(1R)-(+)-trans-Pinocarveolmanual
(1R)-trans-Pinocarveolmanual
2(10)-Pinen-3-ol; (+)-trans-formdb_source
D-trans-Pinocarveolmanual
trans-(+)-Pinocarveolmanual
Predicted Properties
PropertyValueSource
Water Solubility1.76 g/LALOGPS
logP2.24ALOGPS
logP1.63ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)17.94ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.17 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
InChI IdentifierInChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9+/m1/s1
InChI KeyLCYXQUJDODZYIJ-VGMNWLOBSA-N
Isomeric SMILESCC1(C)[C@@H]2C[C@H]1C(=C)[C@@H](O)C2
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
Classification
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 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]25D +60.7 (c, 1.6 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-trans-Pinocarveol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0019-3900000000-6606ecc9cd06a6da5bd7Spectrum
Predicted GC-MS(+)-trans-Pinocarveol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i9-9220000000-95de3481bb916ce84e4fSpectrum
Predicted GC-MS(+)-trans-Pinocarveol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0900000000-6ff630040559510e3f1dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-b911719eff5a3760007fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-0900000000-7dde3d5da047714de193Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-1384a080edbf08e60385Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-cce040d437e6c1eee01aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0900000000-52674d0954f32b6b3004Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f53Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f53Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-5f1fa6e5001f7cc95671Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-88a021c06131e7896a30Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-b40ea28a1af5b2c22f29Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-0900000000-50f9a6a23df6edc6a85cSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID88302
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJRB55-G:JPV96-B
EAFUS IDNot Available
Dr. Duke IDTRANS-PINOCARVEOL
BIGG IDNot Available
KNApSAcK IDC00000829
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti plasmodial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).