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Showing Compound Isoborneol (FDB009636)

Record Information
Version1.0
Creation date2010-04-08 22:08:43 UTC
Update date2020-09-17 15:31:16 UTC
Primary IDFDB009636
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoborneol
Description(-)-Isoborneol, also known as borneol, 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 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. Borneol can be synthesized by reducing camphor by the Meerwein–Ponndorf–Verley reaction, a reversible, inexpensive process. The isomer isoborneol can be produced in the kinetically controlled reduction of camphor with sodium borohydride, which is fast and irreversible. (-)-Isoborneol is neutral compound, a white crystalline solid with a balsamic camphoreous herbal woody odor and camphoreous minty herbal earthy woody flavor ( http://www.thegoodscentscompany.com/data/rw1002092.html#toorgano). Borneol or isoborneol is a naturally occurring organic compound found in the essential oil of many plants such as camphorweed, mugwort, beautyberry, Ngai camphor, aromatic ginger .
CAS Number124-76-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
FEMA 2158HMDB
BorneolMeSH, HMDB
Isoborneol, (exo)-isomerMeSH, HMDB
Isoborneol, (1R-exo)-isomerMeSH, HMDB
Isoborneol, (endo)-isomerMeSH, HMDB
Isoborneol, (endo-(+-))-isomerMeSH, HMDB
Isoborneol, (1R-endo)-isomerMeSH, HMDB
IsoborneolMeSH, HMDB
(-)-(2R)-IsoborneolHMDB
(-)-Bornan-2-exo-olHMDB
(-)-IsoborneolHMDB
(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-olHMDB
(R,R,R)-(-)-IsoborneolHMDB
2-exo-Bornyl alcoholHMDB
Isobornyl alcoholHMDB
exo-2-Hydroxy-1,7,7-trimethylnorbornaneHMDB
l-IsoborneolPhytoBank
(±)-IsoborneolPhytoBank
dl-IsoborneolPhytoBank
NSC 26350PhytoBank
(+/-)-isoborneolbiospider
Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, exo-biospider
Borneol, exo-biospider
DL-isoborneolbiospider
exo-1,7,7-Trimethylbicyclo(2.2.1)-2-heptanolbiospider
exo-1,7,7-Trimethylbicyclo(2.2.1)heptan-2-olbiospider
exo-2-Bornanolbiospider
exo-2-Camphanolbiospider
Exoborneolbiospider
ISOBORNEOLmanual
Isoborneol, DL-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.8 g/LALOGPS
logP2.83ALOGPS
logP1.99ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.31 m³·mol⁻¹ChemAxon
Polarizability18.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H18O
IUPAC name(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
InChI IdentifierInChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
InChI KeyDTGKSKDOIYIVQL-MRTMQBJTSA-N
Isomeric SMILESCC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C2
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
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
  • Bicyclic monoterpenoid
  • Bornane 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
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical statesolid
Physical DescriptionPlates (petrol)DFC
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting PointMp 212° (sealed tube)DFC
Boiling PointNot Available
Experimental Water SolubilityPrac. insol. H2ODFC
Experimental logP3.24GRIFFIN,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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIsoborneol, non-derivatized, GC-MS Spectrumsplash10-0005-9200000000-66a44698625f85db99daSpectrum
Predicted GC-MSIsoborneol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0bt9-1900000000-561b837a8b44dbfaea56Spectrum
Predicted GC-MSIsoborneol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03k9-6930000000-42c843fe7b6dc6e988d9Spectrum
Predicted GC-MSIsoborneol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-5ca1187f552ff564ef4c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-3900000000-4d9d1609f8db2aa452262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-5900000000-96b6c2a93a81f990e5cd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000j-9800000000-e59940adf942eacbdd0e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001a-9500000000-c53784fc1bb63df575f02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0012-9300000000-7bb32334950aa43e174d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9200000000-b624a408fde0b0b95fc32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9000000000-dd98da52ad93c01d83a22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000t-9000000000-cfdbe937662b3a812a632020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00l2-9000000000-367cf23b451dbe8547462020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-017i-9000000000-fe79ebe8bd77394af3a02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0693-9000000000-b08ed9d6f97e835191b92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-05r3-9000000000-d0231d31055bf6da8fc42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-12d91b5ab3379725f8a32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-fb41d95361a6747c13942020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-59ba5428676cdc8984e32020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-7eaa92cdc2cb1dd17c332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-fb1222abb6cef74eb0832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-2900000000-622438b8bd224a755c472016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b64fc5b28acf2b8ce6ee2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-404830ee9ef93bfec2b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fki-2900000000-5d8542e9c4643c74fa542016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-4900000000-c5fb0f5b567a4f9fada92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-090r-9400000000-3329d0b3e6f71527a4bc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1ab95ec8cd37ae806b102021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJPN73-E:JFZ45-N
EAFUS ID1846
Dr. Duke IDISOBORNEOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID124-76-5
GoodScent IDrw1002091
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 herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.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
motor stimulantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).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
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
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
camphor
  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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  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.
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).