Record Information
Version1.0
Creation date2011-09-21 00:26:24 UTC
Update date2018-05-28 18:36:14 UTC
Primary IDFDB023213
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Pinene-oxide
DescriptionAlpha-pinene oxide is cheap monoterpene, which is important compound for the fragnance industry. Biocatalytic method is used to convert monoterpenes into terpenoids. The biotransformation of alpha-pinene oxide using resting cells of Pseudomonas fluorescens NCIMB 11671 produces isonovalal (cis-2-methyl-5-isopropylhexa-2,5-dienal), which is a fragrance. However, this biotransformation has technical problems including the following: alpha-pinene oxide undergoes autoxidation in water and light; it is hydrophobic and relatively toxic to the biocatalyst; and it suffers from product inhibition. the influence of other terpene byproducts on the flux of alpha-pinene oxide was investigated and found to decrease the flux into the organic phase by up to 10%. (PMID: 16321051) [HMDB]
CAS Number1686-14-2
Structure
Thumb
Synonyms
SynonymSource
2,7,7-Trimethyl-3-oxatricyclo[4.1.1.0(2,4)]octaneChEBI
2-Pinene oxideChEBI
alpha-Pinene epoxideChEBI
a-Pinene epoxideGenerator
Α-pinene epoxideGenerator
a-Pinene-oxideGenerator
Α-pinene-oxideGenerator
2,3-Epoxy-pinaneHMDB
2,3-EpoxypinaneHMDB
alpha-Pinene 2,3-oxideHMDB
alpha-Pinene oxideHMDB
Pinene oxideHMDB
alpha-Pinane oxideHMDB
a-Pinene oxideHMDB
Α-pinene oxideHMDB
alpha-Pinene-oxideChEBI
α-pinene epoxideGenerator
α-pinene-oxideGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP2.77ALOGPS
logP1.98ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.41 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane
InChI IdentifierInChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3
InChI KeyNQFUSWIGRKFAHK-UHFFFAOYSA-N
Isomeric SMILESCC12OC1CC1CC2C1(C)C
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
  • Oxepane
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
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-MSalpha-Pinene-oxide, non-derivatized, GC-MS Spectrumsplash10-05no-9100000000-b3f5d40881aacbcfaa8fSpectrum
GC-MSalpha-Pinene-oxide, non-derivatized, GC-MS Spectrumsplash10-05no-9100000000-b3f5d40881aacbcfaa8fSpectrum
Predicted GC-MSalpha-Pinene-oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udr-2900000000-548c439400b8d47562baSpectrum
Predicted GC-MSalpha-Pinene-oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ddcfc606959a7449e960Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0900000000-27f4a921f802509eb89fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2900000000-96c60378c19c652815ceSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-a7f6744a94ae77e3c616Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-1ba7af232da08250f6ecSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0900000000-67cce55b83b305c5fec0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-0d7f2c31f0ee3340d4f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-6705d62712650e316358Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-0900000000-dce7b28402aa61559cccSpectrum
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-c373c9eea3cebf186f53Spectrum
NMRNot Available
ChemSpider ID82629
ChEMBL IDCHEMBL274511
KEGG Compound IDC02759
Pubchem Compound ID91508
Pubchem Substance IDNot Available
ChEBI ID29060
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03667
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID40512
KNApSAcK IDNot Available
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference