(1α,2β,4β,6α)-2,2,7-trimethyl-3-oxatricyclo[4.1.1.02,4]octane (CHEM045488)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:20:35 UTC
Update Date2016-11-09 01:23:21 UTC
Accession NumberCHEM045488
Identification
Common Name(1α,2β,4β,6α)-2,2,7-trimethyl-3-oxatricyclo[4.1.1.02,4]octane
ClassSmall Molecule
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).
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
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
alpha-Pinane oxideMeSH
2,3-Epoxy-pinaneHMDB
2,3-EpoxypinaneHMDB
alpha-Pinene 2,3-oxideHMDB
alpha-Pinene oxideHMDB
Pinene oxideHMDB
alpha-Pinene-oxideChEBI
a-Pinene oxideGenerator, HMDB
Α-pinene oxideGenerator, HMDB
Chemical FormulaC10H16O
Average Molecular Mass152.233 g/mol
Monoisotopic Mass152.120 g/mol
CAS Registry Number32162-27-9
IUPAC Name2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane
Traditional Nameα-pinene oxide
SMILESCC12OC1CC1CC2C1(C)C
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05no-9100000000-b3f5d40881aacbcfaa8fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05no-9100000000-b3f5d40881aacbcfaa8fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-2900000000-548c439400b8d47562baSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ddcfc606959a7449e960Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0900000000-27f4a921f802509eb89fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2900000000-96c60378c19c652815ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-a7f6744a94ae77e3c616Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-1ba7af232da08250f6ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0900000000-67cce55b83b305c5fec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-0d7f2c31f0ee3340d4f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-6705d62712650e316358Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-0900000000-dce7b28402aa61559cccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f53Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003667
FooDB IDFDB023213
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID40512
BioCyc IDALPHA-PINENE-OXIDE
METLIN ID6974
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID82629
ChEBI ID29060
PubChem Compound ID91508
Kegg Compound IDC02759
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ding, Zongbiao; Lu, Wencong; Wang, Quanrui; Tao, Fenggang; Hu, Jianliang; Yang, Yuqing. Process for the preparation of a-epoxypinane with Na percarbonate as reagent. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp.
2. Vaddi HK, Ho PC, Chan YW, Chan SY: Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum. Biol Pharm Bull. 2003 Feb;26(2):220-8.
3. Boontawan A, Stuckey DC: Mass transfer of terpenes through a silicone rubber membrane in a liquid-liquid contacting system. Biotechnol Prog. 2005 Nov-Dec;21(6):1680-7.
4. Ding, Zongbiao; Lu, Wencong; Wang, Quanrui; Tao, Fenggang; Hu, Jianliang; Yang, Yuqing. Process for the preparation of a-epoxypinane with Na percarbonate as reagent. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp.
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3667521