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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 02:52:10 UTC
Update Date2021-09-14 15:18:14 UTC
HMDB IDHMDB0003667
Secondary Accession Numbers
  • HMDB0006291
  • HMDB03667
  • HMDB06291
Metabolite Identification
Common 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 ).
Structure
Data?1582752285
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
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
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane
Traditional Nameα-pinene oxide
CAS Registry Number1686-14-2
SMILES
CC12OC1CC1CC2C1(C)C
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.01Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP10(2.77) g/LALOGPS
logP10(1.98) g/LChemAxon
logS10(-3.2) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.41831661259
DarkChem[M-H]-128.76831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Alpha-Pinene-oxideCC12OC1CC1CC2C1(C)C1421.8Standard polar33892256
Alpha-Pinene-oxideCC12OC1CC1CC2C1(C)C1103.3Standard non polar33892256
Alpha-Pinene-oxideCC12OC1CC1CC2C1(C)C1109.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Alpha-Pinene-oxide EI-B (Non-derivatized)splash10-05no-9100000000-b3f5d40881aacbcfaa8f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Alpha-Pinene-oxide EI-B (Non-derivatized)splash10-05no-9100000000-b3f5d40881aacbcfaa8f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-Pinene-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-2900000000-548c439400b8d47562ba2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-Pinene-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 10V, Positive-QTOFsplash10-0udi-0900000000-ddcfc606959a7449e9602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 20V, Positive-QTOFsplash10-0udr-0900000000-27f4a921f802509eb89f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 40V, Positive-QTOFsplash10-0f79-2900000000-96c60378c19c652815ce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 10V, Negative-QTOFsplash10-0udi-0900000000-a7f6744a94ae77e3c6162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 20V, Negative-QTOFsplash10-0udi-0900000000-1ba7af232da08250f6ec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 40V, Negative-QTOFsplash10-0f79-0900000000-67cce55b83b305c5fec02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 10V, Positive-QTOFsplash10-0udi-0900000000-0d7f2c31f0ee3340d4f02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 20V, Positive-QTOFsplash10-0udi-0900000000-6705d62712650e3163582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 40V, Positive-QTOFsplash10-0gbi-0900000000-dce7b28402aa61559ccc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 20V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 40V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023213
KNApSAcK IDNot Available
Chemspider ID82629
KEGG Compound IDC02759
BioCyc IDALPHA-PINENE-OXIDE
BiGG ID40512
Wikipedia LinkNot Available
METLIN ID6974
PubChem Compound91508
PDB IDNot Available
ChEBI ID29060
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDing, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:12576684 ]
  2. 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. [PubMed:16321051 ]