Showing Compound alpha-Pinene-oxide (FDB023213)

Record Information

Version

1.0

Creation date

2011-09-21 00:26:24 UTC

Update date

2018-05-28 18:36:14 UTC

Primary ID

FDB023213

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

alpha-Pinene-oxide

Description

Alpha-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 Number

1686-14-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
2,7,7-Trimethyl-3-oxatricyclo[4.1.1.0(2,4)]octane	ChEBI
2-Pinene oxide	ChEBI
alpha-Pinene epoxide	ChEBI
a-Pinene epoxide	Generator
Α-pinene epoxide	Generator
a-Pinene-oxide	Generator
Α-pinene-oxide	Generator
alpha-Pinane oxide	MeSH
2,3-Epoxy-pinane	HMDB
2,3-Epoxypinane	HMDB
alpha-Pinene 2,3-oxide	HMDB
alpha-Pinene oxide	HMDB
Pinene oxide	HMDB
alpha-Pinene-oxide	ChEBI
a-Pinene oxide	Generator, HMDB
Α-pinene oxide	Generator, HMDB
α-pinene epoxide	Generator
α-pinene-oxide	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	2.77	ALOGPS
logP	1.98	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.41 m³·mol⁻¹	ChemAxon
Polarizability	17.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H16O

IUPAC name

2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane

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 Key

NQFUSWIGRKFAHK-UHFFFAOYSA-N

Isomeric SMILES

CC12OC1CC1CC2C1(C)C

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:29060 )
pinane monoterpenoid (CHEBI:29060 )
a small molecule (ALPHA-PINENE-OXIDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Subcellular:

Tissue and substructures:

Epidermis

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	alpha-Pinene-oxide, non-derivatized, GC-MS Spectrum	splash10-05no-9100000000-b3f5d40881aacbcfaa8f	Spectrum
GC-MS	alpha-Pinene-oxide, non-derivatized, GC-MS Spectrum	splash10-05no-9100000000-b3f5d40881aacbcfaa8f	Spectrum
Predicted GC-MS	alpha-Pinene-oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udr-2900000000-548c439400b8d47562ba	Spectrum
Predicted GC-MS	alpha-Pinene-oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-ddcfc606959a7449e960	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0900000000-27f4a921f802509eb89f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-2900000000-96c60378c19c652815ce	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-a7f6744a94ae77e3c616	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-1ba7af232da08250f6ec	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-0900000000-67cce55b83b305c5fec0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-0d7f2c31f0ee3340d4f0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-6705d62712650e316358	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbi-0900000000-dce7b28402aa61559ccc	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-25	View Spectrum