Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 02:52:10 UTC |
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Update Date | 2022-03-07 02:49:19 UTC |
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HMDB ID | HMDB0003667 |
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Secondary Accession Numbers | - HMDB0006291
- HMDB03667
- HMDB06291
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Metabolite Identification |
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Common Name | Alpha-Pinene-oxide |
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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 ). |
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Structure | InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3 |
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Synonyms | Value | Source |
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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 | 2,3-Epoxy-pinane | HMDB | 2,3-Epoxypinane | HMDB | alpha-Pinene 2,3-oxide | HMDB | alpha-Pinene oxide | HMDB | Pinene oxide | HMDB | alpha-Pinane oxide | HMDB | a-Pinene oxide | HMDB | Α-pinene oxide | HMDB | alpha-Pinene-oxide | ChEBI |
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Chemical Formula | C10H16O |
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Average Molecular Weight | 152.2334 |
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Monoisotopic Molecular Weight | 152.120115134 |
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IUPAC Name | 2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane |
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Traditional Name | α-pinene oxide |
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CAS Registry Number | 1686-14-2 |
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SMILES | CC12OC1CC1CC2C1(C)C |
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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 |
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InChI Key | NQFUSWIGRKFAHK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Bicyclic monoterpenoids |
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Alternative Parents | |
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Substituents | - Pinane monoterpenoid
- Oxepane
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 2.01 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Alpha-Pinene-oxide EI-B (Non-derivatized) | splash10-05no-9100000000-b3f5d40881aacbcfaa8f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Alpha-Pinene-oxide EI-B (Non-derivatized) | splash10-05no-9100000000-b3f5d40881aacbcfaa8f | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Alpha-Pinene-oxide GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udr-2900000000-548c439400b8d47562ba | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Alpha-Pinene-oxide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 10V, Positive-QTOF | splash10-0udi-0900000000-ddcfc606959a7449e960 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 20V, Positive-QTOF | splash10-0udr-0900000000-27f4a921f802509eb89f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 40V, Positive-QTOF | splash10-0f79-2900000000-96c60378c19c652815ce | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 10V, Negative-QTOF | splash10-0udi-0900000000-a7f6744a94ae77e3c616 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 20V, Negative-QTOF | splash10-0udi-0900000000-1ba7af232da08250f6ec | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 40V, Negative-QTOF | splash10-0f79-0900000000-67cce55b83b305c5fec0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 10V, Positive-QTOF | splash10-0udi-0900000000-0d7f2c31f0ee3340d4f0 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 20V, Positive-QTOF | splash10-0udi-0900000000-6705d62712650e316358 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 40V, Positive-QTOF | splash10-0gbi-0900000000-dce7b28402aa61559ccc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 10V, Negative-QTOF | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 20V, Negative-QTOF | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alpha-Pinene-oxide 40V, Negative-QTOF | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023213 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 82629 |
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KEGG Compound ID | C02759 |
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BioCyc ID | ALPHA-PINENE-OXIDE |
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BiGG ID | 40512 |
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Wikipedia Link | Not Available |
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METLIN ID | 6974 |
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PubChem Compound | 91508 |
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PDB ID | Not Available |
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ChEBI ID | 29060 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | 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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- 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 ]
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