Date published: 2025-10-15

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alpha-Pinene Oxide (CAS 1686-14-2)

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Alternate Names:
2,3-Epoxypinane
CAS Number:
1686-14-2
Molecular Weight:
152.23
Molecular Formula:
C10H16O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Alpha-pinene oxide is an oxidized derivative of the monoterpene alpha-pinene and serves as a valuable compound in organic chemistry research due to its unique reactivity. It is a key intermediate in the study of terpene metabolism, aiding in elucidating the pathways through which terpenes are transformed in both biological systems and industrial processes. Researchers utilize alpha-pinene oxide to explore ring-opening reactions catalyzed by acid or base, which is fundamental for synthetic applications. In the field of green chemistry, this compound is also investigated for its potential as a starting material in the synthesis of biodegradable polymers and environmentally friendly solvents. Additionally, its role in the synthesis of flavor and fragrance chemicals is significant, as it can be converted into compounds with different olfactory characteristics.


alpha-Pinene Oxide (CAS 1686-14-2) References

  1. Optimization of isonovalal production from alpha-pinene oxide using permeabilized cells of Pseudomonas rhodesiae CIP 107491.  |  Fontanille, P. and Larroche, C. 2003. Appl Microbiol Biotechnol. 60: 534-40. PMID: 12536252
  2. Degradation of alpha-pinene oxide and [2H7]-2,5,6-trimethyl-hept-(2E)-enoic acid by Pseudomonas fluorescens NCIMB 11761.  |  Zorn, H., et al. 2004. J Biotechnol. 107: 255-63. PMID: 14736461
  3. A membrane bioreactor for the biotransformation of alpha-pinene oxide to isonovalal by Pseudomonas fluorescens NCIMB 11671.  |  Boontawan, A. and Stuckey, DC. 2006. Appl Microbiol Biotechnol. 69: 643-9. PMID: 16088347
  4. Phosphotungstic acid as a versatile catalyst for the synthesis of fragrance compounds by alpha-pinene oxide isomerization: solvent-induced chemoselectivity.  |  da Silva Rocha, KA., et al. 2008. Chemistry. 14: 6166-72. PMID: 18512831
  5. Chirality transition in the epoxidation of (-)-alpha-pinene and successive hydrolysis studied by Raman optical activity and DFT.  |  Qiu, S., et al. 2010. Phys Chem Chem Phys. 12: 3005-13. PMID: 20449393
  6. Autoxidation of alpha-pinene at high oxygen pressure.  |  Neuenschwander, U. and Hermans, I. 2010. Phys Chem Chem Phys. 12: 10542-9. PMID: 20607162
  7. Kinetics and thermodynamics of atmospherically relevant aqueous phase reactions of α-pinene oxide.  |  Bleier, DB. and Elrod, MJ. 2013. J Phys Chem A. 117: 4223-32. PMID: 23614856
  8. Experimental Study of the Formation of Organosulfates from α-Pinene Oxidation. 2. Time Evolution and Effect of Particle Acidity.  |  Duporté, G., et al. 2020. J Phys Chem A. 124: 409-421. PMID: 31851517
  9. Phosphonate functionalized carbon spheres as Brønsted acid catalysts for the valorization of bio-renewable α-pinene oxide to trans-carveol.  |  Singh, AS., et al. 2020. Dalton Trans. 49: 7210-7217. PMID: 32420571
  10. Development and Validation of an Analytical Method for Quantitation of Alpha-Pinene Oxide in Rodent Blood and Mammary Glands by GC-MS.  |  Fernando, RA., et al. 2022. J Anal Toxicol. 46: 270-276. PMID: 33438723
  11. Toxicokinetic evaluation of the common indoor air pollutant, α-pinene, and its potential reactive metabolite, α-pinene oxide, following inhalation exposure in rodents.  |  Waidyanatha, S., et al. 2021. Toxicol Appl Pharmacol. 418: 115496. PMID: 33744279
  12. The common indoor air pollutant α-pinene is metabolised to a genotoxic metabolite α-pinene oxide.  |  Waidyanatha, S., et al. 2022. Xenobiotica. 52: 301-311. PMID: 35473450
  13. Development of rapid and selective epoxidation of α-pinene using single-step addition of H2O2 in an organic solvent-free process.  |  Mukhtar Gunam Resul, MF., et al. 2021. RSC Adv. 11: 33027-33035. PMID: 35493558
  14. Purification and properties of alpha-pinene oxide lyase from Nocardia sp. strain P18.3.  |  Griffiths, ET., et al. 1987. J Bacteriol. 169: 4980-3. PMID: 3667522
  15. The gas-phase structure determination of α-pinene oxide: An endo-cyclic epoxide of atmospheric interest.  |  Neeman, EM., et al. 2023. J Chem Phys. 158: PMID: 37094017

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

alpha-Pinene Oxide, 25 ml

sc-291876
25 ml
$90.00

alpha-Pinene Oxide, 250 ml

sc-291876A
250 ml
$430.00