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MedKoo Cat#: 598967 | Name: Piperitenone oxide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Piperitenone oxide is a major chemical constituent of the carvone pathway MS essential oil that has been reported to exhibit numerous bioactivities in cells and animals.

Chemical Structure

Piperitenone oxide
Piperitenone oxide
CAS#3564-96-3

Theoretical Analysis

MedKoo Cat#: 598967

Name: Piperitenone oxide

CAS#: 3564-96-3

Chemical Formula: C10H14O2

Exact Mass: 166.0994

Molecular Weight: 166.22

Elemental Analysis: C, 72.26; H, 8.49; O, 19.25

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Piperitenone oxide; Lippione; Rotundifolone; cis-Piperitenone epoxide; Piperitenone oxide, (+-)-;
IUPAC/Chemical Name
(1S)-6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one
InChi Key
AKASWINDKIEEBO-YHMJZVADSA-N
InChi Code
InChI=1S/C10H14O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h9H,4-5H2,1-3H3/t9-,10?/m1/s1
SMILES Code
O=C1[C@@]2([H])OC2(C)CC/C1=C(C)/C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 166.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Božović M, Pirolli A, Ragno R. Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry. Molecules. 2015 May 13;20(5):8605-33. doi: 10.3390/molecules20058605. Review. PubMed PMID: 25985361. 2: Civitelli L, Panella S, Marcocci ME, De Petris A, Garzoli S, Pepi F, Vavala E, Ragno R, Nencioni L, Palamara AT, Angiolella L. In vitro inhibition of herpes simplex virus type 1 replication by Mentha suaveolens essential oil and its main component piperitenone oxide. Phytomedicine. 2014 May 15;21(6):857-65. doi: 10.1016/j.phymed.2014.01.013. Epub 2014 Mar 11. PubMed PMID: 24629600. 3: Sousa PJ, Magalhães PJ, Lima CC, Oliveira VS, Leal-Cardoso JH. Effects of piperitenone oxide on the intestinal smooth muscle of the guinea pig. Braz J Med Biol Res. 1997 Jun;30(6):787-91. PubMed PMID: 9292118. 4: Tripathi AK, Prajapati V, Ahmad A, Aggarwal KK, Khanuja SP. Piperitenone oxide as toxic, repellent, and reproduction retardant toward malarial vector Anopheles stephensi (Diptera: Anophelinae). J Med Entomol. 2004 Jul;41(4):691-8. PubMed PMID: 15311462. 5: Lahlou S, Carneiro-Leão RF, Leal-Cardoso JH, Toscano CF. Cardiovascular effects of the essential oil of Mentha x villosa and its main constituent, piperitenone oxide, in normotensive anaesthetised rats: role of the autonomic nervous system. Planta Med. 2001 Oct;67(7):638-43. PubMed PMID: 11582542. 6: Sousa PJ, Linard CF, Azevedo-Batista D, Oliveira AC, Coelho-de-Souza AN, Leal-Cardoso JH. Antinociceptive effects of the essential oil of Mentha x villosa leaf and its major constituent piperitenone oxide in mice. Braz J Med Biol Res. 2009 Jul;42(7):655-9. PubMed PMID: 19578645. 7: Sitzmann J, Habegger R, Schnitzler WH, Grassmann J. Comparative analysis of antioxidant activities of fourteen mentha essential oils and their components. Chem Biodivers. 2014 Dec;11(12):1978-89. doi: 10.1002/cbdv.201400100. PubMed PMID: 25491341. 8: Garzoli S, Pirolli A, Vavala E, Di Sotto A, Sartorelli G, Božović M, Angiolella L, Mazzanti G, Pepi F, Ragno R. Multidisciplinary Approach to Determine the Optimal Time and Period for Extracting the Essential Oil from Mentha suaveolens Ehrh. Molecules. 2015 May 26;20(6):9640-55. doi: 10.3390/molecules20069640. PubMed PMID: 26016551. 9: Di Sotto A, Di Giacomo S, Abete L, Božović M, Parisi OA, Barile F, Vitalone A, Izzo AA, Ragno R, Mazzanti G. Genotoxicity assessment of piperitenone oxide: An in vitro and in silico evaluation. Food Chem Toxicol. 2017 Aug;106(Pt A):506-513. doi: 10.1016/j.fct.2017.06.021. Epub 2017 Jun 10. PubMed PMID: 28606765. 10: Barbieri N, Costamagna M, Gilabert M, Perotti M, Schuff C, Isla MI, Benavente A. Antioxidant activity and chemical composition of essential oils of three aromatic plants from La Rioja province. Pharm Biol. 2016;54(1):168-73. doi: 10.3109/13880209.2015.1028077. Epub 2015 Apr 13. PubMed PMID: 25865139. 11: Negro C, Notarnicola S, De Bellis L, Miceli A. Intraspecific variability of the essential oil of Calamintha nepeta subsp. nepeta from Southern Italy (Apulia). Nat Prod Res. 2013 Mar;27(4-5):331-9. doi: 10.1080/14786419.2012.691495. Epub 2012 May 30. PubMed PMID: 22646908. 12: Koliopoulos G, Pitarokili D, Kioulos E, Michaelakis A, Tzakou O. Chemical composition and larvicidal evaluation of Mentha, Salvia, and Melissa essential oils against the West Nile virus mosquito Culex pipiens. Parasitol Res. 2010 Jul;107(2):327-35. doi: 10.1007/s00436-010-1865-3. Epub 2010 Apr 20. PubMed PMID: 20405142. 13: Padalia RC, Verma RS. Comparative study of volatile oil compositions of two Plectranthus species from northern India. Nat Prod Res. 2011 Oct;25(18):1727-32. doi: 10.1080/14786419.2010.513975. Epub 2011 Jun 27. PubMed PMID: 21707228. 14: Kasrati A, Alaoui Jamali C, Bekkouche K, Spooner-Hart R, Leach D, Abbad A. Chemical characterization and insecticidal properties of essential oils from different wild populations of Mentha suaveolens subsp. timija (Briq.) Harley from Morocco. Chem Biodivers. 2015 May;12(5):823-31. doi: 10.1002/cbdv.201400236. PubMed PMID: 26010669. 15: Segev D, Nitzan N, Chaimovitsh D, Eshel A, Dudai N. Chemical and morphological diversity in wild populations of Mentha longifolia in Israel. Chem Biodivers. 2012 Mar;9(3):577-88. doi: 10.1002/cbdv.201100108. PubMed PMID: 22422525. 16: Bertoli A, Leonardi M, Krzyzanowska J, Oleszek W, Pistelli L. Mentha longifolia in vitro cultures as safe source of flavouring ingredients. Acta Biochim Pol. 2011;58(4):581-7. Epub 2011 Dec 15. PubMed PMID: 22175048. 17: Bertoli A, Leonardi M, Krzyzanowska J, Oleszek W, Pistelli L. In vitro production of M. × piperita not containing pulegone and menthofuran. Acta Biochim Pol. 2012;59(3):417-23. Epub 2012 Sep 3. PubMed PMID: 22946028. 18: Karousou R, Hanlidou E, Lazari D. Essential-oil diversity of three Calamintha species from Greece. Chem Biodivers. 2012 Jul;9(7):1364-72. doi: 10.1002/cbdv.201100262. PubMed PMID: 22782882. 19: Gudi G, Krähmer A, Krüger H, Hennig L, Schulz H. Discrimination of fennel chemotypes applying IR and Raman spectroscopy: discovery of a new γ-asarone chemotype. J Agric Food Chem. 2014 Apr 23;62(16):3537-47. doi: 10.1021/jf405752x. Epub 2014 Apr 14. PubMed PMID: 24678882. 20: Marongiu B, Piras A, Porcedda S, Falconieri D, Maxia A, Gonçalves MJ, Cavaleiro C, Salgueiro L. Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae). Nat Prod Res. 2010 Nov;24(18):1734-42. doi: 10.1080/14786410903108944. PubMed PMID: 20981614.

View History

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