Piperitenone oxide

Formula: C₁₀H₁₄O₂
Molecular weight: 166.2170
IUPAC Standard InChI: InChI=1S/C10H14O2/c1-6(2)7-4-8(11)10(3)9(5-7)12-10/h7,9H,1,4-5H2,2-3H3/t7-,9-,10+/m0/s1
IUPAC Standard InChIKey: YGMNGQDLUQECTO-UJNFCWOMSA-N
CAS Registry Number: 35178-55-3
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Stereoisomers:
- Carvone oxide, cis-
- Carvone oxide
Other names: 1,2-Epoxy-p-menth-4(8)-en-3-one; 6-Methyl-3-(1-methylethylidene)-7-oxabicyclo(4.1.0)heptan-2-one; 7-Oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethylidene)-; p-Menth-4(8)-en-3-one, 1,2-epoxy-
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Gas Chromatography

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	SE-30	1352.	Juliani, Koroch, et al., 2002	He, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_start: 60. C; T_end: 240. C
Capillary	HP-5	1363.	Kitic, Palic, et al., 2001	25. m/0.32 mm/0.52 μm, H2, 4. K/min; T_start: 40. C; T_end: 240. C

Kovats' RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	BP-1	1342.	Dwivedi, Khan, et al., 2004	25. m/0.25 mm/0.25 μm, N2; Program: 60C => 5C/min => 220C(5min) => 3C/min => 245C(5min)

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1368.	Benzo, Gilardoni, et al., 2007	30. m/0.25 mm/0.25 μm, He, 40. C @ 1. min, 5. K/min, 250. C @ 10. min
Capillary	DB-5	1363.	Flamini, Cioni, et al., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	HP-5MS	1366.	Vagionas, Ngassapa, et al., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	DB-5	1365.	Javidnia, Miri, et al., 2004	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 260. C
Capillary	HP-5	1373.	Sartoratto, Machado, et al., 2004	25. m/0.2 mm/0.33 μm, He, 3. K/min, 240. C @ 7. min; T_start: 60. C
Capillary	HP-5	1368.	Emilio Tomei, Manganelli, et al., 2003	30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; T_end: 220. C
Capillary	DB-5	1363.	Javidnia, Miri, et al., 2003	He, 4. K/min; Column length: 25. m; Column diameter: 0.25 mm; T_start: 60. C; T_end: 260. C
Capillary	SPB-1	1326.	Cavaleiro, Salgueiro, et al., 2002	30. m/0.20 mm/0.20 μm, He, 3. K/min, 220. C @ 15. min; T_start: 70. C
Capillary	BP-1	1333.	Baldovini, Ristorcelli, et al., 2000	50. m/0.22 mm/0.25 μm, 2. K/min, 220. C @ 20. min; T_start: 60. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	5 % Phenyl methyl siloxane	1369.	Sacchetti, Maietti, et al., 2005	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C (10min)
Capillary	SE-52	1386.	Lorenzo, Paz, et al., 2002	30. m/0.32 mm/0.42 μm, H2; Program: 60C(8min) => 3C/min => 180C => 20C/min => 250C(10min)

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	BP-20	1945.	Baldovini, Ristorcelli, et al., 2000	50. m/0.22 mm/0.25 μm, 2. K/min, 220. C @ 20. min; T_start: 60. C

Van Den Dool and Kratz RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1940.	Lorenzo, Paz, et al., 2002	25. m/0.32 mm/0.25 μm, H2; Program: 40C(8min) => 3C/min => 180C => 20C/min => 230C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1369.	Bertoli, Lepnardi, et al., 2011	30. m/0.25 mm/0.25 μm, Helium, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	DB-5	1363.	Coelho, Grosso, et al., 2007	30. m/0.25 mm/0.25 μm, He, 70. C @ 5. min, 3. K/min, 310. C @ 20. min
Capillary	RTX-5	1317.	Setkova, Risticevic, et al., 2007	10. m/0.18 mm/0.2 μm, He, 40. C @ 0.5 min, 50. K/min, 275. C @ 0.5 min
Capillary	HP-5 MS	1369.	Vagionas, Graikou, et al., 2007	30. m/0.25 mm/0.25 μm, Helium, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	DB-5	1330.	Yadegarinia, Gachkar, et al., 2006	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 250. C
Capillary	HP-5MS	1366.	Slavkovska, Couladis, et al., 2005	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	OV-1	1333.	De Pooter, De Buyck, et al., 1986	He, 2. K/min; T_start: 40. C; T_end: 220. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1363.	Formisano, Rigano, et al., 2007	30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (5 min) 2 0C/min -> 250 0C (15 min) 10 0C/min -> 270 0C
Capillary	SE-52	1369.	Tognolini, Barocelli, et al., 2006	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C (10min)
Capillary	HP-5MS	1369.	Sahin, Gulluce, et al., 2004	30. m/0.25 mm/0.25 μm, He; Program: 50C(3min) => 3C/min => 150C(10min) => 10C/min => 250C
Capillary	OV-1	1368.	Kökdil, 1998	50. m/0.32 mm/0.25 μm, He; Program: 1)50C(1min) => 4C/min => 180C => 2C/min => 250C(10min) 2)50C(1min) => 6C/min => 200C => 12C/min => 250C(5min)

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax FSC	1984.	Baser, Kirimer, et al., 1997	He, 60. C @ 10. min, 4. K/min, 240. C @ 10. min; Column length: 60. m; Column diameter: 0.25 mm

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax FSC	1983.	Kürkçüoglu, Hüsnü Can Baser, et al., 2006	60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C
Capillary	HP-Innowax	1983.	Baser, Demirci, et al., 2001	60. m/0.25 mm/0.25 μm, He; Program: 60 0C (10 min) 10 K/min -> 220 0C (10 min) 1K/min -> 240 0C

References

Go To: Top, Gas Chromatography, Notes

Juliani, Koroch, et al., 2002
Juliani, H.R., Jr.; Koroch, A.R.; Juliani, H.R.; Trippi, V.S.; Zygadlo, J.A., Intraespecific variation in leafoils of Lippia junelliana (mold.) tronc, Biochem. Syst. Ecol., 2002, 30, 2, 163-170, https://doi.org/10.1016/S0305-1978(01)00067-9 . [all data]

Kitic, Palic, et al., 2001
Kitic, D.; Palic, R.; Ristic, M.; Sojanovic, G.; Jovanovic, T., The volatile constituents of Calamintha sylvatica Bromf. subsp. sylvatica, Flavour Fragr. J., 2001, 16, 4, 257-258, https://doi.org/10.1002/ffj.995 . [all data]

Dwivedi, Khan, et al., 2004
Dwivedi, S.; Khan, M.; Srivastava, S.K.; Syamasunnder, K.V.; Srivastava, A., Essential oil composition of different accessions of Mentha × piperita L. grown on the northern plains of India, Flavour Fragr. J., 2004, 19, 5, 437-440, https://doi.org/10.1002/ffj.1333 . [all data]

Benzo, Gilardoni, et al., 2007
Benzo, M.; Gilardoni, G.; Gandini, C.; Caccialanza, G.; Finzi, P.V.; Vidari, G.; Abdo, S.; Layedra, P., Determination of the threshold odor concentration of main odorants in essential oils using gas chromatography-olfactometry incremental dilution technique, J. Chromatogr. A, 2007, 1150, 1-2, 131-135, https://doi.org/10.1016/j.chroma.2007.02.031 . [all data]

Flamini, Cioni, et al., 2007
Flamini, G.; Cioni, P.L.; Morelli, I.; Bader, A., Essential oils of the aerial parts of three Salvia species from Jordan: Salvia lanigera, S. spinosa and S. syriaca, Food Chem., 2007, 100, 2, 732-735, https://doi.org/10.1016/j.foodchem.2005.10.032 . [all data]

Vagionas, Ngassapa, et al., 2007
Vagionas, K.; Ngassapa, O.; Runyoro, D.; Graikou, K.; Gortzi, O.; Chinou, I., Chemical analysis of edible aromatic plants growing in Tanzania, Food Chem., 2007, 105, 4, 1711-1717, https://doi.org/10.1016/j.foodchem.2007.05.029 . [all data]

Javidnia, Miri, et al., 2004
Javidnia, K.; Miri, R.; Sadeghpour, H., Composition of the volatile oil of Achillea wilhelmsii C. Koch from Iran, DARU, 2004, 12, 2, 63-66, retrieved from http://www1.tums.ac.ir/daru/. [all data]

Sartoratto, Machado, et al., 2004
Sartoratto, A.; Machado, A.L.M.; Delarmelina, C.; Figueira, G.M.; Duarte, M.C.T.; Rehder, V.L.G., Composition and antimicrobial activity of essential oils from aromatic plants used in Brazil, Braz. J. Microbiol., 2004, 35, 4, 275-280, https://doi.org/10.1590/S1517-83822004000300001 . [all data]

Emilio Tomei, Manganelli, et al., 2003
Emilio Tomei, P.; Manganelli, R.E.U.; Flamini, G.; Cioni, P.L.; Morelli, I., Composition of the essential oil of Mentha microphylla from the Gennargentu Mountains (Sardinia, Italy), J. Agric. Food Chem., 2003, 51, 12, 3614-3617, https://doi.org/10.1021/jf026091w . [all data]

Javidnia, Miri, et al., 2003
Javidnia, K.; Miri, R.; Azarpira, A.; Tabaei, S.M.H., Composition of the essential oil of Stachys setifera C.A. Mey ssp. iranica growing in Iran, Flavour Fragr. J., 2003, 18, 4, 299-300, https://doi.org/10.1002/ffj.1165 . [all data]

Cavaleiro, Salgueiro, et al., 2002
Cavaleiro, C.; Salgueiro, L.R.; Antunes, T.; Sevinate-Pinto, I.; Barroso, J.G., Composition of the essential oil and micromorphology of trichomes of Teucrium salviastrum, an endemic species from Portugal, Flavour Fragr. J., 2002, 17, 4, 287-291, https://doi.org/10.1002/ffj.1068 . [all data]

Baldovini, Ristorcelli, et al., 2000
Baldovini, N.; Ristorcelli, D.; Tomi, F.; Casanova, J., Infraspecific variability of the essential oil of Calamintha nepeta from Corsica (France), Flavour Fragr. J., 2000, 15, 1, 50-54, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<50::AID-FFJ871>3.0.CO;2-F . [all data]

Sacchetti, Maietti, et al., 2005
Sacchetti, G.; Maietti, S.; Muzzoli, M.; Scaglianti, M.; Manfredini, S.; Radice, M.; Bruni, R., Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods, Food Chem., 2005, 91, 4, 621-632, https://doi.org/10.1016/j.foodchem.2004.06.031 . [all data]

Lorenzo, Paz, et al., 2002
Lorenzo, D.; Paz, D.; Dellacassa, E.; Davies, P.; Vila, R.; Cañigueral, S., Essential oils of Mentha pulegium and Mentha rotundifolia from Uruguay, Braz. Arch. Biol. Technol., 2002, 45, 4, 519-524, https://doi.org/10.1590/S1516-89132002000600016 . [all data]

Bertoli, Lepnardi, et al., 2011
Bertoli, A.; Lepnardi, M.; Krzyzanowska, J.; Oleszek, W.; Pistelli, L., Mentha longifolia in vitro cultures as safe source of flavouring ingradients, Acta Biochem. Polonica, 2011, 58, 4, 581-587. [all data]

Coelho, Grosso, et al., 2007
Coelho, J.A.; Grosso, C.; Pereira, A.P.; Burillo, J.; Urieta, J.S.; Figueiredo, A.C.; Barroso, J.G.; Mendes, R.L.; Palavra, A.M.F., Supercritical carbon dioxide extraction of volatiles from Satureja fruticosa Béguinot, Flavour Fragr. J., 2007, 22, 5, 438-442, https://doi.org/10.1002/ffj.1819 . [all data]

Setkova, Risticevic, et al., 2007
Setkova, L.; Risticevic, S.; Pawliszyn, J., Rapid headspace solid-phase microextraction-gas chromatographic?time-of-flight mass spectrometric method for qualitative profiling of ice wine volatile fraction II: Classification of Canadian and Czech ice wines using statistical evaluation of the data, J. Chromatogr. A, 2007, 1147, 2, 224-240, https://doi.org/10.1016/j.chroma.2007.02.052 . [all data]

Vagionas, Graikou, et al., 2007
Vagionas, K.; Graikou, K.; Ngassapa, O.; Runyoro, D.; Chinou, I., Composition and antimicrobial activity of the essential oils of three Satureja species growing in Tansania, Food Chem., 2007, 103, 2, 319-324, https://doi.org/10.1016/j.foodchem.2006.07.051 . [all data]

Yadegarinia, Gachkar, et al., 2006
Yadegarinia, D.; Gachkar, L.; Rezaei, M.B.; Taghizadeh, M.; Astaneh, S.A.; Rasooli, I., Biochemical activities of Iranian Mentha piperita L. and Myrtus communis L. essential oils, Phytochemistry, 2006, 67, 12, 1249-1255, https://doi.org/10.1016/j.phytochem.2006.04.025 . [all data]

Slavkovska, Couladis, et al., 2005
Slavkovska, V.; Couladis, M.; Bojovic, S.; Tzakou, O.; Pavlovic, M.; Lakusic, B.; Jancic, R., Essential oil and its systematic significance in species of Micromeria Bentham from Serbia Montenegro, Plant Systematics and Evolution, 2005, 255, 1-2, 1-15, https://doi.org/10.1007/s00606-005-0303-y . [all data]

De Pooter, De Buyck, et al., 1986
De Pooter, H.L.; De Buyck, L.F.; Schamp, N.M., The Volatiles of Calamintha Nepeta Subsp. Glandulosa, Phytochemistry, 1986, 25, 3, 691-694, https://doi.org/10.1016/0031-9422(86)88025-6 . [all data]

Formisano, Rigano, et al., 2007
Formisano, C.; Rigano, D.; Napolitano, F.; Senatore, F.; Arnold, N.A.; Piozzi, F.; Rosselli, S., Volatile constituents of Calamintha ariganifolia Boiss. growing wild in Lebanon, Natural Product Communications, 2007, 2, 12, 1253-1256. [all data]

Tognolini, Barocelli, et al., 2006
Tognolini, M.; Barocelli, E.; Ballabeni, V.; Bruni, R.; Bianchi, A.; Chiavarini, M.; Impicciatore, M., Comparative screening of plant essential oils: Phenylpropanoid moiety as basic core for antiplatelet activity, Life Sciences, 2006, 78, 13, 1419-1432, https://doi.org/10.1016/j.lfs.2005.07.020 . [all data]

Sahin, Gulluce, et al., 2004
Sahin, F.; Gulluce, M.; Daferera, D.; Sokmen, A.; Sokmen, M.; Polissiou, M.; Agar, G.; Ozer, H., Biological activities of the essential oils and methanol extract of Origanum vulgare ssp. vulgare in the Eastern Anatolia region of Turkey, Food Control, 2004, 15, 7, 549-557, https://doi.org/10.1016/j.foodcont.2003.08.009 . [all data]

Kökdil, 1998
Kökdil, G., Composition of the essential oil of Clinopodium vulgare L. ssp. arundanum (Boiss.) Nyman collected from two different localities in Turkey, Flavour Fragr. J., 1998, 13, 3, 170-172, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<170::AID-FFJ721>3.0.CO;2-H . [all data]

Baser, Kirimer, et al., 1997
Baser, K.H.C.; Kirimer, N.; Duman, H., Composition of the essential oil of Micromeria dolichodontha P. H. Davis, Flavour Fragr. J., 1997, 12, 4, 289-291, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<289::AID-FFJ640>3.0.CO;2-A . [all data]

Kürkçüoglu, Hüsnü Can Baser, et al., 2006
Kürkçüoglu, M.; Hüsnü Can Baser, K.; Iscan, G.; Malyer, H.; Kaynak, G., Composition and anticandidal activity of the essential oil of Chaerophyllum byzantinum Boiss., Flavour Fragr. J., 2006, 21, 1, 115-117, https://doi.org/10.1002/ffj.1539 . [all data]

Baser, Demirci, et al., 2001
Baser, K.H.C.; Demirci, B.; Tabanca, N.; Özek, T.; Gören, N., Composition of the essential oils of Tanacetum armenum (DC.) Schultz Bip., T. balsamita L., T. chiliophyllum (Fisch. Mey.) Schultz Bip. var. chiliophyllum and T. haradjani (Rech. fil.) Grierson and the enantiomeric distribution of camphor and carvone, Flavour Fragr. J., 2001, 16, 3, 195-200, https://doi.org/10.1002/ffj.977 . [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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