Longiverbenone

Formula: C₁₅H₂₂O
Molecular weight: 218.3346
IUPAC Standard InChI: InChI=1S/C15H22O/c1-9-8-10(16)12-13-11(9)15(12,4)7-5-6-14(13,2)3/h8,11-13H,5-7H2,1-4H3
IUPAC Standard InChIKey: KTPOZFYJWLGJGH-UHFFFAOYSA-N
CAS Registry Number: 64180-68-3
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
- Vulgarone A
- Mustakone
Other names: 2,6,6,11-Tetramethyltricyclo[5.4.0.02,8]undec-10-en-9-one; Vulgarone B; Longiverbenone (vulgarone B)
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
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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	HP-5MS	1627.	Couladis, Chinou, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1651.	Kundakovic, Fokialakis, et al., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	ZB-5	1647.	Simoniatto, Bonani, et al., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 50. C; T_end: 250. C
Capillary	HP-5MS	1670.	Saroglou, Dorizas, et al., 2006	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	DB-5	1641.	Sati and Mathela, 2005	30. m/0.25 mm/0.26 μm, He, 3. K/min; T_start: 60. C; T_end: 210. C
Capillary	DB-5	1649.	Nogueira, Bittrich, et al., 2001	30. m/0.25 mm/0.25 μm, H2, 3. K/min; T_start: 60. C; T_end: 240. 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	HP-5MS	1658.2	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax	2254.	Kundakovic, Fokialakis, et al., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1678.	Radulovic, Dordevic, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; T_start: 70. C
Capillary	Ultra 2	1648.	Byun and Shin, 2008	50. m/0.20 mm/0.11 μm, Helium, 60. C @ 5. min, 2. K/min, 230. C @ 30. min
Capillary	HP-5MS	1647.	Bozin, Mimicá-Dukic, et al., 2006	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	DB-5	1637.	Abreu and Noronha, 1997	He, 3. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 60. C; T_end: 250. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-5	1675.	Kilani, Ledauphin, et al., 2008	Program: not specified
Capillary	SPB-5	1694.	Kilani, Ledauphin, et al., 2008	Program: not specified
Capillary	SE-52	1651.	Tognolini, Barocelli, et al., 2006	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C (10min)
Capillary	BPX-5	1647.	Judzentiene and Mockute, 2005	30. m/0.25 mm/0.25 μm; Program: 60C(0.2min) => 3K/min => 186C => 10C/min => 240C (5min)
Capillary	CP Sil 8 CB	1647.	Mockute and Judzentiene, 2003	50. m/0.32 mm/0.25 μm, He; Program: 70C(5min) => 3C/min => 100C (1min) => 25C/min => 250C (10min)
Capillary	BP-1	1632.	Muselli, Bighelli, et al., 2000	50. m/0.22 mm/0.25 μm; Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	TC-Wax	2270.	Miyazawa, Yamafuji, et al., 2003	3. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_start: 80. C; T_end: 240. C

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax	2265.	Viljoen, van Vuuren, et al., 2003	60. m/0.25 mm/0.25 μm; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	BP-20	2222.	Muselli, Bighelli, et al., 2000	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Couladis, Chinou, et al., 2003
Couladis, M.; Chinou, I.B.; Tzakou, O.; Petrakis, P.V., Composition and antimicrobial activity of the essential oil of Hypericum rumeliacum subsp. apollinis (Boiss. Heldr.), Phytother. Res., 2003, 17, 2, 152-154, https://doi.org/10.1002/ptr.1093 . [all data]

Kundakovic, Fokialakis, et al., 2007
Kundakovic, T.; Fokialakis, N.; Kovacevic, N.; Chinou, I., Essential oil composition of Achillea lingulata and A. umbellata, Flavour Fragr. J., 2007, 22, 3, 184-187, https://doi.org/10.1002/ffj.1778 . [all data]

Simoniatto, Bonani, et al., 2007
Simoniatto, E.; Bonani, V.F.L.; Morel, A.F.; Poppi, N.R.; Raposo, J.L., Jr.; Stuker, C.Z.; Peruzzo, G.M.; Peres, M.T.L.P.; Hess, S.C., Chemical composition and evaluation of antibacterial and antioxidant activities of the essential oil of Croton urucurana Baillon (Euphorbiaceae) stem bark, J. Braz. Chem., 2007, 18, 5, 879-885, https://doi.org/10.1590/S0103-50532007000500002 . [all data]

Saroglou, Dorizas, et al., 2006
Saroglou, V.; Dorizas, N.; Kypriotakis, Z.; Skaltsa, H.D., Analysis of the essential oil composition of eight Anthemis species from Greece, J. Chromatogr. A, 2006, 1104, 1-2, 313-322, https://doi.org/10.1016/j.chroma.2005.11.087 . [all data]

Sati and Mathela, 2005
Sati, S.; Mathela, C.S., Essential oil composition of Valeriana hardwickii var. arnottiana from the Himalayas, Flavour Fragr. J., 2005, 20, 3, 299-301, https://doi.org/10.1002/ffj.1415 . [all data]

Nogueira, Bittrich, et al., 2001
Nogueira, P.C.L.; Bittrich, V.; Shepherd, G.J.; Lopes, A.V.; Marsaioli, A.J., The ecological and taxonomic importance of flower volatiles of Clusia species (Guttiferae), Phytochemistry, 2001, 56, 5, 443-452, https://doi.org/10.1016/S0031-9422(00)00213-2 . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Radulovic, Dordevic, et al., 2010
Radulovic, N.; Dordevic, N.; Markovic, M.; Palic, R., Volatile constituents of Glechoma Hirsuta Waldst. Kit. and G. Hederacea L. (Lamiaceae), Bull. Chem. Soc. Ethiop., 2010, 24, 1, 67-76, https://doi.org/10.4314/bcse.v24i1.52962 . [all data]

Byun and Shin, 2008
Byun, Y.; Shin, S., Analysis of compounds and activity of essential oil from Chrysanthemum zawadskii var. latilobum and C. indicum agaunst antibiotic-resistant pathogenic bacteria, Nat. Prod. Sci., 2008, 14, 2, 138-142. [all data]

Bozin, Mimicá-Dukic, et al., 2006
Bozin, B.; Mimicá-Dukic, N.; Simin, N.; Anackov, G., Characterization of the volatile composition of essential oils of some lamiaceae spices and the antimicrobial and antioxidant activities of the entire oils, J. Agric. Food Chem., 2006, 54, 5, 1822-1828, https://doi.org/10.1021/jf051922u . [all data]

Abreu and Noronha, 1997
Abreu, P.M.; Noronha, R.G., Volatile constituents of the rhizomes of Aframomum alboviolaceum (Ridley) K. Schum. from Guinea-Bissau, Flavour Fragr. J., 1997, 12, 2, 79-83, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<79::AID-FFJ617>3.0.CO;2-7 . [all data]

Kilani, Ledauphin, et al., 2008
Kilani, S.; Ledauphin, J.; Bouhlel, I.; Ben Sghaier, M.; Boubaker, J.; Skandrani, I.; Mosrati, R.; Ghedira, K.; Barillier, D.; Chekir-Ghedira, L., Comparative study of Cyperus rotundus essential oil by a modified GC/MS analysis method. Evaluation of its antioxidantt, cytotoxic, and apoptoic effects, Chem. Biodiversity, 2008, 5, 5, 729-742, https://doi.org/10.1002/cbdv.200890069 . [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]

Judzentiene and Mockute, 2005
Judzentiene, A.; Mockute, D., The inflorescence and leaf essential oils of Tanacetum vulgare L. var. vulgare growing wild in Lithuania, Biochem. Syst. Ecol., 2005, 33, 5, 487-498, https://doi.org/10.1016/j.bse.2004.11.003 . [all data]

Mockute and Judzentiene, 2003
Mockute, D.; Judzentiene, A., The myrtenol chemotype of essential oil of Tanacetum vulgare L. var. vulgare (tansy) growing wild in the Vilnius region, Chemija, 2003, 14, 2, 103-107. [all data]

Muselli, Bighelli, et al., 2000
Muselli, A.; Bighelli, A.; Hoi, T.M.; Thao, N.T.P.; Thai, T.H.; Casanova, J., Dihydroperillaldehydes from Enhydra fluctuans Lour. essential oil, Flavour Fragr. J., 2000, 15, 5, 299-302, https://doi.org/10.1002/1099-1026(200009/10)15:5<299::AID-FFJ911>3.0.CO;2-I . [all data]

Miyazawa, Yamafuji, et al., 2003
Miyazawa, M.; Yamafuji, C.; Kurose, K.; Ishikawa, Y., Volatile components of the rhizomes of Cirsium japonicum DC, Flavour Fragr. J., 2003, 18, 1, 15-17, https://doi.org/10.1002/ffj.1135 . [all data]

Viljoen, van Vuuren, et al., 2003
Viljoen, A.; van Vuuren, S.; Ernst, E.; Klepser, M.; Demirci, B.; Baser, H.; van Wyk, B.-E., Osmitopsis asteriscoides (Asteraceae)-the antimicrobial activity and essential oil composition of a Cape-Dutch remedy, J. Ethnopharmacol., 2003, 88, 2-3, 137-143, https://doi.org/10.1016/S0378-8741(03)00191-0 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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