2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E)-

• Formula: C₁₃H₁₈O
• Molecular weight: 190.2814
• IUPAC Standard InChI: InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ Copy

  
• IUPAC Standard InChIKey: POIARNZEYGURDG-FNORWQNLSA-N Copy
• CAS Registry Number: 23726-93-4
• 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.
• Species with the same structure:
  • 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-
  • Damascenone A
  • (E)-β-Damascenone
• Stereoisomers:
  • (Z)-β-Damascenone
  • (Z)-β-Damascenone
  • cis-β-Damascenone
• Other names: β-Damascenone; trans-β-Damascenone; Damascenone; Damascenone, trans-; 2,6,6-Trimethyl-1-trans-crotonoyl-1,3-cyclohexadiene; (2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; β-(E)-Damascenone; 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, trans-; (2 E)-1-(2,6,6-trimethylcyclohexane-1,3-dien-1-yl)but-2-en-1-one; (E)-β-Damascenone; trans-Damascenone; 36649-63-5; 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one (β-damascenone); (2 E)-1-(2,6,6-trimethylcyclohexane-1,3-dien-1-yl)but-2-en-1-one (β-damascenone); (E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
• Information on this page:
  • Van Den Dool and Kratz RI, non-polar column, custom temperature program
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Options:
  • Switch to calorie-based units

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

Go To: Top, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

References

Go To: Top, Van Den Dool and Kratz RI, non-polar column, custom temperature program, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Dharmawan, Kasapis, et al., 2007
Dharmawan, J.; Kasapis, S.; Curran, P.; Johnson, J.R., Characterization of volatile compounds in selected citrus fruits from Asia. Part I: freshly-squeezed juice, Flavour Fragr. J., 2007, 22, 3, 228-232, https://doi.org/10.1002/ffj.1790 . [all data]

Escudero, Campo, et al., 2007
Escudero, A.; Campo, E.; Fariña, L.; Cacho, J.; Ferreira, V., Analytical Characterization of the Aroma of Five Premium Red Wines. Insights into the Role of Odor Families and the Concept of Fruitiness of Wines, J. Agric. Food Chem., 2007, 55, 11, 4501-4510, https://doi.org/10.1021/jf0636418 . [all data]

Eyres, Marriott, et al., 2007
Eyres, G.T.; Marriott, P.J.; Dufour, J.-P., Comparison of Odor-Active Compounds in the Spicy Fraction of Hop (Humulus lupulus L.) Essential Oil from Four Different Varieties, J. Agric. Food Chem., 2007, 55, 15, 6252-6261, https://doi.org/10.1021/jf070739t . [all data]

Pérez, Navarro, et al., 2007
Pérez, R.A.; Navarro, T.; de Lorenzo, C., HS-SPME analysis of the volatile compounds from spices as a source of flavour in 'Campo Real' table olive preparations, Flavour Fragr. J., 2007, 22, 4, 265-273, https://doi.org/10.1002/ffj.1791 . [all data]

Sampaio and Nogueira, 2006
Sampaio, T.S.; Nogueira, P.C.L., Volatile components of mangaba fruit (Hancornia speciosa Gomes) at three stages of maturity, Food Chem., 2006, 95, 4, 606-610, https://doi.org/10.1016/j.foodchem.2005.01.038 . [all data]

Schuh and Schieberle, 2006
Schuh, C.; Schieberle, P., Characterization of the Key Aroma Compounds in the Beverage Prepared from Darjeeling Black Tea: Quantitative Differences between Tea Leaves and Infusion, J. Agric. Food Chem., 2006, 54, 3, 916-924, https://doi.org/10.1021/jf052495n . [all data]

Bonaiti, Irlinger, et al., 2005
Bonaiti, C.; Irlinger, F.; Spinnler, H.E.; Engel, E., An iterative sensory procedure to select odor-active associations in complex consortia of microorganisms: application to the construction of a cheese model, J. Dairy Sci., 2005, 88, 5, 1671-1684, https://doi.org/10.3168/jds.S0022-0302(05)72839-3 . [all data]

Campo, Ferreira, et al., 2005
Campo, E.; Ferreira, V.; Escudero, A.; Cacho, J., Prediction of the wine sensory properties related to grape variety from dynamic-headspace gas chromatography-olfactometry data, J. Agric. Food Chem., 2005, 53, 14, 5682-5690, https://doi.org/10.1021/jf047870a . [all data]

Fritsch and Schieberle, 2005
Fritsch, H.T.; Schieberle, P., Identification based on quantitative measurements and aroma recombination of the character impact odorants in a Bavarian Pilsner-type beer, J. Agric. Food Chem., 2005, 53, 19, 7544-7551, https://doi.org/10.1021/jf051167k . [all data]

Majcher and Jelén, 2005
Majcher, M.A.; Jelén, H.H., Identification of potent odorants formed during the preparation of extruded potato snacks, J. Agric. Food Chem., 2005, 53, 16, 6432-6437, https://doi.org/10.1021/jf050412x . [all data]

Wang, Finn, et al., 2005
Wang, Y.; Finn, C.; Qian, M.C., Impact of Growing Environment on Chickasaw Blackberry ( Rubus L.) Aroma Evaluated by Gas Chromatography Olfactometry Dilution Analysis, J. Agric. Food Chem., 2005, 53, 9, 3563-3571, https://doi.org/10.1021/jf048102m . [all data]

Klesk, Qian, et al., 2004
Klesk, K.; Qian, M.; Martin, R.R., Aroma extract dilution analysis of cv. meeker (Rubus idaeus L.) red raspberries from Oregon and Washington, J. Agric. Food Chem., 2004, 52, 16, 5155-5161, https://doi.org/10.1021/jf0498721 . [all data]

Klesk and Qian, 2003
Klesk, K.; Qian, M., Aroma extract dilution analysis of Cv. Marion (Rubus spp. hyb) and Cv. Evergreen (R. Iaciniatus L.) blackberries, J. Agric. Food Chem., 2003, 51, 11, 3436-3441, https://doi.org/10.1021/jf0262209 . [all data]

Klesk and Qian, 2003, 2
Klesk, K.; Qian, M., Preliminary aroma comparison of Marion (Rubus spp. hyb) and Evergreen (R. laciniatus L.) blackberries by dynamic headspace/OSME technique, J. Food Sci., 2003, 68, 2, 697-700, https://doi.org/10.1111/j.1365-2621.2003.tb05734.x . [all data]

Fuhrmann and Grosch, 2002
Fuhrmann, E.; Grosch, W., Character impact odorants of the apple cultivars Elstar and Cox Orange, Nahrung/Food, 2002, 46, 3, 187-193, https://doi.org/10.1002/1521-3803(20020501)46:3<187::AID-FOOD187>3.0.CO;2-5 . [all data]

Kirchhoff and Schieberle, 2002
Kirchhoff, E.; Schieberle, P., Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays, J. Agric. Food Chem., 2002, 50, 19, 5378-5385, https://doi.org/10.1021/jf020236h . [all data]

Zehentbauer and Reineccius, 2002
Zehentbauer, G.; Reineccius, G.A., Determination of key aroma components of cheddar cheese using dynamic headspace dilution assay, Flavour Fragr. J., 2002, 17, 4, 300-305, https://doi.org/10.1002/ffj.1102 . [all data]

Boulanger and Crouzet, 2001
Boulanger, R.; Crouzet, J., Identification of the aroma components of acerola (Malphigia glabra L.): free and bound flavor compounds, Food Chem., 2001, 74, 2, 209-216, https://doi.org/10.1016/S0308-8146(01)00128-5 . [all data]

Duckham, Dodson, et al., 2001
Duckham, S.C.; Dodson, A.T.; Bakker, J.; Ames, J.M., Volatile flavour components of baked potato flesh. A comparison of eleven potato cultivars, Nahrung/Food, 2001, 45, 5, 317-323, https://doi.org/10.1002/1521-3803(20011001)45:5<317::AID-FOOD317>3.0.CO;2-4 . [all data]

Kirchhoff and Schieberle, 2001
Kirchhoff, E.; Schieberle, P., Determination of key aroma compounds in the crumb of a three-stage sourdough rye bread by stable isotope dilution assays and sensory studies, J. Agric. Food Chem., 2001, 49, 9, 4304-4311, https://doi.org/10.1021/jf010376b . [all data]

Derail, Hofmann, et al., 1999
Derail, C.; Hofmann, T.; Schieberle, P., Differences in key odorants of handmade juice of yellow-flesh peaches (Prunus persica L.) induced by the workup procedure, J. Agric. Food Chem., 1999, 47, 11, 4742-4745, https://doi.org/10.1021/jf990459g . [all data]

Mutti and Grosch, 1999
Mutti, B.; Grosch, W., Potent odorants of boiled potatoes, Nahrung, 1999, 43, 5, 302-306, https://doi.org/10.1002/(SICI)1521-3803(19991001)43:5<302::AID-FOOD302>3.0.CO;2-8 . [all data]

Fickert and Schieberle, 1998
Fickert, B.; Schieberle, P., Identification of the key odorants in barley malt (caramalt) using GC/MS techniques and odour dilution analyses, Nahrung, 1998, 42, 6, 371-375, https://doi.org/10.1002/(SICI)1521-3803(199812)42:06<371::AID-FOOD371>3.0.CO;2-V . [all data]

Kubícková and Grosch, 1997
Kubícková, J.; Grosch, W., Evaluation of potent odorants of camembert cheese by dilution and concentration techniques, Int. Dairy J., 1997, 7, 1, 65-70, https://doi.org/10.1016/S0958-6946(96)00044-1 . [all data]

Milo and Reineccius, 1997
Milo, C.; Reineccius, G.A., Identification and quantification of potent odorants in regular-fat and low-fat mild cheddar cheese, J. Agric. Food Chem., 1997, 45, 9, 3590-3594, https://doi.org/10.1021/jf970152m . [all data]

Münch, Hofmann, et al., 1997
Münch, P.; Hofmann, T.; Schieberle, P., Comparison of key odorants generated by thermal treatment of commercial and self-prepared yeast extracts: influence of the amino acid composition on odorant formation, J. Agric. Food Chem., 1997, 45, 4, 1338-1344, https://doi.org/10.1021/jf960658p . [all data]

Sing, Smadja, et al., 1992
Sing, A.S.C.; Smadja, J.; Brevard, H.; Maignial, L.; Chaintreau, A.; Marion, J.-P., Volatile constituents of faham (Jumellea fragrans (Thou.) Schltr.), J. Agric. Food Chem., 1992, 40, 4, 642-646, https://doi.org/10.1021/jf00016a024 . [all data]

Notes

Go To: Top, Van Den Dool and Kratz RI, non-polar column, custom temperature program, References

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