2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E)-
- Formula: C13H18O
- Molecular weight: 190.2814
- IUPAC Standard InChIKey: POIARNZEYGURDG-FNORWQNLSA-N
- 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:
- Stereoisomers:
- 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:
- Other data available:
- Options:
Van Den Dool and Kratz RI, 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
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-Wax | FFAP | DB-Wax | DB-Wax | FFAP |
Column length (m) | 30. | 30. | 30. | 30. | 30. |
Carrier gas | H2 | H2 | H2 | He | |
Substrate | |||||
Column diameter (mm) | 0.32 | 0.32 | 0.32 | 0.32 | 0.32 |
Phase thickness (μm) | 0.5 | 0.25 | 0.5 | 0.5 | 0.25 |
Program | 40C(5min) => 4C/min => 100C6C/min => 136C => 3C/min => 220C (10min) | 40C(2min) => 6C/min => 150C => 20C/min => 230C | 60C(3min) => 2C/min => 220C => 3C/min => 245C (20min) | 40C(5min) => 4C/min => 100C => 6C/min => 200C | 35C(2min) => 40C/min => 60C(2min) => 6C/min => 180C => 20C/min => 230C(10min) |
I | 1838. | 1815. | 1841. | 1841. | 1821. |
Reference | Escudero, Campo, et al., 2007 | Schuh and Schieberle, 2006 | Selli, Canbas, et al., 2006 | Campo, Ferreira, et al., 2005 | Fritsch and Schieberle, 2005 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | CP-Wax 52CB | Supelcowax-10 | DB-FFAP | Stabilwax | Stabilwax |
Column length (m) | 50. | 30. | 30. | 30. | 30. |
Carrier gas | He | He | He | He | |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.32 | 0.32 |
Phase thickness (μm) | 0.2 | 0.25 | 0.25 | 1. | 1. |
Program | 33C(1.5min) => 1.5C/min => 60C(4min) => 2C/min => 100C => 8C/min => 220C(15min) | 40C(2min) => 40C/min => 60(2min)C => 5C/min => 240C | 40C(2min) => 6C/min => 150C => 20C/min => 230C | 40C(2min) => 5C/min => 100C => 4C/min => 230C (10min) | 40C(2min) => 5C/min => 100C => 4C/min => 230C (10min) |
I | 1799. | 1823. | 1815. | 1819. | 1850. |
Reference | Kaack, Christensen, et al., 2005 | Majcher and Jelén, 2005 | Schuh and Schieberle, 2005 | Wang, Finn, et al., 2005 | Wang, Finn, et al., 2005 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-Wax | Stabilwax | Stabilwax | DB-Wax | FFAP |
Column length (m) | 60. | 30. | 30. | 30. | 25. |
Carrier gas | He | He | He | He | He |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.32 | 0.32 | 0.25 | 0.32 |
Phase thickness (μm) | 0.25 | 1. | 1. | 0.5 | 0.3 |
Program | 35C(0.7min) => 20C/min => 70C => 4C/min => 240C | 40C (2min) => 5C/min => 100C => 4C/min => 230C (10min) | 40C(2min) => 5C/min => 100C => 4C/min => 230C(10min) | 40C(2min) => 2C/min => 100C => 10C/min => 230C (5min) | 35C(2min) => 5C/min => 170C => 20C/min => 240C (10min) |
I | 1802. | 1852. | 1851. | 1837. | 1811. |
Reference | Ferrari, Lablanquie, et al., 2004 | Klesk, Qian, et al., 2004 | Klesk and Qian, 2003 | Klesk and Qian, 2003, 2 | Fuhrmann and Grosch, 2002 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | FFAP | FFAP | DB-FFAP | DB-Wax | FFAP |
Column length (m) | 30. | 30. | 30. | 30. | 30. |
Carrier gas | He | He | He | H2 | He |
Substrate | |||||
Column diameter (mm) | 0.32 | 0.32 | 0.25 | 0.25 | 0.32 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
Program | 35C (2min) => 60C/min => 50C (2min) => 6C/min => 240C (10min) | 35C (2min) => 60C/min => 50C (2min) => 6C/min => 240C (10min) | 35 0C (2 min) 40 K/min -> 60 0C (2 min) 6 K/min -> 230 0C | 60C (3min) => 2C/min => 220C => 5C/min => 250C (15min) | 40C(2min) => 40C/min => 60C(2min) => 6C/min => 240C(10min) |
I | 1806. | 1806. | 1805. | 1819. | 1806. |
Reference | Kirchhoff and Schieberle, 2002 | Kirchhoff and Schieberle, 2002 | Zehentbauer and Reineccius, 2002 | Boulanger and Crouzet, 2001 | Kirchhoff and Schieberle, 2001 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|
Active phase | FFAP | FFAP | FFAP | FFAP |
Column length (m) | 30. | 30. | 25. | 30. |
Carrier gas | He | He | He | He |
Substrate | ||||
Column diameter (mm) | 0.32 | 0.32 | 0.32 | 0.32 |
Phase thickness (μm) | 0.25 | 0.25 | 0.5 | 0.25 |
Program | 35C (2min) => 40C/min => 60C => 4C/min => 230C (10min) | 35C (2min) => 40C/min => 60C => 4C/min => 230C (10min) | 35C (2min) => 40C/min => 60C => 6C/min => 230C (10min) | 40C (2min) => 40C/min => 60C (2min) => 240C (10min) |
I | 1805. | 1805. | 1822. | 1806. |
Reference | Derail, Hofmann, et al., 1999 | Derail, Hofmann, et al., 1999 | Fickert and Schieberle, 1998 | Münch, Hofmann, et al., 1997 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Van Den Dool and Kratz RI, 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.
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]
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]
Selli, Canbas, et al., 2006
Selli, S.; Canbas, A.; Cabaroglu, T.; Erten, H.; Gunata, Z.,
Aroma components of cv. Muscat of Bornova wines and influence of skin contact treatment,
Food Chem., 2006, 94, 3, 319-326, https://doi.org/10.1016/j.foodchem.2004.11.019
. [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]
Kaack, Christensen, et al., 2005
Kaack, K.; Christensen, L.P.; Hughes, M.; Eder, R.,
The relationship between sensory quality and volatile compounds in raw juice processed from elderberries ( Sambucus nigra L.),
Eur. Food Res. Technol., 2005, 221, 3-4, 244-254, https://doi.org/10.1007/s00217-005-1141-4
. [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]
Schuh and Schieberle, 2005
Schuh, C.; Schieberle, P.,
Characterization of ( E, E, Z)-2,4,6-Nonatrienal as a character impact aroma compound of oat flakes,
J. Agric. Food Chem., 2005, 53, 22, 8699-8705, https://doi.org/10.1021/jf051601i
. [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]
Ferrari, Lablanquie, et al., 2004
Ferrari, G.; Lablanquie, O.; Cantagrel, R.; Ledauphin, J.; Payot, T.; Fournier, N.; Guichard, E.,
Determination of key odorant compounds in freshly distilled cognac using GC-O, GC-MS, and sensory evaluation,
J. Agric. Food Chem., 2004, 52, 18, 5670-5676, https://doi.org/10.1021/jf049512d
. [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]
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]
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]
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]
Notes
Go To: Top, Van Den Dool and Kratz RI, polar column, custom temperature program, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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