Furaneol
- Formula: C6H8O3
- Molecular weight: 128.1259
- IUPAC Standard InChIKey: INAXVXBDKKUCGI-UHFFFAOYSA-N
- CAS Registry Number: 3658-77-3
- 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. - Other names: 2,5-Dimethyl-4-hydroxy-3(2H)-furanone; 3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-; 3(2H)-Furanone, 2,5-dimethyl-4-hydroxy-; Alletone; COE 536; FEMA 3174; 4-Hydroxy-2,5-dimethyl-3(2H)furanone; Pineapple ketone; 2,3-Dihydro-4-hydroxy-2,5-dimethyl-3-furanone; 2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one; 2,5-Dimethyl-4-hydroxy-(2H)-furan-3-one; 4-Hydroxy-2,5-dimethylfuran-3(2H)-one; 2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuran; 2,5-dimethyl-4-hydroxy-3(2H)-furanone (Furaneol); 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol); 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF); 4-hydroxy-2,5-dimethylfuran-3( 2H)-one (Furaneol); 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one (furaneol); 2,5-Dimethyl-4-hydroxy-3(2H)-fuiranone; 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF); 2,5-Dimethyl-4(1H)-hydroxy-3(2H)-furanone; 2,5-dimethyl-4-hydroxy-(2H)-furan-3-one (furaneol); 4-Hydroxy-2,5-dimethyl-3-furanone; hydroxy-2,5-dimethyl-3(2H)-4-furanone (Furaneol); 4-hydroxy-2,5-dimethylfuran-2(3H)-one
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Normal alkane 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
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | CP-Sil 5 CB | SLB-5 MS | SLB-5 MS | CP Sil-5 CB | DB-5 |
Column length (m) | 50. | 30. | 30. | 50. | 30. |
Carrier gas | Nitrogen | Helium | Helium | Nitrogen | Hydrogen |
Substrate | |||||
Column diameter (mm) | 0.32 | 0.25 | 0.25 | 0.32 | 0.32 |
Phase thickness (μm) | 1.20 | 0.25 | 0.25 | 1.20 | 0.50 |
Program | 36 0C 20 0C/min -> 85 0C 1 0C/min -> 145 0C 3 0C/min -> 250 0C | not specified | not specified | 36 0C 20 0C/min -> 85 0C 1 0C/min -> 145 0C 3 0C/min -> 250 0C | 40 0C (5 min) 4 0C/min -> 100 0C 6 0C/min -> 220 0C (20 min) |
I | 1025. | 1059. | 1061. | 1025. | 1096. |
Reference | Collin, Nizet, et al., 2012 | Mondello, 2012 | Mondello, 2012 | Bailly and Collin, 2010 | San-Juan, Petka, et al., 2010 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | CP-Sil 5 CB | SE-54 | RTX-5 MS | RTX-5 MS | DB-5 |
Column length (m) | 50. | 30. | 30. | 30. | 30. |
Carrier gas | Nitrogen | Helium | Helium | Helium | Hydrogen |
Substrate | |||||
Column diameter (mm) | 0.32 | 0.32 | 0.25 | 0.25 | 0.32 |
Phase thickness (μm) | 1.20 | 0.25 | 0.25 | 0.25 | 0.50 |
Program | 36 0C 20 0C/min -> 85 0C 1 0C -> 145 0C 3 0C/min -> 250 0C | 35 0C (2 min) 10 0C/min -> 50 0C (2 min) 6 0C/min -> 250 0C | 50 0C (5 min) 2 0C/min -> 100 0C (5 min) 5 0C/min -> 300 0C | not specified | 40 0C 2 0C/min -> 12 0C/min -> 105 0C 6 0C/min -> 220 0C (20 min) |
I | 1025. | 1070. | 1108. | 1090. | 1064. |
Reference | Bailly, Jerkovic, et al., 2009 | Christlbauer and Schieberle, 2009 | Mebazaa, Mahmoudi, et al., 2009 | Mebazaa, Mahmoudi, et al., 2009 | Prat, Trias, et al., 2009 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | ZB-5 | HP-5 MS | DB-5 | HP-5MS | SE-54 |
Column length (m) | 30. | 30. | 30. | 30. | 30. |
Carrier gas | Helium | Helium | He | ||
Substrate | |||||
Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.25 | 0.32 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
Program | 45 0C 3 0C/min -> 230 0C (10 min) 10 0C/min -> 270 0C (21 min) | 50 0C (2 min) 20 0C/min -> 80 0C (1 min) 20 0C -> 100 0C (1 min) 30 0C/min -> 230 0C (2 min) | 40C(2min) => 40C/min => 60C(2min) => 6C/min => 180C => 15C/min => 230C(10min) | 50C(2min) => 20C/min => 80C (1min) => 20C/min => 100C(1min) => 30C/min => 230C(3min) | 35C(2min) => 40C/min => 60C(2min) => 6C/min => 180C => 10C/min => 230C(10min) |
I | 1083. | 1060. | 1070. | 1060. | 1070. |
Reference | de Simon, Estruelas, et al., 2009 | Wan Aida, Ho, et al., 2008 | Buettner, 2007 | Ho, Wan Aida, et al., 2007 | Lasekan, Buettner, et al., 2007 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | CP-Sil 5 CB | CP Sil 5 CB | DB-5 | SE-54 | MFE-73 |
Column length (m) | 50. | 50. | 30. | 30. | |
Carrier gas | Helium | He | Helium | He | |
Substrate | |||||
Column diameter (mm) | 0.32 | 0.32 | 0.32 | 0.32 | |
Phase thickness (μm) | 1.20 | 1.2 | 0.25 | 0.25 | |
Program | 36 0C 20 0C/min -> 85 0C 1 0C/min -> 1345 0C 3 0C/min -> 250 0C | 36C => 20C/min => 85C => 1C/min => 145C => 3C/min => 250C | 40 0C (2 min) 40 0C/min -> 60 0C (2 min) 6 0C/min -> 180 0C 10 0C/min -> 240 0C (5 min) | 40C(2min) => 40C/min => 50C(2min) => 6C/min => 180C => 15C/min => 230C (10min) | not specified |
I | 1025. | 1025. | 1063. | 1062. | 1096. |
Reference | Bailly, Jerkovic, et al., 2006 | Bailly, Jerkovic, et al., 2006, 2 | Tokitomo, Steihaus, et al., 2005 | Buettner, 2004 | Escudero, Gogorza, et al., 2004 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | HP-5MS | DB-5 | CP Sil 5 CB | MFE-73 | HP-5 |
Column length (m) | 30. | 30. | 50. | 30. | |
Carrier gas | He | H2 | |||
Substrate | |||||
Column diameter (mm) | 0.25 | 0.32 | 0.32 | 0.25 | |
Phase thickness (μm) | 0.25 | 1. | 1.2 | 0.25 | |
Program | 40C(5min) => 2C/min => 120C => 10C/min => 210C (30min) | 35C(4min) => 2C/min => 130C => 4C/min => 250C | 36C => 20C/min => 85C => 1C/min => 145C=3C/min => 250C(30min) | not specified | not specified |
I | 1098. | 1090. | 1023. | 1096. | 1090. |
Reference | Martí, Mestres, et al., 2003 | Qian and Reineccius, 2003 | Counet, Callemien, et al., 2002 | Ferreira, Ortín, et al., 2002 | Jordán, Goodner, et al., 2002 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | MFE-73 | MFE-73 | CP Sil 5 CB | HP-1 | DB-5 |
Column length (m) | 30. | 30. | 50. | 50. | 30. |
Carrier gas | H2 | H2 | N2 | Helium | |
Substrate | |||||
Column diameter (mm) | 0.32 | 0.32 | 0.32 | 0.32 | 0.25 |
Phase thickness (μm) | 0.1 | 0.1 | 1.2 | 0.52 | 0.25 |
Program | 40C(5min) => 2C/min => 120C => 10C/min => 210C(30min) | 40 C (5min) => 2C/min => 120C => 10 C/min => 210 C (30min) | 36C => 20C/min => 120C(20min) => 2C/min => 250C(30min) | 40C => 2C/min => 130C => 4C/min => 250C | 35 0C (2 min) 40 0C/min -> 50 0C (1 min) 6 0C/min -> 180 0C 10 0C/min -> 240 0C (10 min) |
I | 1096. | 1096. | 1024. | 1028. | 1056. |
Reference | Aznar, López, et al., 2001 | Ferreira, Aznar, et al., 2001 | Lermusieau, Bulens, et al., 2001 | Teai, Claude-Lafontaine, et al., 2001 | Lin, Fay, et al., 2000 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-5 | DB-5 | SE-54 | SE-54 | DB-5 |
Column length (m) | 30. | 30. | 30. | 30. | 30. |
Carrier gas | He | He | He | ||
Substrate | |||||
Column diameter (mm) | 0.32 | 0.32 | 0.32 | 0.32 | 0.32 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | ||
Program | 35C(1min) => 40C/min => 60C (1min) => 6C/min => 230C | 35C (1min) => 40C/min => 60C (1min) => 6C/min => 250C (10min) | 35C => 40C/min => 60C (1min) => 6C/min => 250C | 35C (2min) => 40C/min => 60C (2min) => 6C/min => 180C => 10C/min => 240C | not specified |
I | 1066. | 1061. | 1065. | 1070. | 1070. |
Reference | Matsui, Guth, et al., 1998 | Guth, 1997 | Lizárraga-Guerra, Guth, et al., 1997 | Schermann and Schieberle, 1997 | Schieberle, 1996 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary |
---|---|---|---|
Active phase | SE-54 | SE-54 | SE-54 |
Column length (m) | |||
Carrier gas | |||
Substrate | |||
Column diameter (mm) | |||
Phase thickness (μm) | |||
Program | 0C (2min) => 6C/min => 50C (2min) => 6C/min => 230 C (10min) | not specified | not specified |
I | 1061. | 1061. | 1065. |
Reference | Guth and Grosch, 1994 | Guth and Grosch, 1993 | Blank, Sen, et al., 1992 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Normal alkane 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.
Collin, Nizet, et al., 2012
Collin, S.; Nizet, S.; Bouuaert, T.C.; Despartures, P.-M.,
MAin odorants in Jura Flor-Sherry wines. Relative contributions of sotolon, abhexon, and theaspirane-derived compounds,
J. Agr. Food Chem., 2012, 60, 1, 380-381, https://doi.org/10.1021/jf203832c
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Mondello, 2012
Mondello, L.,
HS-SPME-GCxGC-MS analysis of Yerba Mate (Ilex paraguariensis)
in Shimadzu GC-GC application compendium of comprehensive 2D GC, Vol. 1-5, Shimadzu Corp., 2012, 1-29. [all data]
Bailly and Collin, 2010
Bailly, S.; Collin, S.,
Fate of polyunsaturated thiols in sauternes wines through ageing
in Expression of Multidisciplinary Flavour Sci., Blank, I.; Wust, M.; Yertzian, C., ed(s)., Zhaw Ed., 2010, 227-230, retrieved from https://home.zhaw.ch/tildayere/pdf/Teil58-Expression of Multidisciplinary.pdf. [all data]
San-Juan, Petka, et al., 2010
San-Juan, F.; Petka, J.; Cacho, J.; Ferreira, V.; Escudero, A.,
Producing headspace extracts for the gas chromatography - olphactometric evaluation of wine aroma,
Food Chemistry, 2010, 123, 1, 188-195, https://doi.org/10.1016/j.foodchem.2010.03.129
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Bailly, Jerkovic, et al., 2009
Bailly, S.; Jerkovic, V.; Meuree, A.; Timmermans, A.; Collin, S.,
Fate of key odorants in Sauternes wines through aging,
J. Agric. Food Chem., 2009, 57, 18, 8557-8563, https://doi.org/10.1021/jf901429d
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Christlbauer and Schieberle, 2009
Christlbauer, M.; Schieberle, P.,
Characterization of the key aroma compounds in beef and pork vegetable gravies a la chef by application of the aroma extract dilution analysis,
J. Agric. Food Chem., 2009, 57, 19, 9114-9112, https://doi.org/10.1021/jf9023189
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Mebazaa, Mahmoudi, et al., 2009
Mebazaa, R.; Mahmoudi, A.; Fouchet, M.; Dos Santos, M.; Kamissoko, F.; Nafti, A.; Ben Cheikh, R.; Rega, B.; Camel, V.,
Characterization of volatile compounds in Tunisian fenugreek seeds,
Food Chem., 2009, 115, 4, 1326-1336, https://doi.org/10.1016/j.foodchem.2009.01.066
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Prat, Trias, et al., 2009
Prat, C.; Trias, R.; Cullere, L.; Escudero, A.; Antico, E.; BAneras, L.,
Off-odor compounds produced in cork by isolated bacteria and fungi: a gas chromatography - mass spectrometry and gas chromatography - olfactometry study,
J. Agric. Food Chem., 2009, 57, 16, 7473-7479, https://doi.org/10.1021/jf900723s
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de Simon, Estruelas, et al., 2009
de Simon, B.F.; Estruelas, E.; Munoz, A.M.; Cadahia, E.; Sanz, M.,
Volatile compounds in acacia, chestnut, cherry, ash, and oak woods, with a view to their use in cooperage,
J. Agric. Food Chem., 2009, 57, 8, 3217-3227, https://doi.org/10.1021/jf803463h
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Wan Aida, Ho, et al., 2008
Wan Aida, W.M.; Ho, C.W.; Maskat, M.Y.; Osman, H.,
Relating descriptive sensory analysis to gas chromatography / mass spectrometry of palm sugars using partial least squares regression,
ASEAN Food J., 2008, 15, 1, 35-45. [all data]
Buettner, 2007
Buettner, A.,
A selective and sensitive approach to characterize odour-active and volatile constituents in small-scale human milk samples,
Flavour Fragr. J., 2007, 22, 6, 465-473, https://doi.org/10.1002/ffj.1822
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Ho, Wan Aida, et al., 2007
Ho, C.W.; Wan Aida, W.M.; Maskat, M.Y.; Osman, H.,
Changes in volatile compounds of palm sap (Arenga pinnata) during the heating process for production of palm sugar,
Food Chem., 2007, 102, 4, 1156-1162, https://doi.org/10.1016/j.foodchem.2006.07.004
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Lasekan, Buettner, et al., 2007
Lasekan, O.; Buettner, A.; Christlbauer, M.,
Investigation of important odorants of palm wine (Elaeis guineensis),
Food Chem., 2007, 105, 1, 15-23, https://doi.org/10.1016/j.foodchem.2006.12.052
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Bailly, Jerkovic, et al., 2006
Bailly, S.; Jerkovic, V.; Collin, S.,
Identification of key-odorants in Sauternes wines, Identification of key-odorants in Sauternes wines, 5th International Terroir Congress, 2006, 4. [all data]
Bailly, Jerkovic, et al., 2006, 2
Bailly, S.; Jerkovic, V.; Marchand-Brynaert, J.; Collin, S.,
Aroma Extraction Dilution Analysis of Sauternes Wines. Key Role of Polyfunctional Thiols,
J. Agric. Food Chem., 2006, 54, 19, 7227-7234, https://doi.org/10.1021/jf060814k
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Tokitomo, Steihaus, et al., 2005
Tokitomo, Y.; Steihaus, M.; Buttner, A.; Schieberle, P.,
Odor-Active Constituents in Fresh Pineapple (ananas comosus [L.] Merr.) by Quamtitative and Sensory Evaluations,
Biosci. Biotechnol, Biochem,, 2005, 69, 7, 1323-1330, https://doi.org/10.1271/bbb.69.1323
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Buettner, 2004
Buettner, A.,
Investigation of potent odorants and afterodor development in two chardonnay wines using the Buccal Odor Screening System (BOSS),
J. Agric. Food Chem., 2004, 52, 8, 2339-2346, https://doi.org/10.1021/jf035322b
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Escudero, Gogorza, et al., 2004
Escudero, A.; Gogorza, B.; Melús, M.A.; Ortín, N.; Cacho, J.; Ferreira, V.,
Characterization of the aroma of a wine from Maccabeo. Key role played by compounds with low odor activity values,
J. Agric. Food Chem., 2004, 52, 11, 3516-3524, https://doi.org/10.1021/jf035341l
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Martí, Mestres, et al., 2003
Martí, M.P.; Mestres, M.; Sala, C.; Busto, O.; Guasch, J.,
Solid-phase microextraction and gas chromatography olfactometry analysis of successively diluted samples. A new approach of the aroma extract dilution analysis applied to the characterization of wine aroma,
J. Agric. Food Chem., 2003, 51, 27, 7861-7865, https://doi.org/10.1021/jf0345604
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Qian and Reineccius, 2003
Qian, M.; Reineccius, G.,
Potent aroma compounds in Parmigiano Reggiano cheese studied using a dynamic headspace (purge-trap) method,
Flavour Fragr. J., 2003, 18, 3, 252-259, https://doi.org/10.1002/ffj.1194
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Counet, Callemien, et al., 2002
Counet, C.; Callemien, D.; Ouwerx, C.; Collin, S.,
Use of gas chromatography-olfactometry to identify key odorant compounds in dark chocolate. Comparison of samples before and after conching,
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Ferreira, Ortín, et al., 2002
Ferreira, V.; Ortín, N.; Escudero, A.; López, R.; Cacho, J.,
Chemical characterization of the aroma of grenache Rosé wines: aroma extract dilution analysis, quantitative determination, and sensory reconstitution studies,
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Jordán, Goodner, et al., 2002
Jordán, M.J.; Goodner, K.L.; Shaw, P.E.,
Characterization of the aromatic profile in aqueous essence and fruit juice of yellow passion fruit (Passiflora edulis Sims F. Flavicarpa degner) by GC-MS and GC/O,
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Aznar, López, et al., 2001
Aznar, M.; López, R.; Cacho, J.F.; Ferreira, V.,
Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions,
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Ferreira, Aznar, et al., 2001
Ferreira, V.; Aznar, M.; López, R.; Cacho, J.,
Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Differences in the odor profiles of four high-quality spanish aged red wines,
J. Agric. Food Chem., 2001, 49, 10, 4818-4824, https://doi.org/10.1021/jf010283u
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Lermusieau, Bulens, et al., 2001
Lermusieau, G.; Bulens, M.; Collin, S.,
Use of GC-olfactometry to identify the hop aromatic compounds in beer,
J. Agric. Food Chem., 2001, 49, 8, 3867-3874, https://doi.org/10.1021/jf0101509
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Teai, Claude-Lafontaine, et al., 2001
Teai, T.; Claude-Lafontaine, A.; Schippa, C.; Cozzolino, F.,
Volatile compounds in fresh pulp of pineapple (Ananas comosus [L.] Merr.) from French Polynesia,
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Lin, Fay, et al., 2000
Lin, J.; Fay, L.B.; Blank, I.,
Aroma impact compounds formed in meat-like model systems containing cysteine, ribose, and phospholipids
in Frontiers of Flavour Science, Scheberle, P.; Engel, K.-H., ed(s)., Deutsche Forschungsanstalt fur Lebensmittelchemie, Garching, 2000, 498-502. [all data]
Matsui, Guth, et al., 1998
Matsui, T.; Guth, H.; Grosch, W.,
A comparative study of potent odorants in peanut, hazelnut, and pumpkin seed oils on the basis of aroma extract dilution analysis (AEDA) and gas chromatography-olfactometry of headspace samples (GCOH),
Lipid - Fett, 1998, 100, 2, 51-56, https://doi.org/10.1002/(SICI)1521-4133(199802)100:2<51::AID-LIPI51>3.0.CO;2-W
. [all data]
Guth, 1997
Guth, H.,
Identification of character impact odorants of different white wine varieties,
J. Agric. Food Chem., 1997, 45, 8, 3022-3026, https://doi.org/10.1021/jf9608433
. [all data]
Lizárraga-Guerra, Guth, et al., 1997
Lizárraga-Guerra, R.; Guth, H.; López, M.G.,
Identification of the most potent odorants in huitlacoche (Ustilago maydis) and austern pilzen (Pleurotus sp.) by aroma extract dilution analysis and static head-space samples,
J. Agric. Food Chem., 1997, 45, 4, 1329-1332, https://doi.org/10.1021/jf960650f
. [all data]
Schermann and Schieberle, 1997
Schermann, P.; Schieberle, P.,
Evaluation of key odorants in milk chocolate and cocoa mass by aroma extract dilution analyses,
J. Agric. Food Chem., 1997, 45, 3, 867-872, https://doi.org/10.1021/jf960670h
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Schieberle, 1996
Schieberle, P.,
Odour-active compounds in moderately roasted sesame,
Food Chem., 1996, 55, 2, 145-152, https://doi.org/10.1016/0308-8146(95)00095-X
. [all data]
Guth and Grosch, 1994
Guth, H.; Grosch, W.,
Identification of the character impact odorants of stewed beef juice by instrumental analyses and sensory studies,
J. Agric. Food Chem., 1994, 42, 12, 2862-2866, https://doi.org/10.1021/jf00048a039
. [all data]
Guth and Grosch, 1993
Guth, H.; Grosch, W.,
12-Methyltridecanal, a species-specific odorant of stewed beef,
Lebensm. Wiss. Technol., 1993, 26, 2, 171-177, https://doi.org/10.1006/fstl.1993.1035
. [all data]
Blank, Sen, et al., 1992
Blank, I.; Sen, A.; Grosch, W.,
Potent odorants of the roasted powder and brew of Arabica coffee,
Z. Lebensm. Unters Forsch., 1992, 195, 3, 239-245, https://doi.org/10.1007/BF01202802
. [all data]
Notes
Go To: Top, Normal alkane RI, non-polar column, custom temperature program, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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