Eugenol
- Formula: C10H12O2
- Molecular weight: 164.2011
- IUPAC Standard InChIKey: RRAFCDWBNXTKKO-UHFFFAOYSA-N
- CAS Registry Number: 97-53-0
- 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: Phenol, 2-methoxy-4-(2-propenyl)-; Phenol, 4-allyl-2-methoxy-; p-Allylguaiacol; p-Eugenol; Caryophyllic acid; Engenol; Eugenic acid; 2-Methoxy-1-hydroxy-4-allylbenzene; 2-Methoxy-4-allylphenol; 4-Allyl-2-methoxyphenol; 4-Allylguaiacol; 4-Hydroxy-3-methoxyallylbenzene; NCI-C50453; 1-Hydroxy-2-methoxy-4-allylbenzene; 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene; 2-Methoxy-4-(2-propenyl)phenol; 2-Methoxy-4-prop-2-enylphenol; 4-Allyl-1-hydroxy-2-methoxybenzene; 4-Allylcatechol-2-methyl ether; 1,3,4-Eugenol; FA 100; FEMA No. 2467; 2-Metoksy-4-allilofenol; 2-Hydroxy-5-allylanisole; Allylguaiacol; 4-(2-Propenyl)-2-methoxyphenol; NSC 209525; Phenol, 2-methoxy-4-(2-propen-1-yl)-; 4-allyl-2-methoxyphenol (eugenol); 4-(2-Propenyl)-2-methoxyphenol (eugenol); 4-Allyl-2-rnethoxyphenol (eugenol); Eugenol (2-Methoxy-4-(2-propenyl)phenol)
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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
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-5 | BPX-5 | BPX-5 | SLB-5MS | HP-5MS |
Column length (m) | 30. | 25. | 25. | 30. | 30. |
Carrier gas | He | He | He | He | |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.32 | 0.32 | 0.25 | 0.25 |
Phase thickness (μm) | 0.25 | 0.50 | 0.50 | 0.25 | 0.25 |
Program | 40C(2min) => 4C/min => 220C => 20C/min => 280C | 60 0C 6 0C/min -> 210 0C 10 0C/min -> 290 0C (20 min) | 60C => 6C/min => 210C => 10C/min => 290C (20min) | not specified | 50C(4min) => 10C/min => 200C(0.5min) => 20C/min => 260C(5min) |
I | 1356. | 1374. | 1371. | 1357. | 1346. |
Reference | Andrade, Sampaio, et al., 2007 | Eyres, Marriott, et al., 2007 | Eyres, Marriott, et al., 2007 | Mondello, Sciarrone, et al., 2007 | Pérez, Navarro, et al., 2007 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-5MS | BPX-5 | SE-52 | DB-5 | DB-5MS |
Column length (m) | 30. | 30. | 30. | 30. | 30. |
Carrier gas | He | He | He | ||
Substrate | |||||
Column diameter (mm) | 0.32 | 0.25 | 0.32 | 0.25 | 0.32 |
Phase thickness (μm) | 0.5 | 0.25 | 0.15 | 0.25 | 0.5 |
Program | 70C => 5C/min => 85C(1min) => 3C/min => 165C => 10C/min => 280C(3min) | 35C(5min) => 3C/min => 210C => 40C/min => 240C (4min) | 45C => 1C/min => 100C => 5C/min => 250C (10min) | 40C(2min) => 4C/min => 220C => 20C/min => 280C | 70C(1min) => 3C/min => 80C(1min) => 5C/min => 150C => 10C/min => 280C (4min) |
I | 1370. | 1390. | 1359. | 1357. | 1370. |
Reference | Varlet, Serot, et al., 2007 | Cardeal, da Silva, et al., 2006 | Guerrini, Sacchetti, et al., 2006 | Sampaio and Nogueira, 2006 | Varlet V., Knockaert C., et al., 2006 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | HP-5MS | 5 % Phenyl methyl siloxane | SPB-1 | DB-5 | SE-52 |
Column length (m) | 30. | 30. | 50. | 30. | 30. |
Carrier gas | He | He | He | He | |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.32 | 0.25 | 0.32 | 0.52 |
Phase thickness (μm) | 0.25 | 0.15 | 0.25 | 1. | 0.15 |
Program | 50C (3min) => 3C/min => 200C => 6C/min => 240C | 45C => 1C/min => 100C => 5C/min => 250C (10min) | 70C(3min) => 4C/min => 120C => 8C/min => 250C | 40C (2min) => 5C/min => 100C => 4C/min => 230C (10min) | 45C => 1C/min => 100C => 5C/min => 250C (10min) |
I | 1359. | 1359. | 1335. | 1366. | 1360. |
Reference | Akpulat, Tepe, et al., 2005 | Sacchetti, Maietti, et al., 2005 | Díaz-Maroto, Sánchez Palomo, et al., 2004 | Klesk, Qian, et al., 2004 | Sacchetti, Medici, et al., 2004 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-5 | DB-5 | CP Sil 8 CB | LM-5 | DB-5MS |
Column length (m) | 30. | 30. | 25. | 30. | 30. |
Carrier gas | He | He | He | He | H2 |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.32 | 0.32 | 0.25 | 0.25 |
Phase thickness (μm) | 0.25 | 1. | 0.25 | 0.25 | 0.25 |
Program | 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) | 60C(2min) => 15C/min => 180C => 5C/min => 280C(5min) | 40C (5min) => 2C/min => 200C => 5C/min => 250C (15min) |
I | 1370. | 1360. | 1369. | 1364.5 | 1341. |
Reference | Klesk and Qian, 2003 | Klesk and Qian, 2003, 2 | Fuhrmann and Grosch, 2002 | Ré-Poppi and Santiago-Silva, 2002 | Boulanger and Crouzet, 2001 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-5MS | SE-54 | SE-54 | SE-54 | HP-1 |
Column length (m) | 30. | 30. | 30. | 25. | 50. |
Carrier gas | H2/N2 | He | He | H2 | He |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.31 | 0.32 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 1.05 | |
Program | 40C (5min) => 2C/min => 200C => 5C/min => 250C (15min) | 35C(2min) => 40C/min => 60C => 6C/min => 180C 20C/min => 240C(10min) | 35C (2min) => 40C/min => 50C => 4C/min => 230C (10min) | not specified | 20C(0.5min) => 60C => 4C/min => 250C |
I | 1349. | 1356. | 1357. | 1366. | 1344. |
Reference | Boulanger and Crouzet, 2000 | Zimmermann and Schieberle, 2000 | Derail, Hofmann, et al., 1999 | Li, Wang, et al., 1998 | Sing, Smadja, et al., 1992 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
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.
Andrade, Sampaio, et al., 2007
Andrade, M.S.; Sampaio, T.S.; Nogueira, P.C.L.; Ribeiro, A.S.; Bittrich, V.; Amaral, M.C.E.,
Volatile compounds of the leaves, flowers and fruits of Kielmeyera rugosa Choisy (Clusiaceae),
Flavour Fragr. J., 2007, 22, 1, 49-52, https://doi.org/10.1002/ffj.1751
. [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]
Mondello, Sciarrone, et al., 2007
Mondello, L.; Sciarrone, D.; Casilli, A.; Tranchida, P.Q.; Dugo, P.; Dugo, G.,
Fast gas chromatography-full scan quadrupole mass spectrometry for the determination of allergens in fragrances,
J. Sep. Sci., 2007, 30, 12, 1905-1911, https://doi.org/10.1002/jssc.200600541
. [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]
Varlet, Serot, et al., 2007
Varlet, V.; Serot, T.; Cardinal, M.; Knockaert, C.; Prost, C.,
Olfactometric Determination of the Most Potent Odor-Active Compounds in Salmon Muscle (Salmo salar) Smoked by Using Four Smoke Generation Techniques,
J. Agric. Food Chem., 2007, 55, 11, 4518-4525, https://doi.org/10.1021/jf063468f
. [all data]
Cardeal, da Silva, et al., 2006
Cardeal, Z.L.; da Silva, M.D.R.G.; Marriott, P.J.,
Comprehensive two-dimensional gas chromatography/mass spectrometric analysis of pepper volatiles,
Rapid Commun. Mass Spectrom., 2006, 20, 19, 2823-2836, https://doi.org/10.1002/rcm.2665
. [all data]
Guerrini, Sacchetti, et al., 2006
Guerrini, A.; Sacchetti, G.; Muzzoli, M.; Rueda, G.M.; Medici, A.; Besco, E.; Bruni, R.,
Composition of the Volatile Fraction of Ocotea bofo Kunth (Lauraceae) Calyces by GC-MS and NMR Fingerprinting and Its Antimicrobial and Antioxidant Activity,
J. Agric. Food Chem., 2006, 54, 20, 7778-7788, https://doi.org/10.1021/jf0605493
. [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]
Varlet V., Knockaert C., et al., 2006
Varlet V.; Knockaert C.; Prost C.; Serot T.,
Comparison of odor-active volatile compounds of fresh and smoked salmon,
J. Agric. Food Chem., 2006, 54, 9, 3391-3401, https://doi.org/10.1021/jf053001p
. [all data]
Akpulat, Tepe, et al., 2005
Akpulat, H.A.; Tepe, B.; Sokmen, A.; Daferera, D.; Polissiou, M.,
Composition of the essential oils of Tanacetum argyrophyllum (C. Koch) Tvzel. var. argyrophyllum and Tanacetum parthenium (L.) Schultz Bip. (Asteraceae) from Turkey,
Biochem. Syst. Ecol., 2005, 33, 5, 511-516, https://doi.org/10.1016/j.bse.2004.10.006
. [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]
Díaz-Maroto, Sánchez Palomo, et al., 2004
Díaz-Maroto, M.C.; Sánchez Palomo, E.; Castro, L.; González Viñas, M.A.; Pérez-Coello, M.S.,
Changes produced in the aroma compounds and structural integrity of basil (Ocimum basilicum L) during drying,
J. Sci. Food Agric., 2004, 84, 15, 2070-2076, https://doi.org/10.1002/jsfa.1921
. [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]
Sacchetti, Medici, et al., 2004
Sacchetti, G.; Medici, A.; Maietti, S.; Radice, M.; Muzzoli, M.; Manfredini, S.; Braccioli, E.; Bruni, R.,
Composition and functional properties of the essential oil of Amazonian basil, Ocimum micranthum Willd., Labiatae in comparison with commercial essential oils,
J. Agric. Food Chem., 2004, 52, 11, 3486-3491, https://doi.org/10.1021/jf035145e
. [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]
Ré-Poppi and Santiago-Silva, 2002
Ré-Poppi, N.; Santiago-Silva, M.R.,
Identification of polycyclic aromatic hydrocarbons and methoxylated phenols in wood smoke emitted during production of charcoal,
Chromatographia, 2002, 55, 7/8, 475-481, https://doi.org/10.1007/BF02492280
. [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]
Boulanger and Crouzet, 2000
Boulanger, R.; Crouzet, J.,
Free and bound flavour components of Amazonian fruits: 3-glycosidically bound components of cupuacu,
Food Chem., 2000, 70, 4, 463-470, https://doi.org/10.1016/S0308-8146(00)00112-6
. [all data]
Zimmermann and Schieberle, 2000
Zimmermann, M.; Schieberle, P.,
Important odorants of sweet bell pepper powder (Capsicum annuum cv. annuum): differences between samples of Hungarian and Morrocan origin,
Eur. Food Res. Technol., 2000, 211, 3, 175-180, https://doi.org/10.1007/s002170050019
. [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]
Li, Wang, et al., 1998
Li, W.; Wang, H.; Sun, Y.; Huang, A.; Sun, Y.,
Capillary gas chromatographic analysis of volatile components in goat feces,
Fenxi Huaxue, 1998, 26, 8, 935-939. [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
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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