Crotonic acid

Formula: C₄H₆O₂
Molecular weight: 86.0892
IUPAC Standard InChI: InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)
IUPAC Standard InChIKey: LDHQCZJRKDOVOX-UHFFFAOYSA-N
CAS Registry Number: 3724-65-0
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Stereoisomers:
Other names: 2-Butenoic acid; α-Butenoic acid; 3-Methylacrylic acid; CH3CH=CHCOOH; α-Crotonic acid; β-Methylacrylic acid; Acrylic acid, 3-methyl-; Kyselina krotonova; UN 2823; But-2-enoic acid; NSC 206946; 2-Butenoic acid, isomer # 2
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-368.5 ± 1.4	kJ/mol	Ccb	Van-chin-syan, Kochubei, et al., 1996

Gas Chromatography

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

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-101	986.	Politeo, Jukic, et al., 2007	25. m/0.20 mm/0.20 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 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-20M	1708.	Politeo, Jukic, et al., 2007	50. m/0.20 mm/0.20 μm, Helium, 70. C @ 4. min, 4. K/min, 180. C @ 15. min
Capillary	HP-20M	1709.	Politeo, Jukic, et al., 2007, 2	50. m/0.2 mm/0.2 μm, He, 70. C @ 4. min, 4. K/min, 180. C @ 15. min
Capillary	DB-Wax	1773.	Shiratsuchi, Shimoda, et al., 1993	60. m/0.25 mm/0.25 μm, 50. C @ 4. min, 2. K/min, 230. C @ 30. min
Capillary	DB-Wax	1773.	Shiratsuchi, Shimoda, et al., 1993	60. m/0.25 mm/0.25 μm, 50. C @ 4. min, 2. K/min, 230. C @ 30. min

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1744.	Parada, Duque, et al., 2000	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min
Capillary	DB-Wax	1763.	Parada, Duque, et al., 2000	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min
Capillary	DB-Wax	1744.	Parada and Duque, 1998	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min
Capillary	DB-Wax	1746.	Parada and Duque, 1998	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min

References

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Van-chin-syan, Kochubei, et al., 1996
Van-chin-syan, Yu.Ya.; Kochubei, V.V.; Sergeev, V.V.; Raevskii, Yu.A.; Gerasimchuk, S.I.; Kotovich, Kh.Z., Thermodynamic properties of some acids and aldehydes of the acrylic series, Sov. J. Chem. Phys. (Engl. Transl.), 1996, 70, 1789-1794, In original 1932. [all data]

Politeo, Jukic, et al., 2007
Politeo, O.; Jukic, M.; Milos, M., Chemical Composition and Antioxidant Activity of Free Volatile Aglycones from Laurel (Laurus nobilis L.) Compared to Its Essential Oil, Croatica Chem. Acta, 2007, 80, 1, 121-126. [all data]

Politeo, Jukic, et al., 2007, 2
Politeo, O.; Jukic, M.; Milos, M., Chemical composition and antioxidant capacity of free volatile aglycones from basil (Ocimum basilicum L.) compared with its essential oil, Food Chem., 2007, 101, 1, 379-385, https://doi.org/10.1016/j.foodchem.2006.01.045 . [all data]

Shiratsuchi, Shimoda, et al., 1993
Shiratsuchi, H.; Shimoda, M.; Minegishi, Y.; Osajima, Y., Isolation and identification of volatile flavor compounds in nonfermented coarse-cut sausage. Flavor as a quality factor of nonfermented sausage. 1, J. Agric. Food Chem., 1993, 41, 4, 647-652, https://doi.org/10.1021/jf00028a027 . [all data]

Parada, Duque, et al., 2000
Parada, F.; Duque, C.; Fujimoto, Y., Free and bound volatile composition and characterization of some glucoconjugates as aroma precursors in Melón de olor fruit pulp (Sicana odorifera), J. Agric. Food Chem., 2000, 48, 12, 6200-6204, https://doi.org/10.1021/jf0007232 . [all data]

Parada and Duque, 1998
Parada, F.; Duque, C., Studies on the aroma of piñuela fruit pulp (Bromelia plumieri): Free and bound volatile composition and characterization of some glucoconjugates as aroma precursors, J. Hi. Res. Chromatogr., 1998, 21, 10, 577-581, https://doi.org/10.1002/(SICI)1521-4168(19981001)21:10<577::AID-JHRC577>3.0.CO;2-V . [all data]

Notes

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Symbols used in this document:

Δ_fH°_gas Enthalpy of formation of gas at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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