Coumarin

• Formula: C₉H₆O₂
• Molecular weight: 146.1427
• IUPAC Standard InChI: InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H Copy

  
• IUPAC Standard InChIKey: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 91-64-5
• 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.
• Isotopologues:
  • Coumarin-d6
• Other names: 2H-1-Benzopyran-2-one; cis-o-Coumarinic acid lactone; o-Hydroxycinnamic acid lactone; Benzo-α-pyrone; Coumarinic anhydride; Rattex; Tonka bean camphor; 1,2-Benzopyrone; 2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactone; 2H-Benzo[b]pyran-2-one; o-Hydroxycinnamic lactone; Cinnamic acid, o-hydroxy-, δ-lactone; Cumarin; 2-Oxo-1,2-benzopyran; 2H-1-Benzopyran, 2-oxo-; o-Hydroxyzimtsaure-lacton; Kumarin; NCI C07103; NSC 8774; 2H-Chromen-2-one
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
• Options:
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Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Gas phase thermochemistry data

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

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

Condensed phase thermochemistry data

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

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

Phase change data

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

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics data

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

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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

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

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

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

Watik and Sabbah, 1991
Watik, L.E.; Sabbah, R., Etude thermodynamique de la coumarine et de l'anthrone, Bull. Soc. Chim. Fr., 1991, 128, 344-349. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Serpinskii, Voitkevich, et al., 1958
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Yu., Trudy Vsesoyuz. Nauch.-Issledovatel. Inst. Sintet. I. Natural. Dushistykh Veshchestv, 1958, 4, 125. [all data]

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Matos, Sousa, et al., 2009
Matos, M. Agostinha R.; Sousa, Clara C.S.; Miranda, Margarida S.; Morais, Victor M.F.; Liebman, Joel F., Energetics of Coumarin and Chromone, J. Phys. Chem. B, 2009, 113, 32, 11216-11221, https://doi.org/10.1021/jp9026942 . [all data]

El Watik and Sabbah, 1991
El Watik, L.; Sabbah, R., Thermodynamic study of coumarin and anthrone, Bull. Soc. Chim. Fr., 1991, 344. [all data]

Sabbah and Watik, 1992
Sabbah, R.; Watik, L. El, Thermodynamic study of anthrone, coumarin and phenazine, Journal of Thermal Analysis, 1992, 38, 4, 803-809, https://doi.org/10.1007/BF01979412 . [all data]

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Sabbah and El Watik, 1992
Sabbah, R.; El Watik, L., Thermodynamic study of anthrone, counmarin and phenazine, J. Therm. Anal., 1992, 38, 803-809. [all data]

Serpinskii, Voitkevich, et al., 1953
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Y., Zh. Fiz. Khim., 1953, 27, 1032. [all data]

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El Watik and Sabbah, 1991, 2
El Watik, L.; Sabbah, R., Thermodynamic study of coumarin and anthrone, Bull. Soc. Chim. France, 1991, 128, 344-349. [all data]

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Soares, Monache, et al., 1999
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Tudor, 1997
Tudor, E., Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations, J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6 . [all data]

Velasco-Negueruela, Sanz, et al., 2004
Velasco-Negueruela, A.; Sanz, J.; Pérez-Alonso, M.J.; Palá-Paúl, J., The volatile components of the aerial parts of Melittis melissophyllum L. subsp. melissophyllum gathered in Spain, Botanica Complutensis, 2004, 28, 133-136. [all data]

Benkaci-Ali, Baaliouamer, et al., 2007
Benkaci-Ali, F.; Baaliouamer, A.; Meklati, B.Y.; Chemat, F., Chemical composition of seed essential oils from Algerian Nigella sativa extracted by microwave and hydrodistillation, Flavour Fragr. J., 2007, 22, 2, 148-153, https://doi.org/10.1002/ffj.1773 . [all data]

Mondello, Sciarrone, et al., 2007
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Zhou, Wintersteen, et al., 2002
Zhou, Q.; Wintersteen, C.L.; Cadwallader, K.R., Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey, J. Agric. Food Chem., 2002, 50, 7, 2016-2021, https://doi.org/10.1021/jf011436g . [all data]

Andriamaharavo, 2014
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Mondello, Casilli, et al., 2005
Mondello, L.; Casilli, A.; Tranchida, P.Q.; Dugo, G.; Dugo, P., Comprehensive two-dimensional gas chromatography in combination with rapid scanning quadrupole mass spectrometry in perfume analysis, J. Chromatogr. A, 2005, 1067, 1-2, 235-243, https://doi.org/10.1016/j.chroma.2004.09.040 . [all data]

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Chung, 2000
Chung, H.Y., Volatile flavor components in red fermented soybean (Glycine max) curds, J. Agric. Food Chem., 2000, 48, 5, 1803-1809, https://doi.org/10.1021/jf991272s . [all data]

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Shimoda, Shigematsu, et al., 1995, 2
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of volatile compounds among different grades of green tea and their relations to odor attributes, J. Agric. Food Chem., 1995, 43, 6, 1621-1625, https://doi.org/10.1021/jf00054a038 . [all data]

Bieri and Marriott, 2008
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Byun and Shin, 2008
Byun, Y.; Shin, S., Analysis of compounds and activity of essential oil from Chrysanthemum zawadskii var. latilobum and C. indicum agaunst antibiotic-resistant pathogenic bacteria, Nat. Prod. Sci., 2008, 14, 2, 138-142. [all data]

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Orlita, Sidwa-Gorycka, et al., 2008
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Mirza, M.; Navaei, M.N.; Dini, M., Volatile constituents of essential oils isolated from flowers and leaves of Eupatorium cannabinum L. from Iran, Iranian J. Pharmaceutical Res., 2006, 2, 149-152. [all data]

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Polzin, G.M.; Stanfill, S.B.; Brown, C.R.; Ashley, D.L.; Watson, C.H., Determination of eugenol, anethole, and coumarin in the mainstream cigarette smoke of Indonesian clove cigarettes, Food Chem. Toxicol., 2007, 45, 10, 1948-1953, https://doi.org/10.1016/j.fct.2007.04.012 . [all data]

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Kumazawa, K.; Sakai, N.; Amma, H.; Sakamoto, S.; Kodama, M.; Wada, Y.; Nishimura, O., Identification and formation of volatile components responsible for the characteristic aroma of Mat Rush (Igusa), Biosci. Biotechnol. Biochem., 2010, 74, 6, 1231-1236, https://doi.org/10.1271/bbb.100053 . [all data]

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Knobloch, T.; Engewald, W., Identification of some polar polycyclic compounds in emissions from brown-coal-fired residential stoves, J. Hi. Res. Chromatogr., 1993, 16, 4, 239-242, https://doi.org/10.1002/jhrc.1240160407 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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