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 ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
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Gas phase ion energetics data

Go To: Top, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References, Notes

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

UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

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 ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

Redchenko, Safronov, et al., 1992
Redchenko, V.V.; Safronov, A.I.; Kirpichenok, M.A.; Grandberg, I.I.; Traven', V.F., Electronic structure of π-systems. XV. Photoelectron spectra of 7-aminocoumarin derivatives, J. Gen. Chem. USSR, 1992, 62, 2313. [all data]

Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L., Energetic considerations in the assignment of some fragment ion structures, Australian J. Chem., 1968, 21, 997. [all data]

Tang, McGowan, et al., 1979
Tang, S.-Y.; McGowan, J.C.; Singh, M.; Galatsis, P.; Ellis, B.E.; Boyd, R.K.; Brown, S.A., Mass spectrometry of some furanocoumarins, Can. J. Chem., 1979, 57, 1995. [all data]

Barnes and Occolowitz, 1964
Barnes, C.S.; Occolowitz, J.L., The mass spectra of some naturally occurring oxygen heterocycles and related compounds, Australian J. Chem., 1964, 17, 975. [all data]

Ikawa and Link., 1950
Ikawa, M.; Link., K.P., J. Am. Chem. Soc., 1950, 72, 4373. [all data]

Soares, Monache, et al., 1999
Soares, M.F.; Monache, F.D.; Heinzen, V.E.F.; Yunes, R.A., Prediction of gas chromatographic retention indices of coumarins, J. Braz. Chem. Soc., 1999, 10, 3, 189-196, https://doi.org/10.1590/S0103-50531999000300006 . [all data]

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
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]

Dallüge, van Stee, et al., 2002
Dallüge, J.; van Stee, L.L.P.; Xu, X.; Williams, J.; Beens, J.; Vreuls, R.J.J.; Brinkman, U.A.Th., Unravelling the composition of very complex samples by comprehensive gas chromatography coupled to time-of-flight mass spectrometry. Cigarette smoke, J. Chromatogr. A, 2002, 974, 1-2, 169-184, https://doi.org/10.1016/S0021-9673(02)01384-5 . [all data]

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]

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]

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]

Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion, J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037 . [all data]

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
Bieri, S.; Marriott, P.J., Dual-injection system with multiply injections for determining sidimentional retention indexes in comprehensive two-dimensional gas chromatography, Anal. Chem., 2008, 80, 3, 760-768, https://doi.org/10.1021/ac071367q . [all data]

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]

Mondello, Casilli, et al., 2008
Mondello, L.; Casilli, A.; Tranchida, Q.; Sciarrone, D.; Dugo, P.; Dugo, G., Analysis of allergens in fragrances using multiple heart-cut multidimentional gas chromatography - mass spectrometry, LC-GC Europe, 2008, 21, 130. [all data]

Orlita, Sidwa-Gorycka, et al., 2008
Orlita, A.; Sidwa-Gorycka, M.; Kumirska, J.; Malinski, E.; Siedlecka, E.M.; Gajdus, J.; Lojkowska, E.; Stepnowski, P., Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors, Biotechnol. Prog., 2008, 24, 1, 128-133, https://doi.org/10.1021/bp070261d . [all data]

Zeller and Rychlik, 2007
Zeller, A.; Rychlik, M., Impact of estragole and other odorants on the flavour of anise and tarragon, Flavour Fragr. J., 2007, 22, 2, 105-113, https://doi.org/10.1002/ffj.1765 . [all data]

Mirza, Navaei, et al., 2006
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]

Schlumpberger B.O., Clery R.A., et al., 2006
Schlumpberger B.O.; Clery R.A.; Barthlott W., A unique cactus with scented and possibly bat-dispersed fruits: Rhipsalis juengeri, Plant Biology, 2006, 8, 2, 265-270, https://doi.org/10.1055/s-2005-873045 . [all data]

Tellez, Khan, et al., 2004
Tellez, M.R.; Khan, I.A.; Schaneberg, B.T.; Crockett, S.L.; Rimando, A.M.; Kobaisy, M., Steam distillation-solid-phase microextraction for the detection of Ephedra sinica in herbal preparations, J. Chromatogr. A, 2004, 1025, 1, 51-56, https://doi.org/10.1016/S0021-9673(03)01035-5 . [all data]

Tellez, Canel, et al., 1999
Tellez, M.R.; Canel, C.; Rimando, A.M.; Duke, S.O., Differential accumulation of isoprenoids in glanded and glandless Artemisia annua L, Phytochemistry, 1999, 52, 6, 1035-1040, https://doi.org/10.1016/S0031-9422(99)00308-8 . [all data]

Egolf and Jurs, 1993
Egolf, L.M.; Jurs, P.C., Quantitative structure-retention and structure-odor intensity relationships for a diverse group of odor-active compounds, Anal. Chem., 1993, 65, 21, 3119-3126, https://doi.org/10.1021/ac00069a027 . [all data]

Maggi, Bilek, et al., 2009
Maggi, F.; Bilek, T.; Lucarini, D.; Papa, F.; Sagratini, G.; Vittori, S., Melittis melissophyllum L. subsp. melissophylum (Lamiaceae) from central Italy: A new source of a mushrrom-like flavour, Food Chem., 2009, 113, 1, 216-221, https://doi.org/10.1016/j.foodchem.2008.07.066 . [all data]

Zhu, Li, et al., 2008
Zhu, M.; Li, E.; He, H., Determination of volatile chemical constitutes in tea by simultaneous distillation extraction, vacuum hydrodistillation and thermal desrption, Chromatographia, 2008, 68, 7/8, 603-610, https://doi.org/10.1365/s10337-008-0732-1 . [all data]

Polzin, Stanfill, et al., 2007
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]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Guyot-Declerck, Renson, et al., 2002
Guyot-Declerck, C.; Renson, S.; Bouseta, A.; Collin, S., Floral quality and discrimination of Lavandula stoechas, Lavandula angustifolia, and Lavandula angustifolia × latifolia honeys, Food Chem., 2002, 79, 4, 453-459, https://doi.org/10.1016/S0308-8146(02)00216-9 . [all data]

Guyot, Bouseta, et al., 1998
Guyot, C.; Bouseta, A.; Scheirman, V.; Collin, S., Floral origin markers of chestnut and lime tree honeys, J. Agric. Food Chem., 1998, 46, 2, 625-633, https://doi.org/10.1021/jf970510l . [all data]

Grundschober, 1991
Grundschober, F., The identification of individual components in flavourings and flavoured foods, Z. Lebensm. Unters. Forsch., 1991, 192, 6, 530-534, https://doi.org/10.1007/BF01202508 . [all data]

Shibamoto, 1987
Shibamoto, T., Retention Indices in Essential Oil Analysis in Capillary Gas Chromatography in Essential Oil Analysis, Sandra, P.; Bicchi, C., ed(s)., Hutchig Verlag, Heidelberg, New York, 1987, 259-274. [all data]

Kumazawa, Sakai, et al., 2010
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]

Soria, Sanz, et al., 2008
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Kumazawa and Masuda, 2002
Kumazawa, K.; Masuda, H., Identification of potent odorants in different green tea varieties using flavor dilution technique, J. Agric. Food Chem., 2002, 50, 20, 5660-5663, https://doi.org/10.1021/jf020498j . [all data]

Kumazawa and Masuda, 1999
Kumazawa, K.; Masuda, H., Identification of potent odorants in Japanese green tea (Sen-cha), J. Agric. Food Chem., 1999, 47, 12, 5169-5172, https://doi.org/10.1021/jf9906782 . [all data]

Buttery, Parker, et al., 1981
Buttery, R.G.; Parker, F.D.; Teranishi, R.; Mon, T.R.; Ling, L.C., Volatile components of alfalfa leaf-cutter bee cells, J. Agric. Food Chem., 1981, 29, 5, 955-958, https://doi.org/10.1021/jf00107a017 . [all data]

Knobloch and Engewald, 1993
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 ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy

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