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Formation of volatile chemicals from thermal degradation of less volatile coffee components: quinic acid, caffeic acid, and chlorogenic acid.
J Agric Food Chem. 2010 May 12; 58(9):5465-70.JA

Abstract

The less volatile constituents of coffee beans (quinic acid, caffeic acid, and chlorogenic acid) were roasted under a stream of nitrogen, air, or helium. The volatile degradation compounds formed were analyzed by gas chromatography and gas chromatography-mass spectrometry. Caffeic acid produced the greatest amount of total volatiles. Quinic acid and chlorogenic acid produced a greater number of volatiles under the nitrogen stream than under the air stream. These results suggest that the presence of oxygen does not play an important role in the formation of volatile compounds by the heat degradation of these chemicals. 2,5-Dimethylfuran formed in relatively large amounts (59.8-2231.0 microg/g) in the samples obtained from quinic acid and chlorogenic acid but was not found in the samples from caffeic acid. Furfuryl alcohol was found in the quinic acid (259.9 microg/g) and caffeic acid (174.4 microg/g) samples roasted under a nitrogen stream but not in the chlorogenic sample. The three acids used in the present study do not contain a nitrogen atom, yet nitrogen-containing heterocyclic compounds, pyridine, pyrrole, and pyrazines, were recovered. Phenol and its derivatives were identified in the largest quantities. The amounts of total phenols ranged from 60.6 microg/g (quinic acid under helium) to 89893.7 microg/g (caffeic acid under helium). It was proposed that phenol was formed mainly from quinic acid and that catechols were formed from caffeic acid. Formation of catechol from caffeic acid under anaerobic condition indicates that the reaction participating in catechol formation was not oxidative degradation.

Authors+Show Affiliations

Department of Environmental Toxicology, University of California, Davis, Davis, California 95616, USA.No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20405916

Citation

Moon, Joon-Kwan, and Takayuki Shibamoto. "Formation of Volatile Chemicals From Thermal Degradation of Less Volatile Coffee Components: Quinic Acid, Caffeic Acid, and Chlorogenic Acid." Journal of Agricultural and Food Chemistry, vol. 58, no. 9, 2010, pp. 5465-70.
Moon JK, Shibamoto T. Formation of volatile chemicals from thermal degradation of less volatile coffee components: quinic acid, caffeic acid, and chlorogenic acid. J Agric Food Chem. 2010;58(9):5465-70.
Moon, J. K., & Shibamoto, T. (2010). Formation of volatile chemicals from thermal degradation of less volatile coffee components: quinic acid, caffeic acid, and chlorogenic acid. Journal of Agricultural and Food Chemistry, 58(9), 5465-70. https://doi.org/10.1021/jf1005148
Moon JK, Shibamoto T. Formation of Volatile Chemicals From Thermal Degradation of Less Volatile Coffee Components: Quinic Acid, Caffeic Acid, and Chlorogenic Acid. J Agric Food Chem. 2010 May 12;58(9):5465-70. PubMed PMID: 20405916.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Formation of volatile chemicals from thermal degradation of less volatile coffee components: quinic acid, caffeic acid, and chlorogenic acid. AU - Moon,Joon-Kwan, AU - Shibamoto,Takayuki, PY - 2010/4/22/entrez PY - 2010/4/22/pubmed PY - 2010/8/7/medline SP - 5465 EP - 70 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 58 IS - 9 N2 - The less volatile constituents of coffee beans (quinic acid, caffeic acid, and chlorogenic acid) were roasted under a stream of nitrogen, air, or helium. The volatile degradation compounds formed were analyzed by gas chromatography and gas chromatography-mass spectrometry. Caffeic acid produced the greatest amount of total volatiles. Quinic acid and chlorogenic acid produced a greater number of volatiles under the nitrogen stream than under the air stream. These results suggest that the presence of oxygen does not play an important role in the formation of volatile compounds by the heat degradation of these chemicals. 2,5-Dimethylfuran formed in relatively large amounts (59.8-2231.0 microg/g) in the samples obtained from quinic acid and chlorogenic acid but was not found in the samples from caffeic acid. Furfuryl alcohol was found in the quinic acid (259.9 microg/g) and caffeic acid (174.4 microg/g) samples roasted under a nitrogen stream but not in the chlorogenic sample. The three acids used in the present study do not contain a nitrogen atom, yet nitrogen-containing heterocyclic compounds, pyridine, pyrrole, and pyrazines, were recovered. Phenol and its derivatives were identified in the largest quantities. The amounts of total phenols ranged from 60.6 microg/g (quinic acid under helium) to 89893.7 microg/g (caffeic acid under helium). It was proposed that phenol was formed mainly from quinic acid and that catechols were formed from caffeic acid. Formation of catechol from caffeic acid under anaerobic condition indicates that the reaction participating in catechol formation was not oxidative degradation. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/20405916/Formation_of_volatile_chemicals_from_thermal_degradation_of_less_volatile_coffee_components:_quinic_acid_caffeic_acid_and_chlorogenic_acid_ L2 - https://doi.org/10.1021/jf1005148 DB - PRIME DP - Unbound Medicine ER -