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Aroma Profile of Galangal Composed of Cinnamic Acid Derivatives and Their Structure-Odor Relationships.
Nat Prod Commun. 2016 Oct; 11(10):1463-1469.NP

Abstract

Cinnamic acid derivatives are important odorants due to their characteristic scent. Some fragrance materials, such as cinnamon bark, matsutake mushrooms, and Kaempferia galanga L. rhizome (galangal), contain several cinnamic acid derivatives as important odor constituents. The main odor constituent of glangal is (E)-ethyl 4-methoxycinnamate, but the odor of this compound is different from that of galangal. We investigated the aroma profile of galangal using our previously described method that considers the intermolecular interactions of the odorant compounds with their receptors. Odorant compounds in galangal were extracted by hexane extraction, steam distillation, and headspace sampling. The odor of the hexane extract was different from that of the steam - distillate and similar to that of galangal; therefore, we searched for the key compounds contributing to the aroma profile of galangal by separating the constituents of the hexane extract. A fraction with a galangal-like odor was obtained by bulb-to-bulb distillation of the hexane extract. The main component of this fraction was not (E)-ethyl 4-methoxycinnamate, but rather ethyl cinnamate. These results indicate that ethyl cinnamate is more important in the aroma profile of galangal than (E)-ethyl 4-methoxycinnamate. GC-MS analysis revealed that this fraction contained aromatic compounds, cyclic terpenes, and linear chain compounds in addition to ethyl cinnamate. We synthesized cinnamic acid derivatives and examined the importance of the odor expression of these cinnamic acid derivatives. Cinnamic acid derivatives lacking a p-methoxy group had a strong fruity odor. Replacement of the hydrogen atom at the para position with a methoxy group altered and weakened the odor. We found that a p-methoxy group in cinnamic acid derivatives plays an important role in the aroma profile of galangal.

Authors

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Pub Type(s)

Journal Article

Language

eng

PubMed ID

30549600

Citation

Hasegawa, Toshio, et al. "Aroma Profile of Galangal Composed of Cinnamic Acid Derivatives and Their Structure-Odor Relationships." Natural Product Communications, vol. 11, no. 10, 2016, pp. 1463-1469.
Hasegawa T, Hashimoto M, Fujihara T, et al. Aroma Profile of Galangal Composed of Cinnamic Acid Derivatives and Their Structure-Odor Relationships. Nat Prod Commun. 2016;11(10):1463-1469.
Hasegawa, T., Hashimoto, M., Fujihara, T., & Yamada, H. (2016). Aroma Profile of Galangal Composed of Cinnamic Acid Derivatives and Their Structure-Odor Relationships. Natural Product Communications, 11(10), 1463-1469.
Hasegawa T, et al. Aroma Profile of Galangal Composed of Cinnamic Acid Derivatives and Their Structure-Odor Relationships. Nat Prod Commun. 2016;11(10):1463-1469. PubMed PMID: 30549600.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Aroma Profile of Galangal Composed of Cinnamic Acid Derivatives and Their Structure-Odor Relationships. AU - Hasegawa,Toshio, AU - Hashimoto,Momohiro, AU - Fujihara,Takashi, AU - Yamada,Hideo, PY - 2018/12/15/entrez PY - 2016/10/1/pubmed PY - 2016/10/1/medline SP - 1463 EP - 1469 JF - Natural product communications JO - Nat Prod Commun VL - 11 IS - 10 N2 - Cinnamic acid derivatives are important odorants due to their characteristic scent. Some fragrance materials, such as cinnamon bark, matsutake mushrooms, and Kaempferia galanga L. rhizome (galangal), contain several cinnamic acid derivatives as important odor constituents. The main odor constituent of glangal is (E)-ethyl 4-methoxycinnamate, but the odor of this compound is different from that of galangal. We investigated the aroma profile of galangal using our previously described method that considers the intermolecular interactions of the odorant compounds with their receptors. Odorant compounds in galangal were extracted by hexane extraction, steam distillation, and headspace sampling. The odor of the hexane extract was different from that of the steam - distillate and similar to that of galangal; therefore, we searched for the key compounds contributing to the aroma profile of galangal by separating the constituents of the hexane extract. A fraction with a galangal-like odor was obtained by bulb-to-bulb distillation of the hexane extract. The main component of this fraction was not (E)-ethyl 4-methoxycinnamate, but rather ethyl cinnamate. These results indicate that ethyl cinnamate is more important in the aroma profile of galangal than (E)-ethyl 4-methoxycinnamate. GC-MS analysis revealed that this fraction contained aromatic compounds, cyclic terpenes, and linear chain compounds in addition to ethyl cinnamate. We synthesized cinnamic acid derivatives and examined the importance of the odor expression of these cinnamic acid derivatives. Cinnamic acid derivatives lacking a p-methoxy group had a strong fruity odor. Replacement of the hydrogen atom at the para position with a methoxy group altered and weakened the odor. We found that a p-methoxy group in cinnamic acid derivatives plays an important role in the aroma profile of galangal. SN - 1934-578X UR - https://www.unboundmedicine.com/medline/citation/30549600/Aroma_Profile_of_Galangal_Composed_of_Cinnamic_Acid_Derivatives_and_Their_Structure_Odor_Relationships_ DB - PRIME DP - Unbound Medicine ER -