Kahweol

History

Kahweol was first isolated and identified as a constituent of coffee bean oil in 1932. The compound was isolated as its free "unsaponifiable" alcohol form. The solvent used greatly influences the crystal form, with acetone producing "large colorless trigonal or pentagonal dense plates," methanol producing "massive colorless quadratic plates," and ether producing "very long, snow-white silky needles."

While the presence of esters of cafestol (a hydrogenated analogue of kahweol) were apparent since the 1960s, it was not until 1982 that kahweol was isolated as an ester of its own. Following the development of liquid chromatography-mass spectrometry in the late 20th century, kahweol was isolated in other esteric forms, namely stearate, linoleate, and oleate, with minor amounts of arachidate and behenate.

Role in plants

Kahweol, and its related diterpenoid cafestol, are found in all parts of the coffee plant. Transferred from the endosperm to the seedling during germination, it may have a role in defense against insects and pathogenic fungi.

References

References

1. Surma, S.. (August 9, 2021). "Coffee and Arterial Hypertension". Current Hypertension Reports.
2. Bengis, R. O.. (1932-07-01). "The chemistry of the coffee-bean: I. Concerning the unsaponifiable matter of the coffee-bean oil. Preparation and properties of kahweol". Journal of Biological Chemistry.
3. (7 March 2022). "Human Metabolome Database: Showing metabocard for Kahweol (HMDB0035602)". Human Metabolome Database, Canada Foundation for Innovation.
4. Lam, Luke K. T.. (1982). "Isolation and Identification of Kahweol Palmitate and Cafestol Palmitate as Active Constituents of Green Coffee Beans That Enhance Glutathione S-Transferase Activity in the Mouse". Cancer Research.
5. Kurzrock, Torsten. (2001). "Identification of kahweol fatty acid esters in Arabica coffee by means of LC/MS". Journal of Separation Science.
6. Antoine, Gaëlle. (2023-01-01). "Diterpenes of Coffea seeds show antifungal and anti-insect activities and are transferred from the endosperm to the seedling after germination". Plant Physiology and Biochemistry.