TY - JOUR
T1 - Isolating valuable coffee diterpenes by using an inexpensive procedure
AU - Novaes, Fábio Junior Moreira
AU - Lima, Fernanda Alves
AU - Calado, Verônica
AU - Marriott, Philip John
AU - de Aquino Neto, Francisco Radler
AU - Rezende, Claudia Moraes
PY - 2020/9/15
Y1 - 2020/9/15
N2 - Cafestol and kahweol (C&K) are natural coffee diterpenes with high commercial value. There is thus interest in their synthesis although their isolation from natural products remains an alternative to recovering high quantities of C&K. The present work aimed at developing an isolation procedure to obtain C&K for both analytical purposes and in gram-scale from coffee beans. The procedure was divided into three steps: an initial saponification reaction optimized by Factorial Design, a choice of solvent for extraction of a crude C&K mixture based on Hansen Solubility Parameters, and a subsequent purification by column chromatography and preparative liquid chromatography in recycling mode to improve C&K mixture purity and for separate preparative collection of each diterpene. The first two steps are useful to maximize yield for C&K quantification, and the complete procedure allowed isolation of 1.5 g of C&K per 300 g of green coffee beans. This isolation procedure can be repeated 25 times using ca. US$1k in reagents, with an estimated value of product varying from US$227k to US$322k for a diterpene mass of 37.5 g, at the prevailing commercial rate.
AB - Cafestol and kahweol (C&K) are natural coffee diterpenes with high commercial value. There is thus interest in their synthesis although their isolation from natural products remains an alternative to recovering high quantities of C&K. The present work aimed at developing an isolation procedure to obtain C&K for both analytical purposes and in gram-scale from coffee beans. The procedure was divided into three steps: an initial saponification reaction optimized by Factorial Design, a choice of solvent for extraction of a crude C&K mixture based on Hansen Solubility Parameters, and a subsequent purification by column chromatography and preparative liquid chromatography in recycling mode to improve C&K mixture purity and for separate preparative collection of each diterpene. The first two steps are useful to maximize yield for C&K quantification, and the complete procedure allowed isolation of 1.5 g of C&K per 300 g of green coffee beans. This isolation procedure can be repeated 25 times using ca. US$1k in reagents, with an estimated value of product varying from US$227k to US$322k for a diterpene mass of 37.5 g, at the prevailing commercial rate.
KW - Coffea arabica
KW - Diterpenes cafestol and kahweol
KW - Experimental design
KW - Maximize preparative diterpene isolation
KW - Natural product scale-up
UR - http://www.scopus.com/inward/record.url?scp=85084751312&partnerID=8YFLogxK
U2 - 10.1016/j.indcrop.2020.112494
DO - 10.1016/j.indcrop.2020.112494
M3 - Article
AN - SCOPUS:85084751312
VL - 152
JO - Industrial Crops and Products
JF - Industrial Crops and Products
SN - 0926-6690
M1 - 112494
ER -