Lipase-assisted generation of 2-methyl-3-furanthiol and 2-furfurylthiol from thioacetates.
Enzymatic hydrolysis of S-3-(2-methylfuryl) thioacetate and S-2-furfuryl thioacetate using lipase from Candida rugosa produced 2-methyl-3-furanthiol and 2-furfurylthiol, respectively. When reactions were carried out at room temperature and pH 5.8, 2-methyl-3-furanthiol was produced in a optimal yield of 88% after 15 min of reaction, whereas 2-furfurylthiol was obtained in a yield of 80% after 1 h of reaction time. Enzymatic hydrolysis was also performed in n-hexane, n-pentane, and water/propylene glycol mixture. The reaction rates in these media were slower as compared to those in aqueous medium; however, the reaction yields were quite similar. As expected, the stability of the generated 2-methyl-3-furanthiol and 2-furfurylthiol was better in n-hexane, n-pentane, and the water/propylene glycol mixture as compared to that in water or phosphate buffer.
Bel Rhlid
Rachid
R
Nestlé Research Center, Nestec Ltd., Vers-chez-les-Blanc, P.O. Box 44, 1000 Lausanne 26, Switzerland. rachid.bel-rhlid@rdls.nestle.com
Matthey-Doret
Walter
W
Blank
Imre
I
Fay
Laurent B
LB
Juillerat
Marcel A
MA
D002175:Candida / Q000201:enzymology; D005421:Flavoring Agents; D005663:Furans / Q000378:metabolism*; D006586:Hexanes; D006868:Hydrolysis; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D009812:Odorants; D010420:Pentanes; D019946:Propylene Glycol; D013438:Sulfhydryl Compounds / Q000378:metabolism*; D014867:Water
D005421:Flavoring Agents; D005663:Furans; D006586:Hexanes; D010420:Pentanes; D013438:Sulfhydryl Compounds; D014867:Water; C455106:furfuryl mercaptan; C026385:n-hexane; C033353:pentane; D019946:Propylene Glycol; D008049:Lipase; C443400:2-methyl-3-furanthiol; C005732:thioacetic acid