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ChemicalBook CAS DataBase List Capsaicin
404-86-4

Capsaicin synthesis

10synthesis methods
From 3-chloro-2-isopropyltetrahydropyran; biosynthesis from Capsicum frutescens; separation from cis-capsaicin, pelargonic acid vanillamide and dihydrocapsaicin; reaction of capsaicin
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Yield:404-86-4 99.7 %

Reaction Conditions:

with Novozym 435 in di-isopropyl ether at 69;Dean-Stark;Solvent;Temperature;Reagent/catalyst;

Steps:

11; 15; 17; 22-25 Example 11: Preparation of capsaicin with excess amine in DIPE.

At normal atmospheric pressure (approximately 1 atm), 8-methyl-6-nonenoic acid (3.65 g), vanillyl amine (1.1 equiv.), Novozym 435(tm) on beads (498.8 mg, 14 w/w% E/S) were refluxed (about 69 oC) in diisopropyl ether (45 mL) with a Dean-Stark trap to collect the generated water. After stirring at about 300 rpm overnight (19 h), the mixture was filtered to recover the lipase catalyst, and the filtrate was washed with 0.5 M aqueous HCl solution (10 mL). The aqueous phase was extracted with Et2O (10 mL×2) and the organic phase were combined, dried over anhydrous Na2SO4 and concentrated to give 6.53 g product ( % yield, very pale yellow color).

References:

WO2022/229314,2022,A1 Location in patent:Page/Page column 25-26; 28-31

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