ChemicalBook CAS DataBase List Capsaicin

Capsaicin synthesis

10synthesis methods

Product Name:Capsaicin
CAS Number:404-86-4
Molecular formula:C18H27NO3
Molecular Weight:305.41

From 3-chloro-2-isopropyltetrahydropyran; biosynthesis from Capsicum frutescens; separation from cis-capsaicin, pelargonic acid vanillamide and dihydrocapsaicin; reaction of capsaicin

1196-92-5
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59320-77-3
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404-86-4
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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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7149-10-2 Synthesis