Chemoenzymatic Synthesis of Fragrance Compounds from Stearic Acid.
Chembiochem
; 20(17): 2232-2235, 2019 09 02.
Article
en En
| MEDLINE
| ID: mdl-30983113
ABSTRACT
Fatty acids are versatile precursors for fuels, fine chemicals, polymers, perfumes, etc. The properties and applications of fatty acid derivatives depend on chain length and on functional groups and their positions. To tailor fatty acids for desired properties, an engineered P450 monooxygenase has been employed here for enhanced selective hydroxylation of fatty acids. After oxidation of the hydroxy groups to the corresponding ketones, Baeyer-Villiger oxidation could be applied to introduce an oxygen atom into the hydrocarbon chains to form esters, which were finally hydrolyzed to afford either hydroxylated fatty acids or dicarboxylic fatty acids. Using this strategy, we have demonstrated that the high-value-added flavors exaltolide and silvanone supra can be synthesized from stearic acid through a hydroxylation/carbonylation/esterification/hydrolysis/lactonization reaction sequence with isolated yields of about 36 % (for ω-1 hydroxylated stearic acid; 100, 60, 80, 75 % yields for the individual reactions, respectively) or 24 % (for ω-2 hydroxylated stearic acid). Ultimately, we obtained 7.91â
mg of exaltolide and 13.71â
mg of silvanone supra from 284.48â
mg stearic acid.
Palabras clave
Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Perfumes
/
Ácidos Esteáricos
/
Odorantes
Idioma:
En
Revista:
Chembiochem
Asunto de la revista:
BIOQUIMICA
Año:
2019
Tipo del documento:
Article
País de afiliación:
China