Ambrafuran (AmbroxTM) Synthesis from Natural Plant Product Precursors.
Molecules
; 25(17)2020 Aug 25.
Article
em En
| MEDLINE
| ID: mdl-32854176
ABSTRACT
Ambergris, an excretion product of sperm whales, has been a valued agent in the formulation of perfumes. The composition of ambergris consists of two major components 40-46% cholestanol type steroids and approximately 25-45% of a triterpenoid known as ambrein. Ambergris undergoes oxidative decomposition in the environment to result in odorous compounds, such as ambraoxide, methylambraoxide, and ambracetal. Its oxidized form, ambrafuran (IUPAC name 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran), is a terpene furan with a pleasant odor and unique olfactive and fixative properties. The current state of the fragrance industry uses ambrafuran materials entirely from synthetic or semisynthetic sources. However, natural compounds with the potential to be converted to ambergris-like odorants have been extracted from several different types of plants. Here we review plant terpenoids suitable as starting materials for the semisyntheses of ambrafuran or intermediates, such as ambradiol, that can be used in biocatalytic transformations to yield ambrafuran.
Palavras-chave
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Produtos Biológicos
/
Colestanol
/
Furanos
/
Naftalenos
/
Naftóis
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article
País de afiliação:
África do Sul