Concise synthesis of (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, components of the essential oil of marine green alga Ulva pertusa

Yoshihiko Akakabe; Kensuke Washizu; Kenji Matsui; Tadahiko Kajiwara

doi:10.1271/bbb.69.1348

Concise synthesis of (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, components of the essential oil of marine green alga Ulva pertusa

Biosci Biotechnol Biochem. 2005 Jul;69(7):1348-52. doi: 10.1271/bbb.69.1348.

Authors

Yoshihiko Akakabe¹, Kensuke Washizu, Kenji Matsui, Tadahiko Kajiwara

Affiliation

¹ Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8515, Japan. akakabe@yamaguchi-u.ac.jp

PMID: 16041141
DOI: 10.1271/bbb.69.1348

Abstract

The long-chain aldehydes, (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, were concisely synthesized by using Grignard coupling, catalytic hydrogenation with the Lindlar catalyst, and oxidation with Dess-Martin periodinane as the key steps. Particularly, (8Z,11Z,14Z)-8,11,14-heptadecatrienal and (7Z,10Z,13Z)-7,10,13-hexadecatrienal both possessed a seaweed-like odor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemical synthesis*
Aldehydes / chemistry
Models, Chemical
Odorants
Oils, Volatile / chemistry*
Ulva / chemistry*

Substances

Aldehydes
Oils, Volatile