ambrein

Description

Ambergris is an organic substance secreted from the digestive system of the sperm whale (Physeter macrocephalus), the only surviving species in its genus. It has a fecal odor when fresh, but as it ages it acquires a sweet aroma. It is often used as a fixative in perfumes to make the scent last longer.
The quest for ambergris (as well as for whalebone and whale oil) caused the sperm whale to become an endangered species in the 20th century. As a result, the Endangered Species Act of 1973 prohibited its possession and sale in the United States.
In 1946, chemists Leopold Ru?i?ka (a 1939 Nobel laureate) and F. Lardon at ETH Zurich reported that ambergris has three main components: the triterpene alcohol ambrein, the steroid alcohol epicoprostanol, and the steroid ketone coprostanone. Ambrein has only a mild scent, but it can be oxidized to produce the odor components ambroxide and ambrinol. Ambroxide (trade name Ambroxide) is widely used in the perfume industry; but because ambrein is now scarce, the industry relies on synthetic ambroxide.
But ambrein may have a second life. In 2019, Harald Pichler and colleagues at the Austrian Center of Industrial Biotechnology (Graz), Graz University of Technology, and ACS International (Plan‐les‐Ouates, Switzerland) engineered the yeast Saccharomyces cerevisiae to synthesize ambrein from squalene in good yields. In the long run, this may be a better way to produce ambroxide on a large scale.
Ambrein is not an article of commerce; hence hazard information for it is not readily available.

Chemical properties

Ambrein is the likely precursor of a number of strongly odoriferous mono-, bi-, and tricyclic compounds that are formed by autoxidation or photooxidation.

Chemical properties

Ambergris (ambra) is a secretion of the sperm whale Physeter catodon (P. macrocephalus L.), which possibly results from a pathological condition. Ambergris has a lower density than water and washes ashore along the ocean coasts.Themajor quantity is used to be obtained fromkilled animals, but only a low percentage contain ambergris in their intestines.
Fresh ambergris is almost black, but it turns light gray and develops a pleasant odorwhen exposed to light and seawater over a period of time.The major components of ambergris are epicoprosterol and the odorless triterpene alcohol, ambrein.

Definition

ChEBI: A triterpenoid alcohol that is a constituent of ambergris, an intestinal secretion of the sperm whale Physeter catodon.