Амбреїн (ambreine)

Ambergris and ambrein

Ambergris is a solid, waxy, flammable substance of a dull grey or blackish colour produced in the digestive system of sperm whales. The main constituents of ambergris are ambrein, epi-coprosterol, coprosterol, cholesterol, and coprostane-3-one. Ambrein has a tricyclic triterpene structure with one tertiary hydroxyl group and two double bonds. Some squid beaks occasionally reach the hindgut of the sperm whale, and such beaks precipitate the formation of ambergris.

From ambrein to the odor of ambergris

The odor components of ambergris result from the photooxidative degradation of ambrein. Breakdown of the relatively scentless ambrein through oxidation produces ambroxide and ambrinol, the main odour components of ambergris. Ambroxide is an autoxidation product of ambrein. The oxidative degradation of ambrein is possibly a result of exposure to air, seawater and sunlight, catalyzed by the presence of copper.

Biosynthesis and production

Ambrein is synthesized from the common triterpenoid precursor squalene. The squalene-hopene cyclase (SHC) catalyzes the cyclization of squalene into the monocyclic 3-deoxyachilleol A, which tetraprenyl-beta-curcumene synthase (BmeTC) converts into the tricyclic ambrein. The biosynthetic pathway of ambrein in sperm whales remains unclear. Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage. Sclareol is the most common starting material for manufacturing ambroxide. Ambroxide is now produced synthetically and used extensively in the perfume industry.

Ambergris in nature

Ambergris can be found floating on the sea or washed up on coastlines. Ambergris is found primarily in the Atlantic Ocean and on the coasts of South Africa, Brazil and Madagascar, among other places. Most commercially collected ambergris comes from the Bahamas in the Atlantic, particularly New Providence.

Other properties

Ambrein has been shown to act as an analgesic. Ambrein has been proven to increase sexual behavior in rats. Ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits.

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Related: Aldambre · Ambrarome · Ambrein · Ambrettolide · Ambronova · Ammonia · Animal Notes · Beeswax