Ambroxan is a synthetic organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 belonging to the tetranorlabdane oxide class. It is generally present in a perfume

Perfume

Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...

 and shows aphrodisiac

Aphrodisiac

An aphrodisiac is a substance that increases sexual desire. The name comes from Aphrodite, the Greek goddess of sexuality and love. Throughout history, many foods, drinks, and behaviors have had a reputation for making sex more attainable and/or pleasurable...

 effects on animal. Ambergris is one derivative of ambroxan. Ambergris

Ambergris

Ambergris is a solid, waxy, flammable substance of a dull gray or blackish color produced in the digestive system of and regurgitated or secreted by sperm whales....

 is a metabolic product of the sperm whale

Sperm Whale

The sperm whale, Physeter macrocephalus, is a marine mammal species, order Cetacea, a toothed whale having the largest brain of any animal. The name comes from the milky-white waxy substance, spermaceti, found in the animal's head. The sperm whale is the only living member of genus Physeter...

 (Physeter macrocephalus) and is considered one of the most valuable animal perfumes besides civet, musk and castoroleum. Because of whale protection programs, the use of ambergris in perfumery has been abolished, thus encouraging chemists to search for new synthetic substitutes. (-)-Tetranorlabdane oxide is one of the commercially important products, first synthesized in 1950, and is commonly known under the trade names Ambrox (Firmenich), Amberlyn (Quest) and Ambroxan (Henkel).

Nowadays, an increasing number of publications on this topic demonstrates the great interest and importance of ambroxan derivatives. Many racemic

Racemic

In chemistry, a racemic mixture, or racemate , is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule. The first known racemic mixture was "racemic acid", which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid.- Nomenclature :A...

 and chiral syntheses have been described in the literature. Several naturally occurring terpenes are used in perfume for example, monoterpenes such as (+)-carvone and thujone, sesquiterpenes such as (-)-drimenol or diterpenes such as (-)-labdanolic acid, (+)-larixol, (+)-cis-abienol, (-)-levopimaric acid

Levopimaric acid

Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as antibacterial, cardiovascular and antioxidant. About...

, (-)-abietic acid, (-)-communic acid, (+)-manoyl oxide, and (-)-sclareol.
More recently, polyene

Polyene

Polyenes are poly-unsaturated organic compounds that contain one or more sequences of alternating double and single carbon-carbon bonds. These double carbon-carbon bonds interact in a process known as conjugation, which results in an overall lower energy state of the molecule.Organic compounds with...

s such as geranylacetone and homofarnesol, have been used for the synthesis of Ambroxan and enzymatic reactions have been employed for the resolution.