Ambroxide, widely known by the brand name Ambroxan, is a naturally occurring

terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes" ...

and one of the key constituents responsible for the odor of

ambergris Ambergris ( or , la, ambra grisea, fro, ambre gris), ''ambergrease'', or grey amber is a solid, waxy, flammable substance of a dull grey or blackish colour produced in the digestive system of sperm whales. Freshly produced ambergris has a mari ...

. It is an

autoxidation Autoxidation (sometimes auto-oxidation) refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organi ...

product of ambrein. Ambroxide is used in

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

ry for creating

notes and as a fixative. Small amounts (< 0.01 ppm) are used as a

flavoring A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gusta ...

in food.

Synthesis

Ambroxide is synthesized from

sclareol Sclareol is a fragrant chemical compound found in '' Salvia sclarea'', from which it derives its name. It is classified as a bicyclic diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecul ...

, a component of the essential oil of

clary sage ''Salvia sclarea'', the clary or clary sage, is a biennial or short-lived herbaceous perennial in the genus ''Salvia''. It is native to the northern Mediterranean Basin, along with some areas in north Africa and Central Asia. The plant has a leng ...

. Sclareol is oxidatively degraded to a

lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ...

, which is

hydrogenated Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic co ...

to the corresponding

diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. The most common industrial diol is e ...

. The resulting compound is

dehydrated In physiology, dehydration is a lack of total body water, with an accompanying disruption of metabolic processes. It occurs when free water loss exceeds free water intake, usually due to exercise, disease, or high environmental temperature. Mil ...

to form ambroxide. : Ambroxide synthesis sclareol

References

{{reflist Perfume ingredients Flavors Terpenes and terpenoids Tetrahydrofurans Decalins Heterocyclic compounds with 3 rings