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 compound, organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeabl ...

and one of the key constituents responsible for the odor of

ambergris Ambergris ( or ; ; ), ''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 marine, fecal odor. It acquires a sw ...

. 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 (, ) is a mixture of fragrance, fragrant essential oils or aroma compounds (fragrances), Fixative (perfumery), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agre ...

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 that is used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of ...

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 alcohol. It is an amber colored solid with a sweet, balsamic scent. In an experiment in which scla ...

, a component of the

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...

of clary sage. Sclareol is oxidatively degraded to a

lactone Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated. Lactones are formed by lactonization, the intramolecular esterification of the corresp ...

, which is hydrogenated to the corresponding

diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...

. The resulting compound is

dehydrated In physiology, dehydration is a lack of total body water that disrupts Metabolism, metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of wate ...

to form ambroxide. : Ambroxide synthesis sclareol

References

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