Chemistry:Ambroxide
Ambroxide, widely known by the brand name Ambroxan, is a naturally occurring terpenoid and one of the key constituents responsible for the odor of ambergris. It is an autoxidation product of ambrein.[1] Ambroxide is used in perfumery for creating ambergris notes and as a fixative.[1] Ambroxide has a scent with woody, musky and slightly salty nuances.[2] Another name for ambroxan is ambrocenide.[3] Small amounts (< 0.01 ppm) are used as a flavoring in food.[4]
The aroma is described as (characteristically) ambergris, sweet, labdanum, dry, woody, pine, cedar, green, and seedy.[5]
Synthesis
Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage.[6] Sclareol is oxidatively degraded to a lactone, which is hydrogenated to the corresponding diol.[7] The resulting compound is dehydrated to form ambroxide.[1]
Conversion of sclareol to ambroxide
References
- ↑ 1.0 1.1 1.2 Karl-Georg Fahlbusch (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 72
- ↑ "Разница серой амбры и ноты амбры. Синтетические аналоги амбры.". https://syntheticamber.ru/.
- ↑ "Амброценид: химия и аромат в мире парфюмерии". https://ambrocenide.ru/.
- ↑ George A. Burdock (2010), Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, p. 1895
- ↑ "ambroxan". Scents and Flavors. https://scentsandflavors.com/database/9dbb5068-e3d2-4ee0-9b55-1615d35ff7bc.
- ↑ Brian M Lawrence (2003). Essential Oils 1995-2000. Allured Pub.. ISBN 0-931710-94-4.
- ↑ Dub, Pavel A.; Gordon, John C. (2018). "The role of the metal-bound N–H functionality in Noyori-type molecular catalysts". Nature Reviews Chemistry 2 (12): 396–408. doi:10.1038/s41570-018-0049-z.
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