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] Small amounts (< 0.01 ppm) are used as a flavoring in food.[3] The FDA has approved the addition of ambroxide to food as a flavoring agent.[4]
The aroma is described as (characteristically) ambergris, sweet, labdanum, dry, woody, pine, cedar, green, and seedy.[5]
Ambroxide is highly tenacious and substantive. It clings to skin, fabric, and hard surfaces and persists for many hours, which is the basis of its role as a fixative. These properties make the molecule valuable both as a featured ingredient and as a behind-the-scenes performance booster.[6] The most prominent use of ambroxide is in fine fragrance, where it serves simultaneously as a base note and a fixative.
Synthesis
Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage.[7] Sclareol is oxidatively degraded to a lactone, which is hydrogenated to the corresponding diol.[8] The resulting compound is dehydrated to form ambroxide.[1]
Conversion of sclareol to ambroxide
While sclareol has been the historical method of synthesis of ambroxide, a new patented method was discovered that uses (3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-ol (Homofarnesol) [459-89-2] as the raw material. This process was stated to require 100 times less agricultural surface than the traditional method from clary sage.[9][10] The last step involves a polyene cyclization that is comparible to the process of squalene in the synthesis of steroids.[11]
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/.
- ↑ George A. Burdock (2010), Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, p. 1895
- ↑ "Substances Added to Food (formerly EAFUS)" (in en-US). https://hfpappexternal.fda.gov/scripts/fdcc/index.cfm?set=FoodSubstances&id=TETRAMETHYLOXATRICYCLOTRIDECANE.
- ↑ "ambroxan". Scents and Flavors. https://scentsandflavors.com/database/9dbb5068-e3d2-4ee0-9b55-1615d35ff7bc.
- ↑ "Bulk Buy - Ambroxide-Ambroxan-Ambrofix | Manufacturer-6790-58-5" (in en-GB). 2026-07-18. https://sinofoodsupply.com/ambroxide-ambroxan/.
- ↑ 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.
- ↑ "What’s Hot, What’s Not: The Trends of the Past 20 Years in the Chemistry of Odorants". Angewandte Chemie International Edition 59 (38): 16310–16344. 14 September 2020. doi:10.1002/anie.202005719. https://onlinelibrary.wiley.com/doi/10.1002/anie.202005719.
- ↑ "The catalytic asymmetric polyene cyclization of homofarnesol to ambrox". Nature 632 (8026): 795–801. 22 August 2024. doi:10.1038/s41586-024-07757-7. https://www.nature.com/articles/s41586-024-07757-7.
- ↑ https://cen.acs.org/synthesis/Chemists-make-popular-fragrance-compound/102/web/2024/08
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