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Ambroxide

(3aR,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan

Ambrox, Ambroxan, Ambrofix, Cetalox, (−)-Ambrox, Ambroxan, Ambrox

Tetracyclic ether (labdane-derived) · C₁₆H₂₈O

Chemical structure of Ambroxide
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
6790-58-5
Molecular formula
C₁₆H₂₈O
Molecular weight
236.40 g/mol
Introduced
1950 · Firmenich (Max Stoll and M. Hinder)
Origin
Nature-identical
Odor family
Amber
Note
Base
Aroma
Dry, clean amber with woody and mineral facets, like warm skin after sun; very diffusive and long lasting.

History

Ambroxide is the most important odorant of ambergris, formed when ambrein in ambergris slowly oxidises at sea. In 1950 Max Stoll and M. Hinder at Firmenich synthesised it from sclareol, a diterpene obtained from clary sage.

Several makers sell ambroxide under their own names: Ambrox (Firmenich), Ambroxan (Kao), Cetalox (Firmenich) and Ambrofix (Givaudan). Some newer processes use sugar fermentation to make the precursor instead of sclareol.

In perfumery

Ambroxide is a core material of the modern amber family. At low levels it adds diffusion and a warm skin effect; at high levels it can become the main note of a formula. The pairing of ambroxide with Iso E Super underlies many minimalist woody amber perfumes.

Connections

Evokesambergris
Found in natureAmbergris, Clary sage (via sclareol, a synthesis precursor)

Regulatory status

Unrestricted · No IFRA standard
IFRA 51
No dedicated IFRA Standard in the 51st Amendment index.
EU allergen 2023/1545
Not named individually in the expanded allergen list of Regulation 2023/1545.

Sources

  1. Wikidata Q2793438 (CAS 6790-58-5, formula; data mirrored from PubChem)
  2. Sell C.S. (ed.) The Chemistry of Fragrances: From Perfumer to Consumer, 2nd ed., Royal Society of Chemistry 2006
  3. Kraft P., Bajgrowicz J.A., Denis C., Fráter G. Odds and trends: recent developments in the chemistry of odorants. Angew. Chem. Int. Ed. 39 (2000) 2980–3010
  4. IFRA Standards, 51st Amendment: Index of IFRA Standards (notified 30 June 2023)
  5. dsm-firmenich, Ambrox product page