Article · Wikipedia archive · Last revised Jun 5, 2026

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. Ambroxide is used in perfumery for creating ambergris notes and as a fixative. Ambroxide has a scent with woody, musky and slightly salty nuances. Small amounts are used as a flavoring in food.

Last revised
Jun 5, 2026
Read time
≈ 2 min
Length
371 w
Citations
9
Source
Wikipedia ↗
Ambroxide
source ↗
Names
Preferred IUPAC name
(3aR,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan
Other names
Ambrox (Firmenich)
Ambrofix (Givaudan)
Ambroxan (Kao)1
Ambermox
Ambermor
Orcanox
(3aR-(3aα,5aβ,9aα,9bβ))-Dodecahydro-3a,6,6,9a-tetra-methylnaphtho(2,1-b)furan;
Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-,;
8α, 12-Oxido-13,14,15,16-tetranorlabdane;
1,5,5,9-Tetramethyl-13-oxatricyclo(8.3.0.0(4,9))tridecane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.027.147
EC Number
  • 229-861-2
UNII
  • InChI=1S/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3/t12-,13+,15-,16+/m0/s1 checkY
    Key: YPZUZOLGGMJZJO-LQKXBSAEBI ☒N
  • InChI=1S/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3/t12-,13+,15-,16+/m0/s1
  • CC1(CCC[C@]2([C@H]1CC[C@@]3([C@@H]2CCO3)C)C)C
Properties
C16H28O
Molar mass 236.399 g·mol−1
Density 0.939 g/cm3
Melting point 75 °C (167 °F; 348 K)
Boiling point 120 °C (248 °F; 393 K) (1.40 mm Hg)
insoluble
Solubility in ethanol soluble
1.48
Hazards
Flash point 161 °C (322 °F; 434 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.2 Ambroxide is used in perfumery for creating ambergris notes and as a fixative.2 Ambroxide has a scent with woody, musky and slightly salty nuances.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.2

Conversion of sclareol to ambroxide source ↗
References

References

  1. "Ambroxan (Registration #3195685)". trademarkia.com. Retrieved 25 February 2018.
  2. Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 72
  3. "Разница серой амбры и ноты амбры. Синтетические аналоги амбры". syntheticamber.ru. Retrieved 2025-09-11.
  4. George A. Burdock (2010), "1,5,5,9-TETRAMETHYL-13-OXATRICYCLO-(8.3.0.0(4,9)) TRIDECANE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, p. 1895
  5. "ambroxan". Scents and Flavors. Scents and Flavors. Retrieved 26 March 2026.
  6. Brian M Lawrence (2003). Essential Oils 1995-2000. Allured Pub. ISBN 0-931710-94-4.
  7. 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. S2CID 106394152.