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.[2] Ambroxide is used in perfumery for creating ambergris notes and as a fixative.[2] Small amounts (< 0.01 ppm) are used as a flavoring in food.[3]

Ambroxide
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
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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Infobox references

Synthesis

Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage.[4] Sclareol is oxidatively degraded to a lactone, which is hydrogenated to the corresponding diol.[5] The resulting compound is dehydrated to form ambroxide.[2]

Conversion of sclareol to ambroxide

References
  1. "Apply for a Trademark. Search a Trademark". 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. 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
  4. Brian M Lawrence (2003). Essential Oils 1995-2000. ISBN 0-931710-94-4.
  5. 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.
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