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Ambroxide

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(Redirected from Ambroxan) Chemical compound
Ambroxide
Names
Preferred IUPAC name (3aR,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyldodecahydronaphthofuran
Other names Ambrox (Firmenich)
Ambrofix (Givaudan)
Ambroxan (Kao)
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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.027.147 Edit this at Wikidata
EC Number
  • 229-861-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: YPZUZOLGGMJZJO-LQKXBSAEBI
  • 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
SMILES
  • CC1(CCC2(1CC3(2CCO3)C)C)C
Properties
Chemical formula C16H28O
Molar mass 236.399 g·mol
Density 0.939 g/cm
Melting point 75 °C (167 °F; 348 K)
Boiling point 120 °C (248 °F; 393 K) (1.40 mm Hg)
Solubility in water insoluble
Solubility in ethanol soluble
Refractive index (nD) 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 , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

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. Small amounts (< 0.01 ppm) are used as a flavoring in food.

Synthesis

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

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. Allured Pub. 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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