Ambroxide

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); 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	100679-85-4 ; 3738-00-9 (unspecified stereochemistry) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:78307;
ChEMBL	ChEMBL496447 ;
ChemSpider	9032756 ;
ECHA InfoCard	100.027.147
EC Number	229-861-2;
PubChem CID	10857465;
UNII	K60YJF1E9A ;
CompTox Dashboard (EPA)	DTXSID0047113 ;
	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/s1 Key: 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(CCC[C@]2([C@H]1CC[C@@]3([C@@H]2CCO3)C)C)C;
Properties
Chemical formula	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)
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 [77 °F], 100 kPa). (what is ?) Infobox references

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]

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]

References

^ "Apply for a Trademark. Search a Trademark". trademarkia.com. Retrieved 25 February 2018.
^ ^a ^b ^c Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 72
^ 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
^ 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. S2CID 106394152.

[1] "Apply for a Trademark. Search a Trademark". trademarkia.com. Retrieved 25 February 2018.

[perf-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.

[Gordon-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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