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
CAS Number	100679-85-4 Y 3738-00-9 (unspecified stereochemistry) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:78307
ChEMBL	ChEMBL496447 Y
ChemSpider	9032756 Y
ECHA InfoCard	100.027.147
EC Number	229-861-2
PubChem CID	10857465
UNII	K60YJF1E9A Y
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 Y 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
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). N (what is YN ?) 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