Ambroxide

Ambroxide

Names
IUPAC name 3a,6,6,9a-Tetramethyldodecahydronaphtho-[2,1-b]furan
Other names Ambrox (Firmenich) Ambrofix (Givaudan) Ambroxan (Kao)[1] Ambermox Orcanox (3aR-(3aalpha,5abeta,9aalpha,9bbeta))-Dodecahydro-3a,6,6,9a-tetra-methylnaphtho(2,1-b)furan; Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-,; 8alpha, 12-Oxido-13,14,15,16-tetranorlabdane; 1,5,5,9-Tetramethyl-13-oxatricyclo(8.3.0.0(4,9))tridecane
Identifiers
CAS Number	6790-58-5 3738-00-9
ChEMBL	ChEMBL496447
ChemSpider	9032756
EC Number	229-861-2
Jmol interactive 3D	Image
PubChem	10857465
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	236.40 g·mol^−1
Density	0.939 g/cm^3
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).
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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]

Synthesis

Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage.^[3] Sclareol is oxidatively degraded to a lactone, which is hydrogenated to the corresponding diol, The resulting compound is dehydrated to form ambroxan:^[2]

Use

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.^[4]

References

1. http://www.trademarkia.com/ambroxan-78528957.html
2. Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 72
3. Essential Oils 1995-2000, Dr Brian M Lawrence, ISBN 0-931710-94-4
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