Ambroxide
Names | |
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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 | |
6790-58-5 3738-00-9 (unspecified stereochemistry) | |
3D model (Jmol) | Interactive image |
ChEMBL | ChEMBL496447 |
ChemSpider | 9032756 |
ECHA InfoCard | 100.027.147 |
EC Number | 229-861-2 |
PubChem | 10857465 |
UNII | TD34B3O8M9 |
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Properties | |
C16H28O | |
Molar mass | 236.40 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 |
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]
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
- ↑ http://www.trademarkia.com/ambroxan-78528957.html
- 1 2 3 Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 72
- ↑ Essential Oils 1995-2000, Dr Brian M Lawrence, ISBN 0-931710-94-4
- ↑ 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
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