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Names | |
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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 | |
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3D model (
JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.027.147 |
EC Number |
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PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
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) |
insoluble | |
Solubility in ethanol | soluble |
Refractive index (nD)
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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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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 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]