Ambroxide

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Ambroxide
Ambrox.svg
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.147
EC Number 229-861-2
UNII
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
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[edit]

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]

Ambroxide synthesis sclareol.svg

Use[edit]

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[edit]

  1. ^ http://www.trademarkia.com/ambroxan-78528957.html
  2. ^ a b c 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