Ambroxan

• ( 3aR, 5as, 9aS, 9bR ) -3a, 6,6,9 a -tetramethyl- dodecahydronaphto [2,1- b] furan
• (-)- Ambrox
• (-)- Ambroxan
• (-)- Ambroxid

• 6790-58-5 [(-) - Ambrox ]
• 100679-85-4 [( ±)- Ambrox ]
• 3738-00-9 [ stereoisomer ]
• 68365-89-9 [(-) -epi- Ambrox ]

White solid with a characteristic odor

Fixed [( -)- ambrox ]

0.939 g · cm -3, [(-) - Ambrox ]

75 ° C ( 760 mm Hg), [(-) - Ambrox ]

120 ° C [ (-)- Ambrox ]

• Slightly soluble in water [( -)- ambrox ]
• Soluble in ethanol [(-) - Ambrox ]

Template: Infobox chemical / molecular formula search available

Ambrox (also ambroxan ) is a chemical compound from the class of Tetranlabdanoxide. As the source previously served Ambra, which occurs in the intestines of whales. Ambrox is considered one of the most valuable animal scents next civet and musk.

Occurrence

Ambrox produced by the reaction of Ambrein (main constituent of ambergris, a waxy substance from the digestive tract of sperm whales ) with atmospheric oxygen. In small amounts ambrox also comes in the following sources:

• Absolue of tobacco (Nicotiana tabacum )
• In the oil of clary sage (Salvia sclarea )
• In the rock rose (Cistus labdaniferus )
• And in the cypress (Cupressus sempervirens)

Production and representation

To obtain ambrox Ambrein is no longer used, it is replaced as the starting material by sclareol from Salvia sclarea. Through the publication of the first partial synthesis in 1950 by the company Firmenich an alternative ambrox source was found. The key step in the industrial synthesis is the oxidative degradation of the side chain with chromium trioxide CrO3. The subsequent reduction of the lactone with lithium aluminum hydride leads to the diol, which is cyclized in the presence of acids to the desired ether. As a byproduct which is thermodynamically more stable 9b -epi- Ambrox can occur. The reaction can be carried out on an industrial scale with a yield of 54%.

After the expiry of the patent in the early 1980s more technically feasible synthetic routes have been published. A decomposition reaction of sclareol using sodium periodate ( instead of potassium permanganate ) was published in the group of Sir Derek HR Barton and patents pending.

Although the synthesis steps can be performed relatively easily and safely, is the major drawback in these syntheses in the fluctuating supply situation and thus widely varying prices of sclareol.

As an alternative to sclareol may also ( )-cis- abienol be used for the preparation of ambrox. ( )-cis- abienol is obtained from Canada balsam.

By ozonolysis of ( )-cis- abienol and subsequent reductive workup to give a diol, which can be cyclized in pyridine with excellent yields of ambrox with tosyl chloride. In addition to this synthetically considered especially skillful degradation reaction can ambrox of a number of other natural products [- thujone or ( )- carvone - (- ) - Drimenol, ()] also starting to be won.

Use and characteristics

Ambrox is a well known since ancient times perfume, which is used in perfumery.

The different stereoisomers of ambrox have a similar scent, but differ in their odor thresholds.

The annual world production for ambrox and analogues is just over 30 tons.

Trade names

• Ambro, Ambroxan, Amberlynx: (-) -enantiomer
• Cetalox: racemate