Sclareol

• Labd -14- ene- 8 ,13 -diol

Fixed

95-100 ° C.

218-220 ° C ( 19 mmHg)

• > 5000 mg · kg -1 ( LD50, rat, oral)
• > 5000 mg · kg -1 ( LD50, Rabbit, transdermal)

Template: Infobox chemical / molecular formula search available

Sclareol is a naturally occurring bicyclic diterpene alcohol ( terpenoid ). Sclareol owns the carbon backbone of the labdane diterpene; the bicyclic core consists of two fused cyclohexane rings. The amber- colored solid has a sweet, balsamic scent.

Production and representation

(-)- Sclareol can be obtained by conventional steam distillation of clary sage (Salvia sclarea ). 2010, the enzymatic pathway for the biological synthesis was published. Sometimes this also an alternative manufacturing process was presented, which describes the expression of sclareol from genetically modified E. coli bacteria. This results in addition to the desired (-)- 13 -epi- sclareol also sclareol which can be removed by gas chromatography.

The ( ) enantiomer of sclareol can be obtained by extraction from Conyza trihecatactis.

Use and characteristics

Sclareol is used as a fragrance in cosmetics and perfumes and as a flavoring in food. Especially for the alternative synthesis of ambrox (instead of Ambrein ) comes sclareol used.

The key step in the industrial synthesis is the oxidative degradation of the side chain by oxidation with chromium trioxide CrO3. The subsequent reduction of the lactone with lithium aluminum hydride leads to the diol which in acidic medium to the desired cyclized ether. As a byproduct which is thermodynamically more stable 9b -epi- Ambrox can occur. The reaction can be carried out on a large scale with a yield of 54%.

Sclareol induces apoptosis in human leukemia cells and colon tumor cells. The occurrence of cell death is time-and dose-dependent.