Sclareol

A simple approach to sclareol oxide has also been reported [114]. 

Scintillation detector, 26 420, 433-434 SCISS P-Scission reactions, 24 280-281 SCK micelles, 20 489, 490 Sclareol, 24 573 Sclareolide, 24 573 Sclerenchyma cells, 22 18 Scleroglucan, 20 578, 4 724t... 

The fragrance (-)-Ambrox (a commercial substitute for ambergris from the blue sperm whale) was made by oxidation of (-)-sclareol (1) with RuClj/aq. Na(IO )/ CC1 -CH3CN/40°C a mixture of (+)-sclareolide (2) with the (-)-acetoxy acid... 

Trade Names. Compound starting from natural sclareol Ambermore (Aromor), Ambrox (Firmenich), Ambroxan (Cognis), Ambroxid (H R) compound starting from homofarne-senic acid derivatives Ambrox DL (Firmenich), Synambrane (FI R) compound starting from 2-methyl-4-(2,6,6-trimethylcyclohex-l(2)enyl)-2-butenal Cetalox (Firmenich). 

In addition to linalyl acetate, the oil contains linalool and other terpene alcohols, as well as their acetates. When the volatile components are evaporated, a distinct ambergris note develops that is attributed to oxidative degradation products of sclareol [515-03-7] [746-750a]. Sclareol is the main component in the concrete, obtained by solvent extraction of S. sclarea L. leaves [750b]. 

Sclareol is used as a starting material for a number of ambergris fragrances. Major cultivation areas for S. sclarea L. are Russia, the Mediterranean countries, and the United States. 

Sclareol 114 (Structure 4.35), a ditertiary glycol, is a constituent of clarysage Salvia sclarea) oil [56, 57]. The diterpene ketone sclareolide 115 and the lactone ambrox 116 are important (bio)synthetic derivatives found in clarysage extract. 

The aerial parts of Conyza steudellii (Asteraceae) have given new labdane xylosides, while from the leaves of Conyza trihecatactis, a xylopyranoside of 13-epi-sclareol has been isolated among other labdanes [104,105]. Havardic acids A-F (as methyl esters), have been isolated from another genus of the Asteraceae family, i.e Grindelia havardii [106]. 11-oxo-manoyl oxide derivatives and coleosol, which is also a manoyl oxide derivative, have been obtained from Coleus forskohlii (Labiateae) [107,108] while from another plant of the Labiatae family, Roylea calycina a tumor inhibitory compound, namely precalyone, as well as calyone have been isolated [109]. 

The absolute configurations of sclareol (2) and manool (5), Fig. (7), at C-13 have been determined [133]. As Hanson reported [134], the absolute stereochemistry assigned to some labdanes should be reexamined due to the enantiomers of labdanes. The biosynthetic pathways of sclareol and manool start from a geranyllinalool - type skeleton which cyclizes in a similar fashion as that described for cativic acid [135] and, via the intermediate 6, Fig. (7), sclareol is formed by hydration of 6, or manool by the loss of a proton [112,136]. 

Manoyl oxide (4), Fig. (7), has been isolated as a pure compound or identified via analytical techniques, in several plant species [33,44,63,137, 138,139]. Ohloff has shown that manoyl oxide can be prepared from sclareol [140]. The physical and chromatographic data of the synthetic and of the natural manoyl oxides have been compared and discussed [141]. Hodges and Reed have substantially contributed to the knowledge of the stereochemistry of manoyl oxide [141]. 

Data submitted for publication. The study concerns the effect of the thiomidazolide derivative of enf-3p-hydroxy manoyl oxide and of sclareol on the expression of the two oncogenes in two leukemic cell lines, where an apoptotic effect was also observed... 

Sclareol glycol, a derivative of sclareol exhibited antihypoxic effects in mice [247] and also induced changes in core body temperature by interacting with dopamine receptors in rats [248]. 

IFRA provides specifications for purity regarding the following fragrance materials Allyl esters, Cade oil rectified, Famesol, Hexylidene cyclopentanone, Nootkatone, Sclareol, and Oils of the Pinacea species. 

Show a mechanism for the formation of sclareol from geranylgeranyl pyrophosphate. 

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