4176-94-7

Basic information

• Product Name: (1R,4aα,αR)-2,5,5,8aβ,α-Pentamethyl-2α,α-dihydroxydecalin-1β-butyric acid
• Synonyms: (1R,4aα,αR)-2,5,5,8aβ,α-Pentamethyl-2α,α-dihydroxydecalin-1β-butyric acid;(1R,4aα,αR)-Decahydro-α,2α-dihydroxy-α,2,5,5,8aβ-pentamethylnaphthalene-1β-butanoic acid;Sclareolic acid
• CAS NO: 4176-94-7
• Molecular Formula: C₁₉H₃₄O₄
• Molecular Weight: 326.47086
• Mol File: 4176-94-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,4aα,αR)-2,5,5,8aβ,α-Pentamethyl-2α,α-dihydroxydecalin-1β-butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4aα,αR)-2,5,5,8aβ,α-Pentamethyl-2α,α-dihydroxydecalin-1β-butyric acid(4176-94-7)
• EPA Substance Registry System: (1R,4aα,αR)-2,5,5,8aβ,α-Pentamethyl-2α,α-dihydroxydecalin-1β-butyric acid(4176-94-7)

Safety Data

• Hazardous Substances Data: 4176-94-7(Hazardous Substances Data)

Upstream product

• 144102-70-5 (13R,14R)-14-hydroperoxy-13,14-epoxy-15-norlabdan-8α-ol 
• 515-03-7 sclareol 
• 67-64-1 acetone 
• 122-52-1 triethyl phosphite 
• 143423-37-4 Phosphoric acid diethyl ester (3R,5aR,7aS,11aS,11bR)-3-hydroxy-3,5a,8,8,11a-pentamethyl-tetradecahydro-naphtho[2,1-b]oxepin-4-yl ester 
• 106462-14-0 sclareol 

Relevant articles and documents

Synthesis of (+)-drim-9(11)-en-8α-ol from sclareol

A drimane-type sesquiterpenoid, (+)-drim-9(11)-en-8α-ol, was synthesized from sclareol in four steps. The ozonolysis product of sclareol diacetate reacts with Cu(OAc)2·H2O to give 8α-acetoxy-14,15-bisnorlabdan-13-one. Photolysis of this compound followed by alkaline hydrolysis results in the target compound belonging to the normal steric series. (+)-Drim-9(11)-en-8α-ol acetate is highly unstable and decomposes during chromatography on SiO2.

Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids

A new chiral anisotropic reagent, phenylglycine methyl ester (PGME), developed for the elucidation of the absolute configuration of chiral α,α- disubstituted acetic acids, has turned out to be applicable to other substituted carboxylic acids, such as chiral α-hydroxy-, α-alkoxy-, and α- acyloxy-α,α-disubstituted acetic acids, as well as to chiral β,β- disubstituted propionic acids. Because a carboxylic moiety is convertible from other functional groups, e.g., ozonolysis of an olefin and oxidative cleavage of a glycol, the present findings can expand the utility of the PGME method to the absolute configuration determination of various types of organic compounds, even those which initially lack oxygen functions. Several examples of the combination of chemical reactions and the PGME method are described.

INVESTIGATION OF THE PRODUCTS OF THE OZONOLYSIS OF SCLAREOL AND THE PATHWAYS FOR THEIR FORMATION

It has been established that main products of the ozonolysis of sclareol (I) under various conditions are "sclareol oxide" (III), 8α-hydroxy-14,15-bisnorlabdan-13-one (IV), and the new compound (13R,14R)-14-hydroperoxy-13,14-epoxy-14-norlabdan-8α-ol (X), and structure of which has been shown on the basis of its trans-formations.The acid fraction of the ozonation products, the yield of which was low (8percent) included two compounds: sclareolic acid (85percent) and 18α-hydroxy-14,15,16-trisnorlabdan-13-oic acid (3percent).The mechanism for the formation of the above mentioned compounds is discussed.