869476-96-0

Basic information

• Product Name: [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester
• Synonyms: [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester
• CAS NO: 869476-96-0
• Molecular Weight: 346.423
• Mol File: 869476-96-0.mol

Chemical Properties

• CAS DataBase Reference: [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester(869476-96-0)
• EPA Substance Registry System: [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester(869476-96-0)

Safety Data

• Hazardous Substances Data: 869476-96-0(Hazardous Substances Data)

Upstream product

• 869476-95-9 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 951377-85-8 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl ester 
• 96013-75-1 2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol 
• 595581-64-9 (3aR,6aR)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 683276-43-9 (4R,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)prop-2-en-1-ol 
• 951377-84-7 (3aR,6aS)-6-Methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 129263-68-9 ((3aS,4R,6aS)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 869476-94-8 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid methyl ester 
• 869476-93-7 ((3aR,5S,6aR)-2,2-dimethyl-4-oxotetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl)acetic acid methyl ester 

Downstream Products

• 944340-53-8 [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester 
• 289030-99-5 Oleocanthal 
• 951378-02-2 (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester 

Relevant articles and documents

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides methods of synthesizing the purified enantiomers of oleocanthal. The invention further provides methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues

(Chemical Equation Presented) Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.

COMPOUNDS AND DERIVATIVES FOR THE TREATMENT OF MEDICAL CONDITIONS BY MODULATING HORMONE-SENSITIVE LIPASE ACTIVITY

The present invention discloses compounds that are inhibitors of hormone-sensitive lipase. The present invention also discloses the use of the compounds and derivatives to inhibit hormone-sensitive lipase, various pharmaceutical compositions including the compounds, and methods of treatment using these compounds and compositions.

Synthesis and assignment of absolute configuration of (-)-oleocanthal: A potent, naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils

(Chemical Equation Presented) Effective total syntheses and the assignment of absolute configurations of both the (+)- and (-)-enantiomers of oleocanthal 1 (a.k.a. deacetoxy ligstroside aglycon), the latter derived from extra virgin olive oils and known to be responsible for the back of the throat irritant properties of olive oils, have been achieved. The absolute and relative stereochemistry of the naturally occurring enantiomer (-)-1 proved to be 3S,4E. Both syntheses begin with D-(-)-ribose, proceed in 12 steps, and are achieved with an overall yield of 7%. Both enantiomers proved to be non-steroidal anti-inflammatory and anti-oxidant agents.