26289-05-4

Usage

Uses

Used in Organic Chemistry:
3-Buten-2-one,4-[(1S,2R,4S)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]-, (3S)is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure and functional groups make it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3-Buten-2-one,4-[(1S,2R,4S)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]-, (3S)is used as a key component in the development of new drugs. Its specific stereochemistry and functional groups can be leveraged to design molecules with targeted biological activities, potentially leading to the discovery of new therapeutic agents.
Used in Material Science:
3-Buten-2-one,4-[(1S,2R,4S)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]-, (3S)may also find applications in the field of material science. Its unique structure could be utilized in the development of new materials with specific properties, such as advanced polymers, coatings, or composites with tailored characteristics for various industrial applications.

Upstream product

• 3351-86-8 fucoxanthin 
• 130224-16-7 (1'R,2'R)-4-(2'-hydroxy-2',6',6'-trimethyl-4'-oxocyclohexyliden)but-3-en-2-on 
• 22451-58-7 (1'R,2'R,4'R)-4-(4'-acetoxy-2'-hydroxy-2',6',6'-trimethylcyclohexyliden)but-3-en-2-on 

Downstream Products

• 22451-58-7 (1'S,2'R,4'R)-4-(4'-acetoxy-2'-hydroxy-2',6',6'-trimethylcyclohexyliden)but-3-en-2-on 
• 130321-04-9 (1'S,2'R,4'S)-4-(4'-Acetoxy-2'-hydroxy-2',6',6'-trimethylcyclohexyliden)but-3-en-2-on 

Relevant academic research and scientific papers

Chemical cleavage of fucoxanthin from Undaria pinnatifida and formation of apo-fucoxanthinones and apo-fucoxanthinals identified using LC-DAD-APCI-MS/MS

As the most abundant carotenoid in nature, fucoxanthin is susceptible to oxidation under some conditions, forming cleavage products that possibly exhibit both positive and negative health effects in vitro and in vivo. Thus, to produce relatively high amounts of cleavage products, chemical oxidation of fucoxanthin was performed. Kinetic models for oxidation were probed and reaction products were identified. The results indicated that both potassium permanganate (KMnO4) and hypochlorous acid/hypochlorite (HClO/ClO?) treatment fitted a first-order kinetic model, while oxidation promoted by hydroxyl radical (OH) followed second-order kinetics. With the help of liquid chromatography–tandem mass spectrometry, a total of 14 apo-fucoxanthins were detected as predominant cleavage products, with structural and geometric isomers identified among them. Three apo-fucoxanthinones and eleven apo-fucoxanthinals, of which five were cis-apo-fucoxanthinals, were detected upon oxidation by the three oxidizing agents (KMnO4, HClO/ClO?, and OH).

Degradation of fucoxanthin to elucidate the relationship between the fucoxanthin molecular structure and its antiproliferative effect on caco-2 cells

Fucoxanthin has an antiproliferative effect on cancer cells, but its detailed structure–activity correlation has not yet been elucidated. To elucidate this correlation, fucoxanthin was degraded by ozonolysis. The degraded compounds of fucoxanthin obtained by ozonolysis were purified by HPLC and analyzed by NMR. The polyene chain of fucoxanthin was cleaved by ozonolysis, and the fucoxanthin was divided into two types of cyclohexyl derivatives, one with a β,γ-epoxy ketone group and the other with an allenic bond. In order to elucidate the structure–activity correlation, Caco-2 cells (human colorectal carcinoma) were treated with fucoxanthin degradation compounds. It was found that the entire structure of fucoxanthin is not essential for its antiproliferative effect and that even a partial structure exerts this effect.

Carotenoids and Related Polyenes. Part 2. Photoisomerization of an Allenic Carotenoid, Peridinin, and Allenic Model Compounds

Iodine-catalysed photoisomerization of peridinin 1a gave the novel (6S)-allenic isomer 1b whose structure was confirmed by chemical synthesis.In addition, the photochemical behaviour of several model compounds having a part structure of allenic carotenoid

72. Synthesis of Optically Pure Grasshopper Ketone and its Diastereoisomers and Related Compounds

Starting from our previously described synthon 1, the synthesis of four enantiomerically pure grasshopper ketons (diastereoisomeric 4-(2',4'-dihydroxy-2',6',6'-trimethylcyclohexylidene)but-3-en-2-ons) and of their oxo derivatives was performed.Spectral an

CHIRALITY OF PERIDININ AND DINOXANTHIN

Details are reported for the configurational assignment of peridinin as 3S, 5R, 6R, 3'S, 5'R, 6'S including ozonolytic degradation of its p-bromobenzoate to derivatives of known chirality obtained from fucoxanthin and violaxanthin.Details regarding derivatization and CD correlations in favour of the same chirality for dinoxanthin = neoxanthin 3-acetate are given.Key Word Index - Dinoflagellate carotenoids; chirality; peridinin; dinoxanthin.

Mimulaxanthin, the Main Carotenoid in Lamium montanum, Determination of its Absolute Configuration. Absolute Configuration of Deepoxyneoxanthin by its Correlation with Neoxanthin

The carotenoid mixture isolated from the yellow flowers of Lamium montanum PERS. (Labiatae) consists of more than 75percent of carotenoids with allenic end groups.Besides 32percent of neoxanthin/neochrome we isolated 44percent of mimulaxanthin (1a), a very rare carotenoid so far only found in Mimulus sp. (Scrophulariaceae).Its absolute configuration was determined by oxidative degradation to the known ketone 3 ("grasshopper ketone") and by spectroscopic and chiroptical comparisons with neoxanthin (6).Mimulaxanthin (1a) therefore is (3S,5R,6R,3'S,5'R,6'R)-6,7,6',7'-tetradehydro-5,6,5',6'-tetrahydro-β,β-carotene-3,5,3',5'-tetraol.Deepoxyneoxanthin, which was reisolated from Mimulus sp. is (3S,5R,6R,3'R)-6,7-didehydro-6,7-dihydro-β,β-carotene-3,5,3'-triol (2), as shown by spectroscopic and chemical correlation with neoxanthin (6; de-epoxydation by BuLi/FeCl3).