80922-54-9

Upstream product

• 18049-09-7 ethyl (2E,4E)-5,9-dimethyldeca-2,4,8-trienoate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 64-17-5 ethanol 
• 14393-45-4 (E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid 
• 42520-11-6 1,1-diethoxy-2-bromo-ethene 

Downstream Products

• 14393-44-3 (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)prop-2-en-1-ol 
• 14393-46-5 methyl (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylate 
• 38818-52-9 (Z)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)prop-2-en-1-ol 
• 69258-08-8 (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride 
• 53291-87-5 methyl (Z)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylate 
• 14393-45-4 (E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid 
• 52209-30-0 (E)-N,N-dimethyl-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylamide 
• 1259012-84-4 (E)-N-methyl-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylamide 
• 100251-74-9 (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylamide 

Relevant academic research and scientific papers

Synthesis of one double bond-inserted retinal analogs and their binding experiments with opsins: Preparation of novel red-shifted channelrhodopsin variants

In optogenetics, red-shifted channelrhodopsins (ChRs) are eagerly sought. We prepared six kinds of new chromophores with one double bond inserted into the polyene side chain of retinal (A1) or 3,4-didehy-droretinal (A2), and examined their binding efficie

Photocatalytic e → Z Isomerization of β-Ionyl Derivatives

An operationally simple E → Z isomerization of activated dienes, based on the β-ionyl motif intrinsic to retinal, is reported using inexpensive (-)-riboflavin (vitamin B2) under irradiation at 402 nm. Selective energy transfer from photoexcited (-)-riboflavin to the starting E-isomer enables geometrical isomerization. Since the analogous process with the Z-isomer is inefficient, microscopic reversibility is circumvented, thereby enabling a directional isomerization to generate the contra-thermodynamic product (up to 99% yield, up to 99:1 Z/E). Prudent choice of photocatalyst enables chemoselective isomerization to be achieved in both inter- and intramolecular systems. The principles established from this study, together with a molecular editing approach, have facilitated the development of a regioselective isomerization of a truncated triene based on the retinal scaffold.

OFF-NOTE BLOCKING SENSORY ORGANIC COMPOUNDS

Disclosed are Compounds that block off-notes in consumables and methods of blocking off-notes in consumables including off-notes provided by artificial sweeteners including aspartame, Saccharin, acesulfame K (Acesulfame potassium), sucralose and cyclamate; and including stevioside, swingle extract, glyccerhizin, perillartine, naringin dihydrochalcone, neohesperidine dihydrochalcone, mogroside V, rubusoside, rubus extract, and rebaudioside A.

ANTINEOPLASTIC AND CURCUMIN DERIVATIVES AND METHODS OF PREPARATION AND USE

This invention comprises antineoplastic curcumin derivatives and methods of preparation and use thereof. Note is made of the acylation product of the lithium enolate of β-ionone using the acid chloride, 2(E)-3-(2,6,6-trimethycyclohex-1-en-1-yl)propenoyl chloride derived from β-cyclocitral. Particular reference is made to the isomeric compound, 1-(2,6,6-trimethylcyclohex-2-en-1-yl)-7-(2,6,6-trimethylcyclohex-1-en-1-yl)- 1,6-heptadiene-3,5-dione.

Retinoids and related compounds. Part 22. Synthesis of β-ionone analog tricarbonyliron complexes

The synthesis of β-ionone analog tricarbonyliron complexes was investigated. N-Methoxy-N-methyl-(2,6,6-trimethyl-1-clohexen-1-yl)-2- propenamide (Weinreb amide), prepared from the corresponding ethyl ester and N,O-dimethylhydroxylamine hydrochloride, reacted smoothly with various organometallic reagents to afford the β-ionone analogs in good to excellent yields. Treatment of these compounds with dodecacarbonyltriiron afforded the corresponding tricarbonyliron complexes in high yields.

Lewis Acid-Catalyzed Intramolecular [2 + 2] Cycloaddition of α-Ester-Substituted Conjugated Dienyl- And Trienylphosphonates. New Synthesis of Functionalized Cyclic Terpenoids

α-Ester-substituted 1,3-dienylphosphonates 7 and 8, prepared by the Knoevenagel condensation, underwent intramolecular [2 + 2] cycloaddition in the presence of Lewis acid to form bicyclo[4.2.0] (26-57% yield) and bicyclo[3.2.0]skeleton (14-38% yield), respectively. Similar treatment of homologous 1,3-dienylphosphonate 11 and 1,3,5-trienylphosphonate 12 resulted in the formation of ionone derivatives (30-94% yield). The intramolecular cycloaddition reaction was applicable to several conjugated dienes bearing an ester group.

2,2-Di(ethoxy)vinyllithium: Reactions with carbonyl compounds

2,2-Di(ethoxy)vinyllithium 2 generated from bromo ketene acetal 1 reacts with carbonyl compounds to give either β-hydroxy esters 5 or conjugated esters 6 or hydroxy ketene acetals 7 according to the work up.

Synthesis of Hydroxy-γ-lactones from α,β-Unsaturated Aldehydes

According to Scheme 1 the α,β-unsaturated aldehydes 3-9 react in three steps (epoxidation, PO olefination, and selective hydrogenation) to give the epoxy esters 36-42.Generally, these steps are interchangeable, predominantly the epoxidation and olefination.Thus, the epoxy acid esters 26-32 are synthesized via the epoxides 10-16 or via the dienoic esters 17-23.Homogeneously catalyzed hydrogenation of 26-31 gives the saturated esters 36-41.In case this reaction fails (e.g. with 32), sequence e, g (Scheme 1) via γ,δ-unsaturated esters (e.g. 35) might be successful.All these α,β-unsaturated esters 17-23 and 26-32 possess (E) configuration.Even the reaction of 3 or 6 with the propionate 2 leads to the (E) esters 24 or 25, respectively.Hydrolysis of the epoxy acid esters 36-41 gives the hydroxy-γ-lactones 43-48.