5560-99-6

Upstream product

• 79-77-6 (E)-β-ionone 
• 78108-48-2 2-lithio-1-trimethylsiloxyethylene 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 145572-39-0 1-bromo-4,4-diethoxy-2-methylbut-1-ene 
• 145572-38-9 1,2-dibromo-4,4-diethoxy-2-methylbutane 
• 54340-95-3 1,1-diethoxy-3-methyl-3-butene 
• 49817-16-5 β-apo-12-carotenol 
• 37384-77-3 ethyl β-ionylidene acetate 
• 180736-79-2 2-[3-(2,2-dimethoxy-ethyl)-buta-1,3-dienyl]-1,3,3-trimethylcyclohexene 
• 180736-80-5 (4E)-3-methylene-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-pentenal 
• 105175-91-5 3-methyl-5-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-penta-2,4-dienenitrile 
• 151018-50-7 1-bromo-4-ethoxy-2-methylbuta-1,3-diene 

Downstream Products

• 862098-80-4 6-Methyl-8-<1.3.3-trimethyl-cyclohexen-(1)-yl-(2)>-octatrien-(3.5.7)-on-(2) 
• 137046-92-5 4,6-Dimethyl-6-[(E)-2-(2,6,6-trimethyl-cyclohex-1-enyl)-vinyl]-cyclohexa-1,3-dienecarbaldehyde 
• 134962-99-5 4-Methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,6-dihydro-2H-pyran-2-ol 
• 77150-97-1 1-bromo-3-(β-ionilidene)-1-propene 
• 20638-88-4 retinonitrile 
• 84621-92-1 9-cis,13-cis-13-Desmethyl-13-methoxyretinsaeure-methylester 
• 80367-69-7 methyl (all E)-7-methyl-3-methoxy-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 67567-19-5 9-cis-β-ionylidenecrotonaldehyde 
• 6980-79-6 (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal 
• 564-87-4 (11Z)-retinal 
• 116-31-4 all-trans-Retinal 
• 86708-68-1 9-cis-13,14-dihydroretinoic acid ethyl ester 
• 86708-67-0 ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 
• 286372-76-7 4-Methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,6-dihydro-2H-pyran-2-ol 

Relevant academic research and scientific papers

Synthesis of isotopically labeled all-trans retinals for DNP-enhanced solid-state NMR studies of retinylidene proteins

Three all-trans retinals containing multiple 13C labels have been synthesized to enable dynamic nuclear polarization enhanced solid-state magic angle spinning NMR studies of novel microbial retinylidene membrane proteins including proteorhodpsi

Cyclofarnesoids and methylhexanoids produced from β-carotene in Phycomyces blakesleeanus

The oxidative cleavage of β-carotene in the Mucorales produces three fragments of 18, 15, and 7 carbons, respective heads of three families of apocarotenoids: The methylhexanoids, the trisporoids, and the cyclofarnesoids (named after their 1,6-cyclofarnes

Method for preparing vitamin A

The invention relates to a process for making vitamin A from ethynyl-retro-α-ionol using an allene acetate as intermediate.

Stereoselective syntheses of 13E and 13Z retinoic acids via a new intermediate C-15 β-methylenealdehyde

The methylene-de-oxo-bisubstitution reaction between dimethyl isopropylidene malonate and the C-15 β-methylenealdehyde 1 which could serve as substitute for E β-ionylideneacetaldehyde 2, produces stereoselectively the E,E olefin. Hence, new stereoselective syntheses of 13 E and 13 Z retinoic acids were described. (C) 2000 Elsevier Science Ltd.

Obtention of 2,2-(diethoxy) vinyl lithium and 2-methyl-4-ethoxy butadienyl lithium by Arene-catalysed lithiation of the corresponding chloro derivatives. Synthetic applications

Vinylic lithium reagents 1 and 2 could be obtained by the title procedure from their chloro precursors 5 and 6 instead of the less stable corresponding bromo derivatives 3 and 4. Condensation with carbonyl compounds leads to interesting synthetic applications such as a two steps synthesis of retinal 13 from β-cyclocitral 10.

A novel aldol condensation alternative: α,β-unsaturated aldehydes from 3-hydroxy-1-alkynes via dihydrodioxepins

The controlled aldol condensation between an aliphatic ketone and an acetaldehyde equivalent remains a challenge. One solution to this evergreen problem consists of the nucleophilic addition of acetylene to the ketone and the subsequent isomerization of the resulting 3-hydroxy-1-alkyne to the corresponding 2-alkenal. So far, however, the latter Step could only be executed with acid-insensitive substrates. We now present a milder, three-step method which extends the scope of the procedure considerably. In the first step, the 3-hydroxy-1-alkynes are converted into 2-propynyl ethylene glycol monoethers; these then undergo base-catalyzed cyclization to give the dihydro-1,4-dioxepins, which are hydrolyzed in acidic medium in the third and final step.

Polyvinylogation Reagents: 1-Lithio-4-trimethylsiloxy-penta-1,3-diene and 1-Lithio-4-ethoxy-2-methyl-buta-1,3-diene

Title products, lithiodienol ethers 6a and 7a, synthetic equivalents of 4-lithio pent-3-ene-2-one and 4-lithio-senecialdehyde were obtained by bromine-lithium exchange.They are choice reagents for the transformations 1 -> 2 and 1 -> 3, respectively.

Synthesis of three retinal models, including the 10-s-cis-locked retinal, all-E-12,19-methanoretinal

All-E-12,19-methanoretinal (1) is distinguished by the presence of the locked 10-s-cis conformation in the cyclohexadiene ring in the conjugated chain. 1 has been prepared together with its 13-Z isomer in an overall yield of 0.5percent. 1 and 13-Z-1 photochemically interconvert in a clean way.In this system, only photoisomerization around the C13=C14 double bond is observed.In the photostationary state, the 13-Z isomer is predominant.All-E-12-ethyl-19-methylretinal (2) and all-E-12-ethylretinal (3) were prepared in good overall yields (20percent and 30percent) from β-ionone using the novel synthon, 3-methyl-4-(diethylphosphono)-2-hexenenitrile (11).The photochemistry of these retinal derivatives is very similar to that of retinal.The 9-Z, 11-Z and 13Z isomers of 2 and 3 were photochemically prepared.The 13C NMR spectra of these new compounds gave information about the structural elements of alkyl groups in conjugated systems and about the conformation of the conjugated chain.