6980-79-6

Basic information

• Product Name: (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal
• Synonyms: (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal
• CAS NO: 6980-79-6
• Molecular Weight: 244.377
• Mol File: 6980-79-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal(6980-79-6)
• EPA Substance Registry System: (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal(6980-79-6)

Safety Data

• Hazardous Substances Data: 6980-79-6(Hazardous Substances Data)

Upstream product

• 53018-97-6 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal 
• 472-80-0 beta-Ionol 
• 62924-18-9 β-ionylidene-acetonitrile 
• 72214-33-6 3-(2,6,6-Trimethylcyclohex-1-enyl)prop-2-enenitrile 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 58526-71-9 (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal 
• 74109-37-8 ethyl (2E,4E,6E)-5-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6-hepta-trienoate 
• 59955-09-8 (Β-Ionyliden-aethyliden)-acetonitril 
• 5299-98-9 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienenitrile 
• 79-77-6 (E)-β-ionone 
• 105175-91-5 3-methyl-5-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-penta-2,4-dienenitrile 
• 14398-57-3 5-methyl-7t-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2t,4t,6-trienoic acid methyl ester 
• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 

Downstream Products

• 6488-41-1 Cyan-<β-ionyliden-aethyliden>-essigsaeure 
• 67567-19-5 9-cis-β-ionylidenecrotonaldehyde 
• 107508-18-9 7-cis-β-ionylidenecrotonaldehyde 
• 669772-25-2 ethyl 13-demethyl-13-hydroxy-13,14-dihydroretinoate 
• 129165-44-2 (2E,4E,6E,8E)-7-methyl-9-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-nona-2,4,6,8-tetraenenitrile 
• 20638-88-4 retinonitrile 
• 99302-31-5 retinal 
• 99302-30-4 retinal 
• 116-31-4 all-trans-Retinal 
• 1220-77-5 6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 129165-50-0 (13-²H)13-demethylretinal 
• 129261-66-1 (13-²H)13-demethylretinal 
• 129165-55-5 (13-²H)-5-methyl-7-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6-heptatrienal 
• 24336-20-7 7-methyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenal 

Relevant articles and documents

Electrocyclized retinal

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Expansion of first-in-class drug candidates that sequester toxic all-trans-retinal and prevent light-induced retinal degeneration

All-trans-retinal, a retinoid metabolite naturally produced upon photoreceptor light activation, is cytotoxic when present at elevated levels in the retina. To lower its toxicity, two experimentally validated methods have been developed involving inhibition of the retinoid cycle and sequestration of excess of all-trans-retinal by drugs containing a primary amine group. We identified the first-in-class drug candidates that transiently sequester this metabolite or slow down its production by inhibiting regeneration of the visual chromophore, 11-cis-retinal. Two enzymes are critical for retinoid recycling in the eye. Lecithin:retinol acyltransferase (LRAT) is the enzyme that traps vitamin A (all-trans-retinol) from the circulation and photoreceptor cells to produce the esterified substrate for retinoid isomerase (RPE65), which converts all-trans-retinyl ester into 11-cis-retinol. Here we investigated retinylamine and its derivatives to assess their inhibitor/substrate specificities for RPE65 and LRAT, mechanisms of action, potency, retention in the eye, and protection against acute light-induced retinal degeneration in mice. We correlated levels of visual cycle inhibition with retinal protective effects and outlined chemical boundaries for LRAT substrates and RPE65 inhibitors to obtain critical insights into therapeutic properties needed for retinal preservation.

Polyenylidene thiazolidine derivatives with retinoidal activities

Several polyenylidene thiazolidinedione or 2-thioxo-4-thiazolidinone derivatives were synthesized and their retinoidal activities were examined in terms of the differentiation-inducing ability towards human promyelocytic leukemia HL-60 cells and inhibitory effect on interleukin (IL)-1α-induced IL-6 production in MC3T3-E1 cells. Compounds containing a trimethylcyclohexenyl ring induced HL-60 cell differentiation with weaker activity than retinoic acid (1a) by one or two orders of magnitude. The thiazolidinedione derivatives (2, 5, 7) showed stronger activity than the corresponding 2-thioxo-4-thiazolidinone derivatives (3, 6, 8). The effects of a retinoid antagonist (LE540) and synergists (retinoid X receptor (RXR) agonists, HX600 or HX630) on the activities of thiazolidine derivatives indicate that these compounds elicit their activities through the nuclear retinoic acid receptors (RARs). All the thiazolidines examined also inhibited IL-1α-induced IL-6 production with IC50 values of 10nM order. The retinoidal activities of the thiazolidines are significant, considering that replacement of the carboxylic acid in retinoid structures with bioisosteric functional groups is generally ineffective, as seen in the structure-activity relationships of retinoidal benzoic acids.