67567-19-5

Basic information

• Product Name: 7-(2,2,6-trimethylcyclohexen-1-yl)-5-methyl-2,4,6-heptatrienal
• Synonyms: 7-(2,2,6-trimethylcyclohexen-1-yl)-5-methyl-2,4,6-heptatrienal
• CAS NO: 67567-19-5
• Molecular Formula: C₁₇H₂₄O
• Molecular Weight: 244.37
• Mol File: 67567-19-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-(2,2,6-trimethylcyclohexen-1-yl)-5-methyl-2,4,6-heptatrienal(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(2,2,6-trimethylcyclohexen-1-yl)-5-methyl-2,4,6-heptatrienal(67567-19-5)
• EPA Substance Registry System: 7-(2,2,6-trimethylcyclohexen-1-yl)-5-methyl-2,4,6-heptatrienal(67567-19-5)

Safety Data

• Hazardous Substances Data: 67567-19-5(Hazardous Substances Data)

Upstream product

• 107508-18-9 7-cis-β-ionylidenecrotonaldehyde 
• 14398-58-4 (2E,4Z,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trien-1-ol 
• 62924-18-9 β-ionylidene-acetonitrile 
• 72214-33-6 3-(2,6,6-Trimethylcyclohex-1-enyl)prop-2-enenitrile 
• 472-80-0 beta-Ionol 
• 53018-97-6 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal 
• 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 
• 187339-53-3 (2E,4Z,6E)-7-(1-Hydroxy-2,2,6-trimethyl-cyclohexyl)-5-methyl-hepta-2,4,6-trienoic acid methyl ester 
• 187339-52-2 (2Z,4E)-3-methyl-5-(1-hydroxy-2,2,6-trimethylcyclohexyl)-pent-2,4-dien-1-al 
• 187409-93-4 1-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol 
• 187339-51-1 (2Z,4E)-3-methyl-5-(1-hydroxy-2,2,6-trimethylcyclohexyl)-pent-2,4-dien-1-ol 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 

Downstream Products

• 6980-79-6 (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal 
• 107508-18-9 7-cis-β-ionylidenecrotonaldehyde 
• 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 
• 187339-59-9 methyl-(2E,4E,6Z,8E)-3-³H₃C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate 
• 187339-58-8 C₂₁H₂₇⁽²⁾H₃O₂ 
• 187339-57-7 (2E,4Z,6E)-1-³H₃C,5-methyl-7-(2,2,6-trimethylcyclohex-1-enyl)-hepta-2,4,6-triene-1-one 
• 187339-56-6 C₁₈H₂₃⁽²⁾H₃O 
• 58526-50-4 [7t,9c,11t,13t]retinoic acid methyl ester 
• 302-79-4 9-cis-retinoic acid 
• 187339-55-5 (2E,4Z,6E)-1-³H₃C,5-methyl-7-(2,2,6-trimethylcyclohex-1-enyl)-hepta-2,4,6-triene-1-ol 

Relevant articles and documents

A synthesis method of 9-cis Beta-carotene

The present invention relates to a method for synthesizing 9 - cis Beta-carotene (9 - cis beta-carotene) compounds having high purity and easy mass production through a chemical reaction, and a reaction for substituting 9 - cis Retinol groups of Alcohol with 9 - cis Phosphonium salt. The reaction of β - (3 - Methyl-2-butenal to Knoevenagel condensation) to synthesize All-trans Aldehyde. In step 9 - cis Retinoic Phosphonium salt) and in step), the completed All-trans Aldehyde is subjected to Wittig Olefination reaction with carbon double bonds, and 9. cis Beta-carotene obtained by the reaction of carbon double bonds.

Synthesis of 9-cis-retinoic acid and C-20-[3H3C]-9-cis-retinoic acid with high specific activity

The synthesis of 9-cis-retinoic acid starting from 2,2,6-trimethylcyclohexanone is described. The same methodology was extended for the synthesis of deuterium and tritium labeled 9-cis-retinoic acid with high specific activity (73 Ci/mmol). In this methodology, a Grignard reaction was utilized for introducing three tritium atoms simultaneously in the final synthetic steps.

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.

Dependence of the Triplet Potential of Retinal Homologues on the Chain Length: Resonance Raman Spectroscopy and Analysis of Triplet-Sensitized Isomerization

The Raman spectra of triplet species produced from the all-trans, 7-cis and 9-cis isomers of β-ionylideneacetaldehyde (C15 aldehyde) and of β-ionylidenecrotonaldehyde (C17 aldehyde) were recorded.Each isomer of C15 aldehyde showed its own triplet Raman spectrum, while all the isomers of C17 aldehyde showed an identical triplet spectrum.The results were compared with those of isomeric retinal (C20 aldehyde) and retinylideneacetaldehyde (C22 aldehyde) obtained previously.Triplet-sensitized isomerization as well as direct photoisomerization of the all-trans isomer and the complete set of mono-cis isomers of C15, C17, C20, and C22 aldehydes were analyzed by HPLC.Mutual isomerization among the all-trans was seen for C17, C20, and C22 aldehydes.The quantum yield of triplet-sensitized isomerization for each isomer of the above aldehydes was determined. all the results are discussed in terms of triplet potentials with minima at cis and trans positions, the relative stability being dependent on the length of the polyene chain; the cis minima are as stable as the trans minimum for C15 aldehyde, while the cis minima are far less stable than the trans minimum for C17, C20, and C22 aldehydes.

Synthesis of 8-, 9-, 12-, and 13-mono-13C-retinal

The 8-, 9-, 12-, and 13-mono-13C-retinals were synthesized with >98percent chemical purity and 93percent 13C incorporation from 13C-labelled acetonitrile.Their 13C-13C and 13C-1H nmr coupling constants were determined.

Synthesis of 10-, 11-, 19- and 20-mono-13C-retinal

The 10-, 11-, 19- and 20-mono-13C-all-trans-retinals were synthesized with >98percent chemical purity and 92percent 13C incorporation from 13C-labelled acetonitrile and 13C-labelled methyl iodide.Their 13C-13C and 13C-1H NMR coupling constants were measur