14393-45-4

Basic information

• Product Name: 2-Propenoic acid, 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E)-
• CAS NO: 14393-45-4
• Molecular Formula: C12H18O2
• Molecular Weight: 194.274
• Mol File: 14393-45-4.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E)-(14393-45-4)
• EPA Substance Registry System: 2-Propenoic acid, 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E)-(14393-45-4)

Safety Data

• Hazardous Substances Data: 14393-45-4(Hazardous Substances Data)

Upstream product

• 80922-54-9 (E)-3-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-propensaeure-ethylester 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 126456-65-3 ethyl 3-(2,6,6-trimethyl-2-cyclohexenyl)-2-propenoate 
• 105-36-2 ethyl bromoacetate 
• 79636-77-4 β-ionone 
• 79-77-6 (E)-β-ionone 

Downstream Products

• 14393-44-3 (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)prop-2-en-1-ol 
• 472-66-2 (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde 
• 53291-85-3 Acetic acid (E)-3-(2,6,6-trimethyl-cyclohex-1-enyl)-allyl ester 
• 53018-97-6 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal 
• 129165-49-7 7E (9-²H₂)3-(2,6,6-trimethyl-1-cyclohexenyl)propen-1-ol 
• 14393-46-5 methyl (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylate 
• 69258-08-8 (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride 
• 1259012-84-4 (E)-N-methyl-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylamide 
• 52209-30-0 (E)-N,N-dimethyl-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylamide 
• 40244-46-0 (Z)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylic acid 
• 53291-87-5 methyl (Z)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylate 

Relevant articles and documents

Ligand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin

Inherited blinding diseases retinitis pigmentosa (RP) and a subset of Leber's congenital amaurosis (LCA) are caused by the misfolding and mistrafficking of rhodopsin molecules, which aggregate and accumulate in the endoplasmic reticulum (ER), leading to photoreceptor cell death. One potential therapeutic strategy to prevent the loss of photoreceptors in these conditions is to identify opsin-binding compounds that act as chemical chaperones for opsin, aiding its proper folding and trafficking to the outer cell membrane. Aiming to identify novel compounds with such effect, a rational ligand-based approach was applied to the structure of the visual pigment chromophore, 11-cis-retinal, and its locked analogue 11-cis-6mr-retinal. Following molecular docking studies on the main chromophore binding site of rhodopsin, 49 novel compounds were synthesized according to optimized one-to seven-step synthetic routes. These agents were evaluated for their ability to compete for the chromophore binding site of opsin, and their capacity to increase the trafficking of the P23H opsin mutant from the ER to the cell membrane. Different new molecules displayed an effect in at least one assay, acting either as chemical chaperones or as stabilizers of the 9-cis-retinal-rhodopsin complex. These compounds could provide the basis to develop novel therapeutics for RP and LCA.

Synthesis of short retinoidal amides related to fenretinide: antioxidant activities and differentiation-inducing ability

Purpose: By a scaffold shortening strategy, a small series of retinoidal amides fenretinide (4-HPR) analogs have been synthesized from α, β-ionones and tested for their antiproliferative and differentiating activities, and antioxidant effect. Methods: The

OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE

Compounds and compositions of said compounds along with methods of use of compounds are disclosed for treating ophthalmic conditions related to mislocalization of opsin proteins, the misfolding of mutant opsin proteins and the production of toxic visual cycle products that accumulate in the eye. Compounds and compositions useful in the these methods, either alone or in combination with other therapeutic agents, are also described.