5299-98-9

Basic information

• Product Name: (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)penta-2,4-dienenitrile
• Synonyms: (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)penta-2,4-dienenitrile;(7E,9E)-β-Ionylideneacetonitrile;3-Methyl-5-(2,6,6-triMethyl-2-cyclohexen-1-yl)-2,4-pentadienenitrile
• CAS NO: 5299-98-9
• Molecular Formula: C₁₅H₂₁N
• Molecular Weight: 215.33394
• Product Categories: Retinoids;Intermediates
• Mol File: 5299-98-9.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Solubility: Acetone, Chloroform, Dichloromethane, Ether, Ethyl Acetate
• CAS DataBase Reference: (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)penta-2,4-dienenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)penta-2,4-dienenitrile(5299-98-9)
• EPA Substance Registry System: (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)penta-2,4-dienenitrile(5299-98-9)

Safety Data

• Hazardous Substances Data: 5299-98-9(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

β-Ionylideneacetonitrile (cas# 5299-98-9) is a compound useful in organic synthesis.

Upstream product

• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 79-77-6 (E)-β-ionone 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 82648-70-2 diethyl (3-cyano-2-methyl-2-trans-propenyl)phosphonate 
• 94326-16-6 (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile 
• 75-05-8 acetonitrile 
• 23040-22-4 (diphenylphosphoryl)acetonitrile 
• 21658-95-7 diisopropyl (cyanomethyl)phosphonate 
• 53282-28-3 [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride 
• 94326-16-6 3-Hydroxy-3-methyl-1-(2.6.6-trimethyl-cyclohexen-(1)-yl)-penten-(1)-saeure-(5)-nitril, β-Ionolacetonitril 
• 1856-65-1 (4E)-2-cyano-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoic acid 
• 92728-58-0 (4E)-3-methylene-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile 
• 372-09-8 cyanoacetic acid 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 

Downstream Products

• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 142779-20-2 2-Amino-6-methyl-4,6-bis-[(E)-2-(2,6,6-trimethyl-cyclohex-1-enyl)-vinyl]-cyclohexa-1,3-dienecarbonitrile 
• 330808-35-0 3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile 
• 187392-26-3 2,3-dimethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile 
• 6980-79-6 (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal 
• 59955-09-8 (Β-Ionyliden-aethyliden)-acetonitril 
• 129165-44-2 (2E,4E,6E,8E)-7-methyl-9-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-nona-2,4,6,8-tetraenenitrile 
• 6985-27-9 β-apo-14'-carotenal 
• 1856-64-0 2-Cyan-Vitamin-A-saeure 
• 20638-88-4 9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile 
• 1856-68-4 Retinyliden-malonsaeure-mononitril 
• 3917-39-3 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol 
• 74311-19-6 (13Z)-13-Desmethylretinal 
• 29706-62-5 11-cis-13-Demethylretinal 

Relevant articles and documents

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.

Azetidinone-retinoid hybrids: Synthesis and differentiative effects

As a part of a systematic investigation on the synthesis and biological activities of new β-lactam compounds, we examined β-lactam candidates 1, 2E and 2Z and their ability to induce cell proliferation or differentiation. Azetidinone 1 was chosen for its

New syntheses of retinal and its acyclic analog γ-retinal by an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation. A formal route to lycopene and β-carotene

Since the C15 β-end-group aldehyde 10 ((β-ionylidene) acetaldehyde), an excellent intermediate in the syntheses of retinoids, can be synthesized in many ways from β-ionone, and since the corresponding acyclic C15 ψ-end-group aldehyde 5 can easily be synthesized from citral (1) (Scheme 3), we applied the C15 + C5 route to the syntheses of γ-retinal ((all-E)-8) (Scheme 3) and retinal ((all-E)-13) (Scheme 4), and therefore, by coupling (2 x C20 → C 40), to the preparation of lycopene (14) and β-carotene (15) (Scheme 5). Our new syntheses of retinal ((all-E)-13) and γ-retinal ((all-E)-8 use an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation.