(E,E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoic acid

Base Information

• Chemical Name: (E,E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoic acid
• CAS No.: 14398-42-6
• Molecular Formula: C15H22 O2
• Molecular Weight: 234.338
• NSC Number: 23978
• Nikkaji Number: J362.518D
• Mol file: 14398-42-6.mol

Synonyms:C15 acid;(E,E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoic acid;14398-42-6;trans-beta-Ionylidene acetic acid;BASF 36592;(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dienoic acid;RO 4-6230;2,4-Pentadienoic acid, 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E,E)-;all-trans-5-(2,6,6-Trimethylcyclohexen-1-yl)-3-methylpenta-2,4-diene-1 acid;SCHEMBL8776466;SCHEMBL11790962;NSC23978;NSC-23978;trans,trans-beta-Ionylideneacetic acid;(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadienoic acid;(2e,4e)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl) penta-2,4-dienoic acid;4941-93-9

Chemical Property of (E,E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoic acid

Chemical Property:

• Vapor Pressure: 1.06E-06mmHg at 25°C
• Boiling Point: 376.3°Cat760mmHg
• Flash Point: 275.8°C
• Density: 1.029g/cm³
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 395

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC(=O)O)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C(=O)O)/C

Technology Process of (E,E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoic acid

There total 25 articles about (E,E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

ethyl β-ionylidene acetate (37384-77-3) → (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid (14398-42-6)

Guidance literature:

ethyl β-ionylidene acetate; With water; sodium hydroxide; In methanol; for 2h; Reflux; Inert atmosphere;

With acetic acid; citric acid; at 0 ℃; pH=6; Inert atmosphere;

DOI:10.1016/j.ejmech.2009.03.029

Reference yield: 37.0%

(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienoic acid methyl ester (5300-00-5) → (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid (14398-42-6)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; for 12h; Ambient temperature;

DOI:10.1021/jm9801354

Reference yield: 34.0%

(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate (17974-55-9) → (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid (14398-42-6)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 20 ℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique;

DOI:10.1021/acs.orglett.0c02064

upstream raw materials:

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

(2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal

(2Z,4E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-2,4-pentadienoic acid

(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate

Downstream raw materials:

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol

3-methyl-5-(2,2,6-trimethyl-cyclohexyl)-valeric acid

3-methyl-5t-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2t,4-dienoyl chloride

methyl trans-3'-keto-β-ionylideneacetate

Refernces

• 1、 Sadikoglou, Eldem,Magoulas, George,Theodoropoulou, Christina,Athanassopoulos, Constantinos M.,Giannopoulou, Efstathia,Theodorakopoulou, Olga,Drainas, Denis,Papaioannou, Dionysios,Papadimitriou, Evangelia. "Effect of conjugates of all-trans-retinoic acid and shorter polyene chain analogues with amino acids on prostate cancer cell growth". experimental part. p. 3175 - 3187. Retrieved 2009/12/04.
• 2、 Jones, Paul,Villeneuve, Gérald B.,Fei, Chengpei,DeMarte, Josie,Haggarty, Allison J.,Nwe, Khin Than,Martin, Deborah A.,Lebuis, Anne-Marie,Finkelstein, Joshua M.,Gour-Salin, Barbara J.,Chan, Tak Hang,Leyland-Jones, Brian R.. "Synthesis and structure-activity relationships of 2- pyrazinylcarboxamidobenzoates and β-ionylideneacetamidobenzoates with retinoidal activity". . p. 3062 - 3077. Retrieved 2007/10/03.