(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

Base Information

• Chemical Name: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
• CAS No.: 33532-44-4
• Molecular Formula: C20H26 O2
• Molecular Weight: 298.425
• Wikidata: Q76727521
• Metabolomics Workbench ID: 42106
• Mol file: 33532-44-4.mol

Synonyms:4OVA;4-Oxo-all-trans-retinal;3,7-Dimethyl-9-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-all-trans-2,4,6,8-nonatetraenal;(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

Chemical Property of (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

Chemical Property:

• Vapor Pressure: 6.98E-09mmHg at 25°C
• Melting Point: 107-107°C
• Boiling Point: 466.6°Cat760mmHg
• Flash Point: 173.5°C
• PSA: 34.14000
• Density: 1.007g/cm³
• LogP: 4.89590
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 298.193280068
• Heavy Atom Count: 22
• Complexity: 593

Purity/Quality:

97% ^*data from raw suppliers

4-KetoRetinal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=O)CC1)(C)C)C=CC(=CC=CC(=CC=O)C)C
• Isomeric SMILES: CC1=C(C(C(=O)CC1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
• Uses: An inactive catabolite of Retinoic acid.

Technology Process of (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

There total 28 articles about (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal 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: 84.0%

4-hydroxy-all-trans-retinal (18344-42-8) → 4-ketoretinal (33532-44-4,71423-69-3)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/ja00177a044

Reference yield: 80.0%

4-hydroxy-all-trans-retinal (18344-42-8) → 4-keto-all-trans-retinal (33532-44-4)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; for 1.5h; Ambient temperature;

Reference yield: 80.0%

all-trans-Retinal (116-31-4) → 4-keto-all-trans-retinal (33532-44-4)

Guidance literature:

With N-Bromosuccinimide; N,N-diethylaniline; In dichloromethane; water; acetonitrile; at -15 ℃; for 0.166667h;

DOI:10.1039/c9dt02189b

upstream raw materials:

RETINOL

all-trans-Retinal

(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenal

2-(4'-oxoretinylidene)-dimedone

Downstream raw materials:

nitrile of all-trans-4-ketoretinoic acid

all-trans-4-oxoretinol

4-keto-13-cis-retinal

4-Oxo-retinoic acid methyl ester

Refernces

• 1、 Dominguez, Marta,Alvarez, Rosana,Martras, Silvia,Farres, Jaume,Pares, Xavier,De Lera, Angel R.. "Synthesis of ring-oxidized retinoids as substrates of mouse class I alcohol dehydrogenase (ADH1)". . p. 3368 - 3373. Retrieved 2007/10/03.
• 2、 Hashimoto, Masaru,Fujimoto, Yukari. "One step and convenient preparations of 4-hydroxyretinal and 4- oxoretinal". . p. 3793 - 3797. Retrieved 2007/10/03.