3-Dehydroretinal

Base Information

• Chemical Name: 3-Dehydroretinal
• CAS No.: 472-87-7
• Molecular Formula: C20H26O
• Molecular Weight: 282.426
• European Community (EC) Number: 207-457-7
• UNII: HV8T003XO1
• DSSTox Substance ID: DTXSID30878517
• Metabolomics Workbench ID: 29029
• Nikkaji Number: J12.671C
• Wikidata: Q5252392
• Wikipedia: Dehydroretinal
• Mol file: 472-87-7.mol

Synonyms:3,4-didehydroretinal;3-dehydroretinal;dehydroretinal

Chemical Property of 3-Dehydroretinal

Chemical Property:

• Vapor Pressure: 1.84E-07mmHg at 25°C
• Boiling Point: 425.9°Cat760mmHg
• Flash Point: 212.5°C
• PSA: 17.07000
• Density: 0.963g/cm³
• LogP: 5.49290
• Storage Temp.: -86?C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 282.198365449
• Heavy Atom Count: 21
• Complexity: 561

Purity/Quality:

99% ^*data from raw suppliers

3-DehydroRetinal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC=C1)(C)C)C=CC(=CC=CC(=CC=O)C)C
• Isomeric SMILES: CC1=C(C(CC=C1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
• Uses: An oxidized derivative of the visual pigment carotenoid.

Technology Process of 3-Dehydroretinal

There total 13 articles about 3-Dehydroretinal 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: 68.0%

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenenitrile (6248-59-5) → 3,4-didehydroretinal (472-87-7)

Guidance literature:

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenenitrile; With diisobutylaluminium hydride; In hexane; at -78 ℃; for 1.5h;

With water; silica gel; In hexane; for 0.5h; Further stages.;

DOI:10.1248/cpb.56.112

Reference yield:

vitamin A2 (79-80-1) → 3,4-didehydroretinal (472-87-7)

Guidance literature:

With manganese(IV) oxide; Petroleum ether;

Reference yield:

1-[(trifluoromethanesulfonyl)oxy]-2,6,6-trimethylcyclohexa-1,3-diene (817203-14-8) → 3,4-didehydroretinal (472-87-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / AsPh₃ / Pd₂(dba)3 / 1-methyl-pyrrolidin-2-one / 4 h / 70 °C

2: 99 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C

3: 135 mg / MnO₂; Na₂CO₃ / CH₂Cl₂ / 1.5 h / 25 °C

With manganese(IV) oxide; triphenyl-arsane; diisobutylaluminium hydride; sodium carbonate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; dichloromethane; 1: Stille cross-coupling;

DOI:10.1039/b411585f

upstream raw materials:

vitamin A₂

1-[(trifluoromethanesulfonyl)oxy]-2,6,6-trimethylcyclohexa-1,3-diene

ethyl 3,4-didehydroretinoate

(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid

Downstream raw materials:

vitamin A₂

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenenitrile

(11Z)-retinal

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.