4-Oxoretinol

Base Information

• Chemical Name: 4-Oxoretinol
• CAS No.: 62702-55-0
• Molecular Formula: C20H28O2
• Molecular Weight: 300.441
• UNII: 6FFM6M3NPT
• DSSTox Substance ID: DTXSID80866949
• Nikkaji Number: J648.935D
• Wikidata: Q27093646
• Metabolomics Workbench ID: 42002
• Mol file: 62702-55-0.mol

Synonyms:4-ketoretinol;4-oxoretinol

Chemical Property of 4-Oxoretinol

Chemical Property:

• Vapor Pressure: 1.27E-10mmHg at 25°C
• Melting Point: 102-106oC
• Boiling Point: 465.5°Cat760mmHg
• PKA: 14.09±0.10(Predicted)
• Flash Point: 198°C
• PSA: 37.30000
• Density: 1.013g/cm³
• LogP: 4.68930
• Storage Temp.: Amber Vial, -20?C Freezer
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 300.208930132
• Heavy Atom Count: 22
• Complexity: 567

Purity/Quality:

98%Min ^*data from raw suppliers

4-KetoRetinol(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1=O)(C)C)C=CC(=CC=CC(=CCO)C)C
• Isomeric SMILES: CC1=C(C(CCC1=O)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C
• Uses: 4-KETORETINOL activate gene expression through binding to nuclear receptor proteins. They are useful for treating leukemia, lymphoma, squamous cell carcinoma, deep (cystic) acne, psoriasis, and photodamaged or aging skin. A metabolite of Retinol.

Technology Process of 4-Oxoretinol

There total 9 articles about 4-Oxoretinol 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: 90.0%

4-ketoretinal (33532-44-4,71423-69-3) → 4-ketoretinol (62702-55-0)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 1h;

DOI:10.1021/ja00177a044

Reference yield: 90.0%

4-keto-all-trans-retinal (33532-44-4) → all-trans-4-oxoretinol (62702-55-0)

Guidance literature:

With lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride;

Reference yield:

RETINOL (68-26-8) → 5,6-Epoxyretinol (512-39-0) + vitamin A2 (79-80-1) + all-trans-4-oxoretinol (62702-55-0) + 5,8-Epoxyretinol

Guidance literature:

With dihydrogen peroxide; iron(III) tetraphenylporphyrin; In methanol; dichloromethane; at 30 ℃; for 24h; Yield given. Further byproducts given. Yields of byproduct given;

upstream raw materials:

Retinol acetate

4-keto-all-trans-retinal

RETINOL

all-trans-Retinal

Downstream raw materials:

3-formyl-4-ketoretinyl tert-butyldimethylsilyl ether

6-diazo-3-[(1E,3E,5E,7Z)-8-formyl-3,7-dimethylnona-1,3,5,7-tetraenyl]-2,4,4-trimethylcyclohex-2-en-1-one

3-formyl-4-ketoretinol

4-ketoretinyl tert-butyldimethylsilyl ether

Refernces

• 1、 Boehm, Marcus F.,Gawinowicz, Mary Ann,Foucault, Alain,Derguini, Fadila,Nakanishi, Koji. "Photoaffinity labeling studies of bacteriorhodopsin with [ 15-3H]-3-diazo-4-keto-all-trans-retinal". . p. 7779 - 7782. Retrieved 2007/10/02.