62702-55-0

Basic information

• Product Name: 4-KETORETINOL
• Synonyms: 9-(2,6,6-TRIMETHYL-3-KETO-1-CYCLOHEXEN-1-YL)-3,7-DIMETHYL-2,4,6,8-NONATETRAEN-1-OL;4-KETORETINOL;9-cis 4-Ketoretinol;9-cis-4-Oxo-retinol;4-oxoretinol;15-Hydroxyretin-4-one;3-(9-Hydroxy-3,7-diMethyl-1,3,5,7-nonatetraenyl)-2,4,4- triMethyl-2-cyclohexen-1-one
• CAS NO: 62702-55-0
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.44
• Product Categories: Retinoids;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 62702-55-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 102-106°C
• Boiling Point: 465.5°Cat760mmHg
• Flash Point: 198°C
• Appearance: /
• Density: 1.013g/cm³
• Vapor Pressure: 1.27E-10mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: Amber Vial, -20?C Freezer
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 14.09±0.10(Predicted)
• Stability: Unstable! Light, Temperature and Moisture Sensitive
• CAS DataBase Reference: 4-KETORETINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-KETORETINOL(62702-55-0)
• EPA Substance Registry System: 4-KETORETINOL(62702-55-0)

Safety Data

• Hazardous Substances Data: 62702-55-0(Hazardous Substances Data)

Usage

Description

4-KETORETINOL, a metabolite of Retinol, is a bioactive compound that plays a crucial role in various biological processes. It possesses the ability to activate gene expression by binding to nuclear receptor proteins, making it a promising candidate for therapeutic applications.

Uses

Used in Oncology:
4-KETORETINOL is used as an anticancer agent for treating various types of cancer, including leukemia, lymphoma, and squamous cell carcinoma. Its gene expression activation properties contribute to the inhibition of tumor growth and progression, offering a potential therapeutic approach for cancer treatment.
Used in Dermatology:
4-KETORETINOL is used as a therapeutic agent for treating skin conditions such as deep (cystic) acne, psoriasis, and photodamaged or aging skin. Its ability to activate gene expression helps in regulating skin cell functions, promoting skin health, and improving the appearance of the skin.
As a Metabolite of Retinol:
4-KETORETINOL, being a metabolite of Retinol, plays a significant role in maintaining overall health and well-being. Its presence in the body contributes to the regulation of various physiological processes, highlighting its importance in maintaining a healthy state.

InChI:InChI=1/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+

Upstream product

• 18344-42-8 4-hydroxy-all-trans-retinal 
• 78508-49-3 (2E,4E,6E,8E)-9-(3-Bromo-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenal 
• 116-31-4 all-trans-Retinal 
• 68-26-8 RETINOL 
• 33532-44-4 4-keto-all-trans-retinal 
• 127-47-9 Retinol acetate 
• 33532-44-4 4-ketoretinal 

Downstream Products

• 129467-12-5 3-formyl-4-ketoretinyl tert-butyldimethylsilyl ether 
• 129467-08-9 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 
• 129467-13-6 3-formyl-4-ketoretinol 
• 129467-11-4 4-ketoretinyl tert-butyldimethylsilyl ether 

Relevant articles and documents

Iron(III)Porphinate/H2O2-Mediated Conversion of All-(E)-Retinol

The reaction of hydrogen peroxide with all-(E)-retinol (1) catalyzed by (meso-tetraphenylporphinato)iron(III) led to the formation of 4-hydroxyretinol (2), 4-oxoretinol (3), 5,8-epoxyretinol (4), 5,6-epoxyretinol (5), 3-dehydroretinol (6), all-(E)- and 12-(Z)-retroretinol (7/7a) as well as all-(E)- and 12-(Z)-anhydroretinol (8/8a) as major non-volatile products.The conversion products were characterized by comparison of their chromatographic (HPLC) and spectroscopic data (UV; MS; 1H and 13C NMR) with those of synthesized reference compounds.The observed product formation supports the hypothesis of a C4 centered radical as the key intermediate of all-(E)-retinol conversion. - Keywords: 5,6- and 5,8-Epoxyretinol, 4-Hydroxyretinol, 4-Oxoretinol, Retinol Conversion