CAS 81444-57-7

13-cis-5,6-Epoxy-5,6-dihydroretinoic acid

Description:

13-cis-5,6-Epoxy-5,6-dihydroretinoic acid, with the CAS number 81444-57-7, is a derivative of retinoic acid, which is a metabolite of vitamin A. This compound is characterized by its unique structural features, including a cis configuration at the 13 position and an epoxy group at the 5,6 positions, which contribute to its biological activity. It is known to play a role in various physiological processes, particularly in the regulation of gene expression and cellular differentiation. The compound exhibits potential therapeutic applications, particularly in dermatology and oncology, due to its ability to modulate cell growth and differentiation. Its solubility properties are influenced by its polar functional groups, and it is typically studied in the context of its interactions with nuclear receptors, such as retinoic acid receptors (RARs). As with many retinoids, it may also exhibit side effects, necessitating careful consideration in therapeutic contexts. Overall, 13-cis-5,6-Epoxy-5,6-dihydroretinoic acid is an important compound in the study of retinoid biology and its applications in medicine.

Formula: C₂₀H₂₈O₃

InChI: InChI=1/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14-

InChI key: InChIKey=KEEHJLBAOLGBJZ-NJZIYGCENA-N

SMILES: C(=C/C(=C/C=C/C(=C\C(O)=O)/C)/C)\C12C(C)(O1)CCCC2(C)C

5,6-epoxy-13-cis Retinoic Acid

CAS: 81444-57-7

5,6-epoxy-13-cis Retinoic Acid is a metabolite of 13-cis retinoic acid.

Formula: C₂₀H₂₈O₃

Color and Shape: Solid

Molecular weight: 316.441

Ref: TM-T37916

Isotretinoin EP Impurity G (5,6-Epoxy-13-cis-Retinoic Acid)

CAS: 81444-57-7

Formula: C₂₀H₂₈O₃

Color and Shape: Yellow Solid

Molecular weight: 316.44

Ref: 4Z-T-114010

5,6-Epoxy-13-cis Retinoic Acid

Controlled Product

CAS: 81444-57-7

Applications A metabolite of 13-cis-Retinoic Acid (R250000).
References Samokyszyn, V., et al.: J. Biol. Chem., 262, 14119 (1987), Oldfield, N., et al.: Drug Metabol. Dispos., 18, 1105 (1990), Samokyszyn, V., et al.: Chem. Res. Toxicol., 10, 795 (1997),

Formula: C₂₀H₂₈O₃

Color and Shape: Neat

Molecular weight: 316.43

Ref: TR-E589815

5,6-Epoxy-13-cis retinoic acid

CAS: 81444-57-7

5,6-Epoxy-13-cis retinoic acid (5,6-ER) is the most active metabolite of all-trans-retinoic acid. 5,6-ER binds to the nuclear receptor and acts as a transcription factor. It has been shown to inhibit the growth of several cancer cell lines in vitro, including T47D cells. 5,6-ER also has antacid properties and can be used for the treatment of inflammatory bowel disease. 5,6-ER is found in low concentrations in plasma and tissues and accumulates in high concentrations in rat liver microsomes. The major metabolic pathway includes hydrolysis by trifluoroacetic acid which produces 5,6 epoxyretinoyl coenzyme A (5,6 epoxyretinoyl CoA). This compound is then converted to 5,6 epoxyretinol by an unknown mechanism.

Formula: C₂₀H₂₈O₃

Purity: Min. 95%

Molecular weight: 316.43 g/mol

Ref: 3D-FE22755

Isotretinoin EP Impurity G

CAS: 81444-57-7

Formula: C₂₀H₂₈O₃

Molecular weight: 316.44

Ref: ST-EA-CP-I25006