150737-18-1

Basic information

• Product Name: 4-Keto 9-cis Retinoic Acid
• Synonyms: (2E,4E,6Z,8E)-4-Keto-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic Acid;4-Keto 9-cis Retinoic Acid;4-Keto-9-cis-tretinoin;4-Oxo-9-cis-Retinoic Aci;4-Oxo-9-cis-Retinoic Acid
• CAS NO: 150737-18-1
• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.42
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Retinoids;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Retinoids
• Mol File: 150737-18-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 172-1740C
• Boiling Point: 509.922°C at 760 mmHg
• Flash Point: 276.279°C
• Appearance: /
• Density: 1.071g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• PKA: 4.73±0.33(Predicted)
• Stability: Light and Temperature Sensitive
• CAS DataBase Reference: 4-Keto 9-cis Retinoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Keto 9-cis Retinoic Acid(150737-18-1)
• EPA Substance Registry System: 4-Keto 9-cis Retinoic Acid(150737-18-1)

Safety Data

• Hazardous Substances Data: 150737-18-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

A metabolite of Retinoic acid

InChI:InChI=1/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7-,15-13+

Upstream product

• 40834-42-2 5-hydroxy-4-methyl-5H-furan-2-one 
• 63184-93-0 (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide 
• 71748-57-7 (2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 
• 4759-48-2 13-cis-retinoic acid 
• 75281-25-3 4-Hydroxy-13-cis-Retinoic acid 
• 38030-57-8 (6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid 
• 68-26-8 RETINOL 
• 116-31-4 all-trans-Retinal 
• 302-79-4 all-trans-retinoic-acid 
• 66592-72-1 4-hydroxyretinoic acid 
• 1425830-47-2 C₂₀H₂₈O₃ 
• 1425830-36-9 C₂₀H₂₈O₃ 
• 81121-19-9 (2E,4E,6E,8E)-9-(3-Acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 38030-59-0 4-Hydroxyretinoic acid methyl ester 

Downstream Products

• 38030-57-8 13-cis-4-Oxoretinoic acid 
• 75281-25-3 4-Hydroxy-13-cis-Retinoic acid 
• 81121-27-9 rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid 
• 66592-72-1 4-hydroxyretinoic acid 

Relevant articles and documents

AN IMPROVED PROCESS FOR THE PREPARATION OF 4-OXOISOTRETINOIN

The present invention relates to an improved process for the preparation of 4-Oxoisotretinoin and purification process of 4-Oxoisotretinoin (I) and crystalline 5 form of 4-Oxoisotretinoin (I).

Stereoselective formation and metabolism of 4-hydroxy-retinoic acid enantiomers by cytochrome p450 enzymes

All-trans-retinoic acid (atRA), the major active metabolite of vitamin A, plays a role in many biological processes, including maintenance of epithelia, immunity, and fertility and regulation of apoptosis and cell differentiation. atRA is metabolized mainly by CYP26A1, but other P450 enzymes such as CYP2C8 and CYP3As also contribute to atRA 4-hydroxylation. Although the primary metabolite of atRA, 4-OH-RA, possesses a chiral center, the stereochemical course of atRA 4-hydroxylation has not been studied previously. (4S)- and (4R)-OH-RA enantiomers were synthesized and separated by chiral column HPLC. CYP26A1 was found to form predominantly (4S)-OH-RA. This stereoselectivity was rationalized via docking of atRA in the active site of a CYP26A1 homology model. The docked structure showed a well defined niche for atRA within the active site and a specific orientation of the β-ionone ring above the plane of the heme consistent with stereoselective abstraction of the hydrogen atom from the pro-(S)-position. In contrast to CYP26A1, CYP3A4 formed the 4-OH-RA enantiomers in a 1:1 ratio and CYP3A5 preferentially formed (4R)-OH-RA. Interestingly, CYP3A7 and CYP2C8 preferentially formed (4S)-OH-RA from atRA. Both (4S)- and (4R)-OH-RA were substrates of CYP26A1 but (4S)-OH-RA was cleared 3-fold faster than (4R)-OH-RA. In addition, 4-oxo-RA was formed from (4R)-OH-RA but not from (4S)-OH-RA by CYP26A1. Overall, these findings show that (4S)-OH-RA is preferred(4R)-OH-RA by the enzymes regulating atRA homeostasis. The stereoselectivity observed in CYP26A1 function will aid in better understanding of the active site features of the enzyme and the disposition of biologically active retinoids.

All-Trans-Retinol: All-Trans-13,14-Dihydroretinol Saturase and Methods of Its Use

Compositions of all-trans-retinol: all-trans-13,14-dihydroretinal saturase and methods of use thereof are provided.