rac 4-Hydroxy-9-cis-retinoic Acid

Base Information

• Chemical Name: rac 4-Hydroxy-9-cis-retinoic Acid
• CAS No.: 150737-17-0
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.441
• Mol file: 150737-17-0.mol

Synonyms:rac 4-Hydroxy-9-cis-retinoic Acid

Chemical Property of rac 4-Hydroxy-9-cis-retinoic Acid

Chemical Property:

• Vapor Pressure: 2.22E-12mmHg at 25°C
• Melting Point: 130-133°C
• Boiling Point: 506.5°C at 760 mmHg
• Flash Point: 274.2°C
• Density: 1.075g/cm³
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

rac4-Hydroxy-9-cis-retinoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A metabolite of 9-cis-Retinoic acid (R245000).

Technology Process of rac 4-Hydroxy-9-cis-retinoic Acid

There total 10 articles about rac 4-Hydroxy-9-cis-retinoic Acid 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:

all-trans-retinoic-acid (302-79-4) → 4-ketoretinoic acid (38030-57-8,71748-58-8,100897-08-3,112924-95-5,150737-18-1,150737-19-2) + 4-hydroxyretinoic acid (66592-72-1,73366-04-8,75281-25-3,81176-70-7,150737-17-0)

Guidance literature:

With rat reductase; NADPH; In aq. phosphate buffer; at 37 ℃; Kinetics; Enzymatic reaction;

DOI:10.1124/mol.117.111039

Reference yield:

all-trans-retinoic-acid (302-79-4) → 4-hydroxyretinoic acid (66592-72-1,73366-04-8,75281-25-3,81176-70-7,150737-17-0)

Guidance literature:

With cytochrome P₄₅₀ 3A₄ enzyme; water; NADPH; In aq. phosphate buffer; at 37 ℃; pH=7.4; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1074/jbc.M112.404475

Reference yield:

RETINOL (68-26-8) → 4-ketoretinoic acid (38030-57-8,71748-58-8,100897-08-3,112924-95-5,150737-18-1,150737-19-2) + 4-hydroxyretinoic acid (66592-72-1,73366-04-8,75281-25-3,81176-70-7,150737-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2-amino-2-hydroxymethyl-1,3-propanediol; bovine serum albumin / retinal pigment epithelium (RPE) microsomes / 1 h / 37 °C / pH 8.8 / Enzymatic reaction

1.2: pH 4.0

2.1: N-acetylglucosaminyltransferase I-negative HEK-293S cells transfected with cytochrome P₄₅₀ enzymes CYP₂₆C₁ (HEK-CYP₂₆C₁ cells) / 4 h / Enzymatic reaction

With 2-amino-2-hydroxymethyl-1,3-propanediol; bovine serum albumin; retinal pigment epithelium (RPE) microsomes; N-acetylglucosaminyltransferase I-negative HEK-293S cells transfected with cytochrome P₄₅₀ enzymes CYP₂₆C₁ (HEK-CYP₂₆C₁ cells);

upstream raw materials:

rac-(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid ethyl ester

(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

(2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide

ethyl (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate

Downstream raw materials:

C₂₀H₂₈O₃

C₂₀H₂₈O₃

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

4-ketoretinoic acid

Refernces

• 1、 Zhao, Yan,Wan, Debin,Yang, Jun,Hammock, Bruce D.,De Montellano, Paul R. Ortiz. "Catalytic activities of tumor-specific human cytochrome P450 CYP2W1 toward endogenous substrates". . p. 771 - 780. Retrieved 2017/02/10.
• 2、 Shimshoni, Jakob A.,Roberts, Arthur G.,Scian, Michele,Topletz, Ariel R.,Blankert, Sean A.,Halpert, James R.,Nelson, Wendel L.,Isoherranen, Nina. "Stereoselective formation and metabolism of 4-hydroxy-retinoic acid enantiomers by cytochrome p450 enzymes". . p. 42223 - 42232. Retrieved 2013/02/22.