4-Methoxy Retinoic Acid

Base Information

• Chemical Name: 4-Methoxy Retinoic Acid
• CAS No.: 81121-20-2
• Molecular Formula: C21H30O3
• Molecular Weight: 330.467
• Mol file: 81121-20-2.mol

Synonyms:4-Methoxy Retinoic Acid

Chemical Property of 4-Methoxy Retinoic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 163-165°C
• Boiling Point: 488.78°C at 760 mmHg
• PKA: 4.73±0.33(Predicted)
• Flash Point: 164.859°C
• PSA: 46.53000
• Density: 1.025g/cm³
• LogP: 5.22750
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxy retinoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An impurity contained in samples of all trans-retinoic acid.

Technology Process of 4-Methoxy Retinoic Acid

There total 5 articles about 4-Methoxy 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:

methanol (67-56-1) + vitamin A Propionate (7069-42-3) → all-trans-retinoic-acid (302-79-4) + 4-methoxyretinoic acid (81121-20-2)

Guidance literature:

With potassium hydroxide; silver(l) oxide;

DOI:10.1016/j.bmcl.2005.05.050

Reference yield:

(13E)-3,7-dimethyl-9-[(3RS)-3-methoxy-2,6,6-trimethylcyclohexenyl]-2,4,6,8-nontetraenoate methyl ester (163808-81-9) → 4-methoxyretinoic acid (81121-20-2)

Guidance literature:

With potassium hydroxide; In methanol; water; at 65 ℃; for 4h;

Reference yield:

all-trans-retinoic-acid (302-79-4) → 4-methoxyretinoic acid (81121-20-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium methylate / methanol / 4 h / 55 °C / Inert atmosphere

2.1: manganese(IV) oxide / dichloromethane / 24 h / 28 °C

3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 10 - 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 10 - 20 °C

4.2: 2 h / 10 - 20 °C

5.1: potassium hydroxide / methanol; water / 4 h / 65 °C

With manganese(IV) oxide; sodium tetrahydroborate; sodium methylate; sodium hydride; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

methanol

vitamin A Propionate

all-trans-retinoic-acid

all-trans-methyl retinoate

Refernces

• 1、 Allegrone, Gianna,Brenna, Elisabetta,Fronza, Giovanni,Fuganti, Claudio,Giovenzana, Tommaso,Malpezzi, Luciana,Barlocchi, Enrico,Pellegatta, Cesare. "Impurity analysis of retinoic acid samples". . p. 3528 - 3531. Retrieved 2007/10/03.