Retinoic acid, 5,6-epoxy-5,6-dihydro-, methyl ester

Base Information

• Chemical Name: Retinoic acid, 5,6-epoxy-5,6-dihydro-, methyl ester
• CAS No.: 7432-30-6
• Molecular Formula: C21H30O3
• Molecular Weight: 330.4611
• DSSTox Substance ID: DTXSID101222832
• Nikkaji Number: J121.831J
• Mol file: 7432-30-6.mol

Synonyms:7432-30-6;5,6-Epoxy-5,6-dihydroretinoic acid methyl ester;Retinoic acid, 5,6-epoxy-5,6-dihydro-, methyl ester;Methyl-5,6-monoepoxyretinoate;FIWDPTZCMLYHJY-FEPFPIPXSA-N;DTXSID101222832;Methyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-2,4,6,8-nonatetraenoate #

Chemical Property of Retinoic acid, 5,6-epoxy-5,6-dihydro-, methyl ester

Chemical Property:

• Vapor Pressure: 3.08E-07mmHg at 25°C
• Boiling Point: 419.3°Cat760mmHg
• Flash Point: 178.2°C
• PSA: 38.83000
• Density: 1.057g/cm³
• LogP: 4.90220
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 330.21949481
• Heavy Atom Count: 24
• Complexity: 621

Purity/Quality:

Methyl5,6-Monoepoxyretinoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC=CC(=CC(=O)OC)C)C=CC12C(CCCC1(O2)C)(C)C
• Isomeric SMILES: C/C(=C\C=C\C(=C\C(=O)OC)\C)/C=C/C12C(CCCC1(O2)C)(C)C
• Uses: Methyl 5,6-Monoepoxyretinoate is an impurity in the synthesis of Ro 22-5112 (R637180), a retinoid that has been used in a QSAR analysis for the use of retinoids as a carcinogenesis inhibitor.

Technology Process of Retinoic acid, 5,6-epoxy-5,6-dihydro-, methyl ester

There total 6 articles about Retinoic acid, 5,6-epoxy-5,6-dihydro-, methyl ester 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: 80.3%

all-trans-methyl retinoate (339-16-2) → Methyl ester of 5,6-epoxy-(E)-retinoic acid (7432-30-6)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; for 1h; ice bath;

DOI:10.1271/bbb.58.140

Reference yield: 72.0%

methanol (67-56-1) + 5,6-epoxy-5,6-dihydroretinal (739-13-9) → Methyl ester of 5,6-epoxy-(E)-retinoic acid (7432-30-6)

Guidance literature:

With sodium cyanide; manganese(IV) oxide; acetic acid; at 4 - 20 ℃;

DOI:10.1023/A:1021245616117

Reference yield:

all-trans-retinoic-acid (302-79-4) → Methyl ester of 5,6-epoxy-(E)-retinoic acid (7432-30-6)

Guidance literature:

Multi-step reaction with 2 steps

2: 80.3 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂; H₂O / 1 h / ice bath

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water;

DOI:10.1271/bbb.58.140

upstream raw materials:

all-trans-methyl retinoate

diazomethane

all-trans-retinoic-acid

all-trans-5,6-Epoxyretinoic acid

Downstream raw materials:

all-trans-5,6-Epoxyretinoic acid

Refernces

• 1、 Mironova,Leont'eva,Shevyakov,Alexeeva,Shvets,Demina,Krasnokutskaya,Finkel'shtein,Khodonov. "A convenient synthesis of retinal derivatives with modified trimethylcyclohexene ring". . p. 487 - 493. Retrieved 2007/10/03.
• 2、 Samokyszyn, Victor M.,Chen, Tao,Maddipati, Krishna Rao,Franz, Thomas J.,Lehman, Paul A.,Lloyd, Roger V.. "Free Radical Oxidation of (E)-Retinoic Acid by Prostaglandin H Synthase". . p. 807 - 815. Retrieved 2007/10/03.