(±)-4-(1H-imidazol-1-yl)-methyl retinoate

Base Information

• Chemical Name: (±)-4-(1H-imidazol-1-yl)-methyl retinoate
• CAS No.: 303731-00-2
• Molecular Formula: C₂₄H₃₂N₂O₂
• Molecular Weight: 380.53
• Mol file: 303731-00-2.mol

Synonyms:(±)-4-(1H-imidazol-1-yl)-methyl retinoate

Chemical Property of (±)-4-(1H-imidazol-1-yl)-methyl retinoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (±)-4-(1H-imidazol-1-yl)-methyl retinoate

There total 4 articles about (±)-4-(1H-imidazol-1-yl)-methyl retinoate 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: 95.0%

4-Hydroxyretinoic acid methyl ester (38030-59-0) + 1,1'-carbonyldiimidazole (530-62-1) → (±)-4-(1H-imidazol-1-yl)-methyl retinoate (303731-00-2)

Guidance literature:

In acetonitrile; at 20 ℃;

DOI:10.1016/S0960-894X(00)00391-7

Reference yield:

all-trans-methyl retinoate (339-16-2) → (±)-4-(1H-imidazol-1-yl)-methyl retinoate (303731-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / MnO₂ / CH₂Cl₂ / 24 h / 20 °C

2: 85 percent / NaBH₄ / methanol / 0.5 h / 20 °C

3: 89.5 percent / acetonitrile / 0.5 h / 20 °C

With manganese(IV) oxide; sodium tetrahydroborate; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm0401457

Reference yield:

all-trans-retinoic-acid (302-79-4) → (±)-4-(1H-imidazol-1-yl)-methyl retinoate (303731-00-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / methanol; benzene; hexane / 0.75 h / 20 °C

2: 61 percent / MnO₂ / CH₂Cl₂ / 24 h / 20 °C

3: 85 percent / NaBH₄ / methanol / 0.5 h / 20 °C

4: 89.5 percent / acetonitrile / 0.5 h / 20 °C

With manganese(IV) oxide; sodium tetrahydroborate; In methanol; hexane; dichloromethane; acetonitrile; benzene;

DOI:10.1021/jm0401457

upstream raw materials:

4-Hydroxyretinoic acid methyl ester

1,1'-carbonyldiimidazole

all-trans-retinoic-acid

all-trans-methyl retinoate

Downstream raw materials:

4-(1H-imidazole-1-yl)retinoic acid

Refernces

• 1、 Njar, Vincent C.O.,Nnane, Ivo P.,Brodie, Angela M.H.. "Potent inhibition of retinoic acid metabolism enzyme(s) by novel azolyl retinoids". . p. 1905 - 1908. Retrieved 2007/10/03.