N-(2-Hydroxyethyl)retinamide

Base Information

• Chemical Name: N-(2-Hydroxyethyl)retinamide
• CAS No.: 33631-47-9
• Molecular Formula: C₂₂H₃₃NO₂
• Molecular Weight: 343.51
• UNII: ZBJ8HC23XW
• DSSTox Substance ID: DTXSID801309774
• Nikkaji Number: J394.885D
• Pharos Ligand ID: YQUMGD7ZM1AX
• ChEMBL ID: CHEMBL60405
• Mol file: 33631-47-9.mol

Synonyms:N-(2-hydroxyethyl)retinamide;N-(2-hydroxyethyl)retinamide, (13-cis)-isomer

Chemical Property of N-(2-Hydroxyethyl)retinamide

Chemical Property:

• Vapor Pressure: 2.39E-14mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 549.1°Cat760mmHg
• Flash Point: 285.9°C
• PSA: 52.82000
• Density: 1.013g/cm³
• LogP: 5.46680
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 343.251129295
• Heavy Atom Count: 25
• Complexity: 616

Purity/Quality:

99% ^*data from raw suppliers

N-(2-HYDROXYETHYL)RETINAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NCCO)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)NCCO)/C)/C

Technology Process of N-(2-Hydroxyethyl)retinamide

There total 5 articles about N-(2-Hydroxyethyl)retinamide 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) → (2E,4E,6E,8E)-N-(2-hydroxyethyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide (33631-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile; tetrahydrofuran / 0.33 h / -18 °C

2: acetonitrile; tetrahydrofuran; methanol / 2.33 h / -18 - 20 °C

With triethylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1023/A:1015388429085

Reference yield:

all-trans-retinoic-acid (302-79-4) + ethanolamine (141-43-5) → (2E,4E,6E,8E)-N-(2-hydroxyethyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide (33631-47-9)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jm200256g

Reference yield:

retinoyl chloride (53839-60-4) + ethanolamine (141-43-5) → (2E,4E,6E,8E)-N-(2-hydroxyethyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide (33631-47-9)

Guidance literature:

In benzene; at 10 - 15 ℃; for 0.75h;

DOI:10.1002/jps.2600730610

upstream raw materials:

retinoyl chloride

ethanolamine

all-trans-retinoic-acid

Refernces

• 1、 Campos-Sandoval, José Angel,Redondo, Clara,Kinsella, Gemma K.,Pal, Akos,Jones, Geraint,Eyre, Gwen S.,Hirst, Simon C.,Findlay, John B. C.. "Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor". experimental part. p. 4378 - 4387. Retrieved 2011/09/14.