alpha-Retinoic acid

Base Information

• Chemical Name: alpha-Retinoic acid
• CAS No.: 52978-64-0
• Deprecated CAS: 29448-54-2
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• DSSTox Substance ID: DTXSID90858774
• Nikkaji Number: J82.350C
• Mol file: 52978-64-0.mol

Synonyms:alpha-Retinoic acid;4,5-Didehydro-5,6-dihydroretinoic acid;52978-64-0;Retinoic acid, 4,5-didehydro-5,6-dihydro-;alpha-Vitamin A acid;SCHEMBL12494830;SCHEMBL15609523;DTXSID90858774

Chemical Property of alpha-Retinoic acid

Chemical Property:

• PSA: 37.30000
• LogP: 5.45850
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 300.208930132
• Heavy Atom Count: 22
• Complexity: 554

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(C1C=CC(=CC=CC(=CC(=O)O)C)C)(C)C
• Isomeric SMILES: CC1=CCCC(C1/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)(C)C

Technology Process of alpha-Retinoic acid

There total 2 articles about alpha-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:

α-ionone (160096-44-6) + methylmagnesium bromide (75-16-1) + dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate (419550-09-7) → (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-2-enyl)nona-2,4,6,8-tetraenoic acid (58526-49-1) + 4,5-didehydro-5,6-dihydroretinoic acid (52978-64-0)

Guidance literature:

α-ionone; dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate; With n-butyllithium; diisopropylamine; In 1,2-dimethoxyethane; for 1h; Heating;

methylmagnesium bromide; at 0 ℃;

With potassium hydroxide; In ethanol; water; at 40 ℃; for 45h; Further stages.; acidified with cold HCl;

DOI:10.1002/ejoc.200300029

Reference yield:

→ 4,5-didehydro-5,6-dihydroretinoic acid (52978-64-0)

Guidance literature:

Dehydroretinal;

Reference yield:

4,5-didehydro-5,6-dihydroretinoic acid (52978-64-0) + acetyl chloride (75-36-5) → Acetic acid (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-2-enyl)-nona-2,4,6,8-tetraenyl ester (53250-57-0)

Guidance literature:

Multistep reaction; (i) CH₂N₂, (ii) LiAlH₄, (iii) /BRN= 605303/, Py;

DOI:10.1002/jlcr.2580130113

upstream raw materials:

α-ionone

methylmagnesium bromide

dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate

Downstream raw materials:

Acetic acid (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-2-enyl)-nona-2,4,6,8-tetraenyl ester

Refernces