all-trans-18-Hydroxyretinoic acid

Base Information

• Chemical Name: all-trans-18-Hydroxyretinoic acid
• CAS No.: 63531-93-1
• Molecular Formula: C20H28O3
• Molecular Weight: 316.4345
• UNII: REU22CK3HJ
• DSSTox Substance ID: DTXSID501313930
• Nikkaji Number: J362.533H
• Wikidata: Q27149702
• Metabolomics Workbench ID: 72186
• Mol file: 63531-93-1.mol

Synonyms:18-Hydroxyretinoic acid;all-trans-18-Hydroxyretinoic acid;63531-93-1;all-trans-18-Hydroxy Retinoic Acid;18-hydroxy-all-trans-retinoic acid;(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohexen-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid;Ro 12-4825;(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid;all-trans-9-(2-(Hydroxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid;18-hydroxy-all-trans-retinoate;Retinoic acid, 18-hydroxy-;2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(6,6-dimethyl-2-(hydroxymethyl)-1-cyclohexen-1-yl)-, (E)-;SCHEMBL7132816;CHEBI:80657;DTXSID501313930;rac-18-hydroxy-all-trans-retinoate;LMPR01090054;rac-18-hydroxy-all-trans-retinoic acid;Q27149702

Chemical Property of all-trans-18-Hydroxyretinoic acid

Chemical Property:

• Vapor Pressure: 9.98E-13mmHg at 25°C
• Boiling Point: 514.3°C at 760 mmHg
• Flash Point: 278.9°C
• PSA: 57.53000
• Density: 1.069g/cm³
• LogP: 4.57500
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 316.20384475
• Heavy Atom Count: 23
• Complexity: 584

Purity/Quality:

98% ^*data from raw suppliers

all-trans-18-HydroxyRetinoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC=CC(=CC(=O)O)C)C=CC1=C(CCCC1(C)C)CO
• Isomeric SMILES: C/C(=C\C=C\C(=C\C(=O)O)\C)/C=C/C1=C(CCCC1(C)C)CO
• Uses: all-trans-18-Hydroxy Retinoic Acid is hydroxylated metabolite of all-trans-Retinoic Acid (R250200) produce by cytochrome P450, CYP26C1.

Technology Process of all-trans-18-Hydroxyretinoic acid

There total 16 articles about all-trans-18-Hydroxyretinoic 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: 79.0%

(2E,4E,6E,8E)-9-[2-(1-Ethoxy-ethoxymethyl)-6,6-dimethyl-cyclohex-1-enyl]-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid (81121-51-9) → 18-Hydroxyretinoic acid (63531-93-1)

Guidance literature:

With sulfuric acid; In acetone; for 0.5h; Ambient temperature;

DOI:10.1021/jo00348a043

Reference yield: 15.0%

ethyl (2E,4E,6E,8E)-9-<2-(acetoxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl>-3,7-dimethyl-2,4,6,8-nonatetraenoate (81176-71-8) → 18-Hydroxyretinoic acid (63531-93-1) + (3E,5E,7Z)-8-(7,7-Dimethyl-1,3,4,5,6,7-hexahydro-isobenzofuran-1-yl)-3,7-dimethyl-octa-3,5,7-trienoic acid (81132-94-7)

Guidance literature:

With potassium hydroxide; In methanol; water; for 0.5h; Heating;

DOI:10.1021/jo00348a043

Reference yield:

6-isopropoxymethylene-2,2-dimethyl-cyclohexanone (65519-73-5) → 18-Hydroxyretinoic acid (63531-93-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-butyllithium / 1.) THF, hexane, -65 - 0 deg C, 2.) -65 deg C up to room temp., 1 h

2: 1 N H₂SO₄ / acetone / 0.5 h

3: LiAlH₄ / diethyl ether / 3 h / Ambient temperature

4: pyridine / diethyl ether / 2 h / Ambient temperature

5: 99 percent / CH₂Cl₂ / 1 h / Ambient temperature

6: sodium methoxide / CH₂Cl₂; methanol / 0.17 h / 0 - 5 °C

7: triethylamine / bis(benzonitrile)palladium dichloride / acetonitrile / 1 h / Ambient temperature

8: potassium hydroxide / methanol; H₂O / 0.5 h / Heating

With pyridine; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; sulfuric acid; sodium methylate; triethylamine; bis(benzonitrile)palladium(II) dichloride; In methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jo00348a043

upstream raw materials:

(2E,4E,6E,8E)-9-[2-(1-Ethoxy-ethoxymethyl)-6,6-dimethyl-cyclohex-1-enyl]-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid

ethyl (2E,4E,6E,8E)-9-<2-(acetoxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl>-3,7-dimethyl-2,4,6,8-nonatetraenoate

6-isopropoxymethylene-2,2-dimethyl-cyclohexanone

2-formyl-6,6-dimethylcyclohexanone

Refernces

• 1、 Rosenberger, Michael,Neukom, Christian. "Retinoic Acid Metabolites. 3. Total Synthesis of (2E,4E,6E,8E)-3,7-Dimethyl-9--2,4,6,8-nonatetraenoic Acid". . p. 1782 - 1785. Retrieved 2007/10/02.