rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid

Base Information

• Chemical Name: rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid
• CAS No.: 81121-27-9
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424
• Mol file: 81121-27-9.mol

Synonyms:rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid

Chemical Property of rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid

There total 26 articles about rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic 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: 7.0%

(2E,4E,6E,8E)-9-(6-Hydroxymethyl-2,6-dimethyl-3-oxo-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid methyl ester (81121-36-0) → rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid (81121-27-9) + (2E,4E,6E)-8-(3a,7-Dimethyl-6-oxo-1,3,3a,4,5,6-hexahydro-isobenzofuran-1-yl)-3,7-dimethyl-octa-2,4,6-trienoic acid (81121-37-1)

Guidance literature:

With sodium hydroxide; In methanol; for 2.7h; Ambient temperature;

DOI:10.1021/jo00348a042

Reference yield:

4-ketoretinoic acid (38030-57-8,71748-58-8,100897-08-3,112924-95-5,150737-18-1,150737-19-2) → rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid (81121-27-9)

Guidance literature:

With rat reductase; NADPH; In aq. phosphate buffer; at 37 ℃; Kinetics; Enzymatic reaction;

DOI:10.1124/mol.117.111039

Reference yield:

2-acetylpropanoic acid ethyl ester (609-14-3) → rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid (81121-27-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) a) NaH, b) n-BuLi / 1.) a) THF, 0 deg C, 1.5 h, b) hexane, 0 deg C, 1.25 h, 2.) -70 deg C, 1 h

2: 54 percent / methanesulfonic acid / acetic acid / 5.5 h / Ambient temperature

3: 1.) sodium methoxide / 2.) room temp., 16 h

4: 83 percent / sodium borohydride / methanol / 3 h / Ambient temperature

5: p-toluenesulfonic acid / tetrahydrofuran / 1 h / Ambient temperature

6: 68 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 2 h / -20 - 0 °C

7: pyridine / 1 h / Ambient temperature

8: 72 percent / aq. H₂SO₄ / acetone / 1.5 h / Ambient temperature

9: 70 percent / manganese dioxide / CH₂Cl₂ / 5 h / Ambient temperature

10: 69 percent / sodium hydroxide / methanol; H₂O / 0.5 h / Ambient temperature

11: 6.56 g / manganese dioxide / CH₂Cl₂ / 2 h / Ambient temperature

12: 1.) NaCN, acetic acid, 2.) MnO₂ / room temp., 17 h

13: 54 percent / 3 N aq. NaOH / methanol / 2.7 h / Ambient temperature

With manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; methanesulfonic acid; sulfuric acid; sodium cyanide; sodium methylate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetic acid; acetone;

DOI:10.1021/jo00348a042

upstream raw materials:

(2E,4E,6E,8E)-9-(6-Hydroxymethyl-2,6-dimethyl-3-oxo-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid methyl ester

2-acetylpropanoic acid ethyl ester

2E,4E,6E-2,6-Dimethyl-7-ethoxycarbonyl-2,4,6-heptatrienal

3-((1E,3E,5E,7E)-9-Hydroxy-3,7-dimethyl-nona-1,3,5,7-tetraenyl)-4-hydroxymethyl-2,4-dimethyl-cyclohex-2-enone

Refernces

• 1、 Shimshoni, Jakob A.,Roberts, Arthur G.,Scian, Michele,Topletz, Ariel R.,Blankert, Sean A.,Halpert, James R.,Nelson, Wendel L.,Isoherranen, Nina. "Stereoselective formation and metabolism of 4-hydroxy-retinoic acid enantiomers by cytochrome p450 enzymes". . p. 42223 - 42232. Retrieved 2013/02/22.