(2E,4E,6Z,8E)-Ethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

Base Information

• Chemical Name: (2E,4E,6Z,8E)-Ethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
• CAS No.: 86708-67-0
• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.495
• DSSTox Substance ID: DTXSID401295432
• Mol file: 86708-67-0.mol

Synonyms:86708-67-0;(2E,4E,6Z,8E)-Ethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate;ethyl 9-cis-retinoate;SCHEMBL8571492;DTXSID401295432;Retinoic acid, ethyl ester, 9-cis-;AKOS024263178;A937335;ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate

Chemical Property of (2E,4E,6Z,8E)-Ethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

Chemical Property:

• XLogP3: 7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 328.240230259
• Heavy Atom Count: 24
• Complexity: 596

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)C=CC=C(C)C=CC1=C(CCCC1(C)C)C
• Isomeric SMILES: CCOC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(CCCC1(C)C)C
• Uses: Ethyl 9-cis-retinoate is a derivative of 9-cis-Retinoic Acid (R245000), which is an endogenous retinoic acid isomer, which is capable of binding to both retinoic acid receptors (RAR) and retinoid X receptors (RXR). A biologically active ligand for members of the RAR and RXR subfamilies, implying that it may play a critical role in regulating retinoid-responsive pathways.

Technology Process of (2E,4E,6Z,8E)-Ethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

There total 55 articles about (2E,4E,6Z,8E)-Ethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 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: 98.0%

→ ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate (86708-67-0,24519-09-3)

Guidance literature:

With copper dichloride; In ethanol; for 0.5h;

DOI:10.1021/jo961041+

Reference yield: 88.0%

(1E,3E)-3-methyl-1-[2,6,6-trimethylcyclohex-1-enyl]hexa-1,3,5-triene (43219-56-3) + ethyl (2E,4E/Z)-3-methylhexa-2,4-dienoate → ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate (86708-67-0,24519-09-3)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; at 20 ℃; for 16h; diastereoselective reaction;

DOI:10.1016/j.tetlet.2012.07.122

Reference yield: 88.0%

ethyl (2E,4E,6Z)-7-tributylstannyl-3-methyl-2,4,6-octatrienoate (256518-18-0,1106680-90-3) + (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate (303779-99-9) → ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate (86708-67-0,24519-09-3)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenyl-arsane; cesium fluoride; In N,N-dimethyl-formamide; at 45 ℃; for 1.5h;

DOI:10.1039/b813760a

upstream raw materials:

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

triethyl 3-methyl-4-phosphonocrotonate

(2E,4E,6E)-8-Acetoxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6-trienoic acid ethyl ester

ethanol

Downstream raw materials:

13-cis-retinoic acid

all-trans-retinoic-acid

7-cis-retinoic acid

ethyl (all-E)-retinoate