9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid ethyl ester

Base Information

• Chemical Name: 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid ethyl ester
• CAS No.: 54350-48-0
• Molecular Formula: C23H30O3
• Molecular Weight: 354.489
• Hs Code.: 2918992090
• Wikidata: Q27166420
• Mol file: 54350-48-0.mol

Synonyms:9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid ethyl ester;HQMNCQVAMBCHCO-UHFFFAOYSA-N;BCP31125;AKOS030228516;DB00926;FT-0653621;Q27166420;9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid ethyl ester;ethyl 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate;9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester

Chemical Property of 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid ethyl ester

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 2.22E-10mmHg at 25°C
• Melting Point: 104-105 °C
• Refractive Index: 1.544
• Boiling Point: 506.4 °C at 760 mmHg
• Flash Point: 219.4 °C
• PSA: 35.53000
• Density: 1.006 g/cm³
• LogP: 5.64550
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Sonicated), Ethyl Acetate (Slightly), Met
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 354.21949481
• Heavy Atom Count: 26
• Complexity: 568

Purity/Quality:

99% ^*data from raw suppliers

Etretinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)C=CC=C(C)C=CC1=C(C(=C(C=C1C)OC)C)C
• Uses: Aromatic analog of Retinoic Acid. Immunomodulator. Antipsoriatic. Aromatic analog of Retinoic Acid. Immunomodulator. Antipsoriatic
• Therapeutic Function: Antipsoriatic, Antitumor

Technology Process of 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid ethyl ester

There total 16 articles about 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid ethyl ester 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: 72.0%

diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate (41891-54-7) + 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al (69877-38-9,419534-29-5) → etretinate (54350-48-0)

Guidance literature:

diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at 0 ℃; for 0.666667h; Inert atmosphere;

5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al; In tetrahydrofuran; at -78 - 0 ℃; for 1h;

DOI:10.1002/chem.201403024

Reference yield: 60.0%

→ etretinate (54350-48-0)

Guidance literature:

Reference yield: 9.0%

Ethyl-4-hydroxy-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,5,7-trienoat (124743-96-0) → etretinate (54350-48-0) + ethyl (2E,4E,6Z,8E)-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate (69427-40-3) + ethyl (2Z,4E,6E,8E)-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate (69427-41-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1002/hlca.19890720224

upstream raw materials:

Ethyl-4-hydroxy-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,5,7-trienoat

ethyl (E)-3-formyl-2-butenoate

3-methyl-1-penten-4-yn-3-ol

2,3,5-trimethylanisole

Downstream raw materials:

(2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraen-1-ol

(2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenal

4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylbenzene)

4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylphenol)

Refernces

Cross metathesis of β-carotene with electron-deficient dienes. A direct route to retinoids

10.1016/j.tetlet.2009.06.032

The study focuses on the cross metathesis (CM) reactions of β-carotene with electron-deficient dienes, specifically using the Hoveyda second generation catalyst, to synthesize retinoids, which are compounds related to vitamin A and play a crucial role in various biological processes such as vision, reproduction, cell differentiation, and growth. The primary chemicals used in the study include β-carotene, ethyl (2E,4E/Z)-3-methylhexa-2,4-dienoate, and the Hoveyda II catalyst. The purpose of these chemicals is to undergo CM reactions, which are a type of olefin metathesis reaction that forms new carbon-carbon bonds under mild conditions, to produce retinoids like ethyl all-trans-retinoate. The study explores the regioselectivity and diastereoselectivity of these reactions, aiming to develop an effective and fast method for the preparation of retinoids for biological and structural studies.

Synthesis of C15,C14′-ring locked all-trans-β-carotene

10.1016/S0040-4039(02)00663-9

The study presents the synthesis of a C15,C14-ring locked all-trans-β-carotene analog, which is a significant compound due to its role in the production of retinoids, essential for vision and cell differentiation. The synthesis involved the use of various chemicals, including cyclohexenone-3-carboxaldehyde, diethyl(1-cyanoethyl)phosphonate, and β-ionone, which served as starting materials and reagents in the reaction sequences. Key reactions such as Wittig and HWE olefinations were employed to construct the carbon framework, with the final product being synthesized through bis-olefination with a C15 ylide bearing the ionone moiety. This unnatural β-carotene analog preserves molecular connectivity upon oxidative cleavage, which is crucial for isotopic labeling studies to determine the source of oxygen in retinal production. The synthesized compound will be used for enzymatic oxidation studies, furthering understanding of β-carotene-15,15'-dioxygenase (BCDOX), an enzyme vital for retinoid production.