Acetic acid [3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] ester

Base Information

• Chemical Name: Acetic acid [3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] ester
• CAS No.: 34356-31-5
• Molecular Formula: C22H32 O2
• Molecular Weight: 328.495
• European Community (EC) Number: 251-956-2
• DSSTox Substance ID: DTXSID50859247
• Wikidata: Q27166499
• Mol file: 34356-31-5.mol

Synonyms:acetic acid [3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] ester;[3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate;34356-31-5;Retinol acetate;Vitamin A acetate;9-cis-Retinol acetate;9-cis-Vitamin A acetate;Spectrum_001302;Spectrum2_000501;Spectrum3_001187;Spectrum4_000770;SCHEMBL21588;KBioGR_001160;KBioSS_001782;DivK1c_000522;SPBio_000421;KBio1_000522;KBio2_001782;KBio2_004350;KBio2_006918;KBio3_002333;DTXSID50859247;NINDS_000522;AKOS030242267;FT-0658966;FT-0674379;Q27166499

Chemical Property of Acetic acid [3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] ester

Chemical Property:

• Vapor Pressure: 5.86E-08mmHg at 25°C
• Boiling Point: 440.5°C at 760 mmHg
• Flash Point: 124.8°C
• PSA: 26.30000
• Density: 0.968g/cm³
• LogP: 6.08110
• XLogP3: 6.3
• 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:

98%Min ^*data from raw suppliers

13-cis-Retinyl Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCOC(=O)C)C)C
• Uses: 13-cis-Retinyl Acetate is a derivative of 13-Cis-Retinol (R252110), an active metabolite of vitamin A.

Technology Process of Acetic acid [3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] ester

There total 39 articles about Acetic acid [3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] 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: 94.7%

C36H48O6S2 (414871-77-5) → ALK-001 (127-47-9,22586-94-3,29443-87-6,29444-27-7,29584-22-3,34356-31-5,63568-38-7,98462-63-6,137121-50-7,137121-51-8,137121-55-2,64536-04-5)

Guidance literature:

With methanol; potassium hydroxide; benzyltriethylammonium chloride; In di-isopropyl ether; at 30 ℃; for 16h;

Reference yield:

Retinol acetate (127-47-9,64536-04-5) → anhydroretinol (1224-78-8,7245-10-5,20603-89-8,70268-03-0,70268-04-1,70268-05-2,144407-18-1) + retinyl methyl ether (32450-56-9) + 9-cis-Vitamin-A-acetat (29584-22-3,64536-04-5) + (7E,9E,11E,13Z)-retinyl acetate (34356-31-5,64536-04-5)

Guidance literature:

In methanol; for 0.166667h; Irradiation;

DOI:10.1016/S0040-4039(00)97417-3

Reference yield:

2-cis-Vitamin-A (2052-63-3) + acetic anhydride (108-24-7) → 9-cis-retinol (68-26-8,2052-63-3,6018-74-2,17706-49-9,22737-96-8,29444-25-5,34218-73-0,39815-04-8,69686-68-6,69686-69-7,74743-94-5,84415-27-0,84415-28-1,85354-09-2,85354-10-5,93380-02-0,98462-62-5,137121-52-9,22737-97-9) + 9cis,13cis-retinyl acetate (29444-27-7,64536-04-5) + (7E,9E,11E,13Z)-retinyl acetate (34356-31-5,64536-04-5) + 11,13-di-cis-Vitamin-A-acetat (63568-38-7,64536-04-5)

Guidance literature:

With triethylamine; In hexane; Yield given;

DOI:10.1246/cl.1985.1883

upstream raw materials:

C₃₆H₄₈O₆S₂

(E)-4-acetoxy-2-methylcrotonaldehyde

[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

pyridine

Downstream raw materials:

(7Z,11Z)-Vitamin A

(7Z)-Vitamin A

9cis,13cis-retinyl acetate

Retinol acetate

Refernces

• 1、 Kahremany, Shirin,Kubas, Adam,Tochtrop, Gregory P.,Palczewski, Krzysztof. "Catalytic synthesis of 9-cis-retinoids: Mechanistic insights". supporting information. p. 10581 - 10595. Retrieved 2019/07/22.
• 2、 -. "Process for producing retinol and intermediate compounds for producing the same". Page 14. . Retrieved 2010/01/31.