Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester

Base Information

• Chemical Name: Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester
• CAS No.: 166584-42-5
• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.51
• Mol file: 166584-42-5.mol

Synonyms:Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester

Chemical Property of Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester

There total 2 articles about Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl 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: 63.0%

Retinol acetate (127-47-9,64536-04-5) → Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester (166584-42-5) + Acetic acid (3E,5E,7E)-(1S,2S)-2-hydroxy-1-hydroxymethyl-2,6-dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trienyl ester

Guidance literature:

With potassium osmate(VI); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 0 ℃; for 4h; Yields of byproduct given;

DOI:10.1016/0040-4039(95)00774-7

Reference yield:

Retinol acetate (127-47-9,64536-04-5) → Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester (166584-42-5)

Guidance literature:

With potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III); potassium osmate(VI); In tert-butyl alcohol;

DOI:10.1021/jm049080y

Reference yield:

Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester (166584-42-5) → (4E,6E,8E)-(2S,3S)-9-(2,6-Dimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-4,6,8-triene-1,2,3-triol

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; In methanol;

DOI:10.1021/jm049080y

upstream raw materials:

Retinol acetate

Downstream raw materials:

Acetic acid (3E,5E,7E)-(1S,2S)-1-acetoxymethyl-2-hydroxy-2,6-dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trienyl ester

(3E,5E,7E)-(R)-3,7-Dimethyl-9-[2,6,6-trimethyl-cyclohex-2-en-(E)-ylidene]-nona-3,5,7-triene-1,2-diol

Acetic acid (2E,4E,6E)-(R)-1-acetoxymethyl-2,6-dimethyl-8-[2,6,6-trimethyl-cyclohex-2-en-(E)-ylidene]-octa-2,4,6-trienyl ester

Refernces

• 1、 Simoni, Daniele,Giannini, Giuseppe,Roberti, Marinella,Rondanin, Riccardo,Baruchello, Riccardo,Rossi, Marcello,Grisolia, Giuseppina,Invidiata, Francesco Paolo,Aiello, Stefania,Marino, Silvia,Cavallini, Sabrina,Siniscalchi, Anna,Gebbia, Nicola,Crosta, Lucia,Grimaudo, Stefania,Abbadessa, Vincenzo,Di Cristina, Antonietta,Tolomeo, Manlio. "Studies on the apoptotic activity of natural and synthetic retinoids: Discovery of a new class of synthetic terphenyls that potently support cell growth and inhibit apoptosis in neuronal and HL-60 cells". . p. 4293 - 4299. Retrieved 2007/10/03.