Triacetylresveratrol

Base Information

• Chemical Name: Triacetylresveratrol
• CAS No.: 42206-94-0
• Molecular Formula: C20H18O6
• Molecular Weight: 354.359
• Hs Code.: 2918990090
• European Community (EC) Number: 695-560-1
• DSSTox Substance ID: DTXSID50873903
• Nikkaji Number: J711.381A,J3.571.110D
• Metabolomics Workbench ID: 174421
• ChEMBL ID: CHEMBL597744
• Mol file: 42206-94-0.mol

Synonyms:3,5,4'-tri-O-acetylresveratrol

Chemical Property of Triacetylresveratrol

Chemical Property:

• Appearance/Colour: Off white powder
• Vapor Pressure: 2.57E-10mmHg at 25°C
• Refractive Index: 1.599
• Boiling Point: 504.8 °C at 760 mmHg
• Flash Point: 221.5 °C
• PSA: 78.90000
• Density: 1.241 g/cm³
• LogP: 3.63290
• Storage Temp.: room temp
• Solubility.: DMSO: ≥18mg/mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 354.11033829
• Heavy Atom Count: 26
• Complexity: 508

Purity/Quality:

99% ^*data from raw suppliers

trans-Resveratrol Triacetate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 37/38-41-43-50/53
• Safety Statements: 26-36/37/39-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC=C(C=C1)C=CC2=CC(=CC(=C2)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)OC(=O)C)OC(=O)C
• Description: Triacetyl resveratrol (CAS 42206-94-0) is a resveratrol prodrug. One method for increasing the half-life of resveratrol?in vivo?is acetylation of the phenolic OH groups. Deacetylation takes place?in vivo?or in intact cells via the action of intracellular esterases releasing active resveratrol.
• Uses: trans-Resveratrol Triacetate is the acetylated analogue of Resveratrol (R150000) that is a natural antioxidant and a potential radioprotective agent. trans-Resveratrol Triacetate induces p53 activity and inhibits proliferation in breast and prostate tumor cell lines. trans-Resveratrol Triacetate is the acetylated analogue of Resveratrol (R150000) that is a natural antioxidant and a potential radioprotective agent. trans-Resveratrol Triacetate induces p53 activity and inhibits proliferation in breast and prostate tumor cell lines.

Technology Process of Triacetylresveratrol

There total 35 articles about Triacetylresveratrol 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: 94.0%

4-bromophenyl acetate (1927-95-3) + 5-vinyl-1,3-phenylene diacetate (155222-48-3) → triacetyl-trans-resveratrol (42206-94-0)

Guidance literature:

With potassium carbonate; acetophenon-oxim derived palladium catalyst (CAS No_. 32679-19-9); In 1-methyl-pyrrolidin-2-one; at 150 ℃; for 3h; Product distribution / selectivity;

Reference yield: 88.2%

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) + acetyl chloride (75-36-5) → triacetyl-trans-resveratrol (42206-94-0)

Guidance literature:

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol; With dmap; triethylamine; In dichloromethane; at 10 ℃;

acetyl chloride; In dichloromethane; at 10 ℃; for 1h;

DOI:10.3390/molecules200916933

Reference yield: 75.0%

4-bromophenyl acetate (1927-95-3) + acetic anhydride (108-24-7) + 5-vinyl-1,3-phenylene diacetate (155222-48-3) → triacetyl-trans-resveratrol (42206-94-0)

Guidance literature:

4-bromophenyl acetate; 5-vinyl-1,3-phenylene diacetate; With sodium hydrogencarbonate; palladium diacetate; tris-(o-tolyl)phosphine; In DMF (N,N-dimethyl-formamide); at 100 ℃; for 18h;

acetic anhydride; With pyridine; In ethyl acetate; at 80 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

acetic anhydride

acetyl chloride

4-acetoxyiodobenzene

Downstream raw materials:

resveratrol

resveratrol trimethacrylate

Resveratrol-3-O-glucuronide

(E)-4-(3-acetoxy-5-hydroxystyryl)phenyl acetate

Refernces

• 1、 Liu, Qing,Kim, Cheong Taek,Jo, Yang Hee,Kim, Seon Beom,Hwang, Bang Yeon,Lee, Mi Kyeong. "Synthesis and biological evaluation of resveratrol derivatives as melanogenesis inhibitors". . p. 16933 - 16945. Retrieved 2015.
• 2、 Danylec, Basil,Campi, Eva M.,Forsyth, Craig M.,Boysen, Reinhard I.,Hearn, Milton T. W.. "Photochemically Induced Solid State Dimerisation of Resveratrol Analogues: A Greener Synthetic Process". . p. 1260 - 1270. Retrieved 2020/10/06.
• 3、 -. "Resveratrol triacetate continuous preparation method (by machine translation)". Paragraph 0018-0039. . Retrieved 2019/03/08.