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Chemical Structure| 42206-94-0 Chemical Structure| 42206-94-0
Chemical Structure| 42206-94-0

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Triacetylresveratrol is a prodrug of resveratrol with multiple targets including sirt, COX, IKK β and LOX, etc..

Synonyms: Triacetylresveratrol; Resveratrol triacetate; 3,5,4'-Tri-O-acetylresveratrol

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Product Details of Acetyl-trans-resveratrol

CAS No. :42206-94-0
Formula : C20H18O6
M.W : 354.35
SMILES Code : O=C(OC1=CC=C(C=C1)/C=C/C2=CC(OC(C)=O)=CC(OC(C)=O)=C2)C
Synonyms :
Triacetylresveratrol; Resveratrol triacetate; 3,5,4'-Tri-O-acetylresveratrol
MDL No. :MFCD01546481
InChI Key :PDAYUJSOJIMKIS-SNAWJCMRSA-N
Pubchem ID :5962587

Safety of Acetyl-trans-resveratrol

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H318-H335-H410
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P362+P364-P403+P233-P501
Class:9
UN#:3077
Packing Group:

Application In Synthesis of Acetyl-trans-resveratrol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 42206-94-0 ]

[ 42206-94-0 ] Synthesis Path-Downstream   1~2

  • 2
  • [ 2628-16-2 ]
  • [ 35354-29-1 ]
  • [ 42206-94-0 ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine;; thionyl chloride;palladium diacetate; In ethyl acetate; N,N-dimethyl-formamide; toluene; (E)-3,4',5-Triacetoxystilbene 3,5-Diacetoxybenzoic acid (8.022 g, 33.706 mmol) suspended in a mixture of toluene (130 mL), DMF (500 μL) and thionyl chloride (16.00 mL, 220.6 mmol) was heated at 100 C. for three hours under an argon gas atmosphere. The solvents were removed by vacuum distillation and the residue re-suspended in toluene (85 mL) and sonicated under vacuum to remove dissolved gases. 4-Acetoxystyrene (5.74 mL, 37.5 mmol), N-ethylmorpholine (4.31 mL, 33.9 mmol) and palladium diacetate (35 mg, 0.16 mmol, 0.46 mole %) were added and the reaction heated to reflux for 2 hours. Further palladium diacetate (116 mg, 0.52 mmol, 1.54 mole %) was added and the reaction left to reflux overnight. On return to room temperature, ethyl acetate (500 mL) was added, the solution was washed with 0.1 M HCl (2*300 mL) and water (300 mL) and then dried and evaporated to return a brown solid. Purification with column chromatography (isocratically eluted with 2:1 Et2O/hexane) gave 7.888 g of a white solid, shown by 1H NMR to be predominantly the desired adduct. Further chromatography (gradient eluted starting with 4:1 hexane/EtOAc and finishing with 2:1 hexane/EtOAc) returned pure (E)-3,4',5-triacetoxystilbene (6.071 g, 51%) as a white solid. Rf 0.29 (2:1 hexane/EtOAc); mp 112.5-113.0 C. (lit mp 116 C.); (δC (CDCl3) 2.27 (s, 9H, 3*OAc), 6.80 (pseudo t, 1H, J 2.1, 4'-H), 6.93 (d, 1H, J 16.3, Htrans), 7.03 (d, 1H, J 16.3, Htrans), 7.04-7.09 (m, 4H, 3-H, 5-H, 2'-H, 6'-H) and 7.44-7.47 (m, 2H, 2-H, 6-H); δC(CDCl3) 20.07, 113.39, 115.88, 120.88, 126.19, 126.64, 128.64, 133.45, 138.53, 149.46, 150.34, 167.91 and 168.30; m/z (ESI) 377 (MNa+, 100%), 378 (21).
 

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