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Chemical Structure| 863-03-6

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Product Details of [ 863-03-6 ]

CAS No. :863-03-6
Formula : C22H18O10
M.W : 442.37
SMILES Code : O=C(O[C@H]1[C@@H](C2=CC=C(O)C(O)=C2)OC3=CC(O)=CC(O)=C3C1)C4=CC(O)=C(O)C(O)=C4
MDL No. :N/A

Safety of [ 863-03-6 ]

Application In Synthesis of [ 863-03-6 ]

* 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 [ 863-03-6 ]

[ 863-03-6 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 147506-92-1 ]
  • [ 863-03-6 ]
  • [ 1707-75-1 ]
  • 3
  • 3,4,5-Trihydroxy-benzoic acid (2R,3S)-4-carboxymethylsulfanyl-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl ester [ No CAS ]
  • [ 863-03-6 ]
  • 5
  • [ 126715-82-0 ]
  • [ 100-53-8 ]
  • [ 80044-64-0 ]
  • [ 863-03-6 ]
  • 6
  • [ 126715-92-2 ]
  • [ 100-53-8 ]
  • [ 126716-07-2 ]
  • [ 863-03-6 ]
  • 7
  • [ 79786-01-9 ]
  • [ 863-03-6 ]
  • [ 149-91-7 ]
  • malabathrin A [ No CAS ]
  • 8
  • [ 863-03-6 ]
  • [ 621-54-5 ]
  • [ 31129-95-0 ]
  • [ 6500-64-7 ]
  • [ 31129-94-9 ]
  • 9
  • [ 863-03-6 ]
  • [ 621-54-5 ]
  • [ 31129-95-0 ]
  • [ 31129-94-9 ]
  • [ 111397-00-3 ]
  • 10
  • [ 863-03-6 ]
  • [ 621-54-5 ]
  • [ 31129-95-0 ]
  • [ 31129-94-9 ]
  • (4R)-5-(3-hydroxyphenyl)-γ-valerolactone [ No CAS ]
  • 11
  • [ 863-03-6 ]
  • [ 621-54-5 ]
  • [ 31129-95-0 ]
  • [ 31129-94-9 ]
  • [ 191666-22-5 ]
  • 12
  • [ 863-03-6 ]
  • [ 621-54-5 ]
  • [ 31129-95-0 ]
  • [ 31129-94-9 ]
  • 2'',3''-dihydroxyphenoxyl (3',4'-dihydroxyphenyl)propionate [ No CAS ]
  • 13
  • [ 863-03-6 ]
  • [ 621-54-5 ]
  • [ 31129-95-0 ]
  • [ 31129-94-9 ]
  • (2S)-1-(3'-hydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol [ No CAS ]
  • 14
  • [ 863-03-6 ]
  • [ 621-54-5 ]
  • [ 31129-95-0 ]
  • [ 31129-94-9 ]
  • [ 490-46-0 ]
  • 15
  • [ 485-80-3 ]
  • [ 863-03-6 ]
  • [ 108907-44-4 ]
  • 16
  • [ 108-98-5 ]
  • C113H100O62 [ No CAS ]
  • [ 863-03-6 ]
  • [ 402493-24-7 ]
YieldReaction ConditionsOperation in experiment
With water;porcine liver esterase; at 37℃; for 0.166667h;Reactivity; Example 3 - Esterase resistance of compound of example 1; The product of example 1 was tested for in esterase sensitivity as compared to EGG using commercially available porcine liver esterase (Sigma). EGG was totally hydrolysed to 10 min at 37C whereas the compound of example 1 was not affected in this time.
  • 18
  • [ 100-53-8 ]
  • rhatannin [ No CAS ]
  • [ 37064-35-0 ]
  • [ 80418-27-5 ]
  • [ 863-03-6 ]
  • [ 154-23-4 ]
  • 19
  • [ 147506-92-1 ]
  • [ 863-03-6 ]
  • [ 1707-75-1 ]
  • (-)-epicatechin gallate radical [ No CAS ]
  • 20
  • [ 52-89-1 ]
  • polymeric flavan-3-ol, Vitis vinifera [ No CAS ]
  • [ 863-03-6 ]
  • 4β-(S-L-cysteinyl)-(+)-catechin [ No CAS ]
  • 4β-(S-L-cysteinyl)-(-)-epicatechin [ No CAS ]
  • 4β-(S-cysteinyl)epicatechin 3-O-gallate [ No CAS ]
  • 22
  • [ 18162-48-6 ]
  • [ 863-03-6 ]
  • [ 853687-37-3 ]
YieldReaction ConditionsOperation in experiment
91% With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃; Example 1A (-)-ECG-7TBSTBS; To a solution of <strong>[863-03-6](-)-epicatechin gallate</strong> 1 (2.0g, 4.4mmol), in DMF(10ml_) at 0C was added imidazole (3.0g, 0.044mol) followed by tert-butyldimethylsilyl chloride (6.6g, 0.044mol) and the mixture was allowed towarm to room temperature overnight. On completion of reaction the mixturewas diluted with water (20mL). The product was then partitioned betweenether (2x 20mL) and water (20ml_). The organics were then combined, driedwith MgS04, filtered and concentrated in vacua to yield a colourless oil whichwas purified by flash chromatography (eluting with 5% Et20: Pet Ether) togive the product 2 as a colourless oil, 5.0g, 91%; 6H (400MHz, CDCI3) 0.08-0.21 (m, 42H, 7x OSi(CH3)2C(CH3)3), 0.90- 0.98 (m, 63H, 7xOSi(CH3)2C(CH3)3), 2.97 (d, 2H, J3.1, ArCH2CHCHO), 5.05 (s, 1H,ArCH2CHCHO), 5.56 (m, 1H, ArCH2CHCHO), 5.96 (d, 1H, J2.3, ArH), 6.18(d, 1H, J 2.3, ArH), 6.74 (d, 1H, J 8.7, ArH), 6.89 (d, 1H, J 2.1, ArH) 6.95 (dd,1H, J8.3, 2.1, ArH), 7.09 (s, 2H, 2x ArH); 5C (100MHz, CDCI3)-4.4, -4.3, -4.2-4.1, -3.9, -3.7, 18.1, 18.2, 18.3, 18.4, 18.8, 25.7, 25.8, 25.9, 26.1, 26.7,68.0, 76.7, 101.7, 103.7, 103.9, 115.3, 119.3, 119.7, 120.8, 121.7, 131.1,142.9, 146.6, 148.2, 154.7, 154.9, 155.6, 165.0; MS (m/z) No mass ionobserved; [a]D -57.9 (c 1.0, CHCI3, at 25C).
  • 23
  • [ 863-03-6 ]
  • (-)-(2R,3R,4R)-3,4,5,7,3',4'-hexahydroxyflavan [ No CAS ]
  • [ 490-46-0 ]
  • 24
  • [ 149-91-7 ]
  • [ 863-03-6 ]
  • theaflavate A [ No CAS ]
  • [ 34218-97-8 ]
  • [ 5146-12-3 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; ECG (0.5 g) and gallic acid (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1 :10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 20 mg epitheaflavic acid 3-gallate, 40 theaflavate A and 10 mg purpurogallin carboxylic acid were obtained. [0112] 1H NMR (CD3OD, 600 MHz): deltaH 8.64 1H s, 7.84 1H s, 7.83 1H s, 6.83 2H s, 6.02 1H d, J=2.4 Hz, 5.98 1H d, J=2.4, 5.61 1H s, 4.37 1H, m, 3.03 1H dd, J=4.8, 16.8 Hz, 2.87 d, J=16.8 Hz; 13C NMR (CD3OD, 150 MHz): deltaC 186.5, 170.1, 167.1, 158.0, 156.9, 155.1, 151.7, 148.9, 146.2, 139.8, 132.8, 131.6, 126.8, 122.6, 122.5, 120.8, 116.3, 110.0, 99.3, 96.9, 96.0, 75.7, 68.6, 27.2 ppm.
  • 25
  • [ 863-03-6 ]
  • [ 2596-50-1 ]
  • [ 30462-35-2 ]
YieldReaction ConditionsOperation in experiment
10% With polyphenol oxidase; In aq. phosphate buffer; for 2.0h;pH 6.0;Enzymatic reaction; Ina typical experiment, EC (290 mg) and EGC (306 mg) were added to a mixture of acetone and phosphate buffer (pH 6.0) (1:10 v/v,100 ml), C. sinensis cell culture (50 ml including 10.2 g cells), and 3% H2O2 (0.8 ml). The mixture was stirred for 4 min and thenextracted using CH3COOEt. Further, the organic layer was driedover anhydrous MgSO4 and concentrated in vacuo to provide TF(395 mg) with 70% yield and 100% conversion. In the HPLC analysis,12 peaks for EC and ECG were virtually absent, but a peak for TF was observed.
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; ECG (1 g) and EGCG (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 4 mg horseradish peroxidase. While being stirred, 2.0 ml of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 ml×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 100 mg theaflavin 3,3'-digallate was obtained. [0088] 1H NMR (CD3OD, 600 MHz): deltaH 7.79 1H s, 7.76 1H s, 7.47 1H s, 6.88 2H s, 6.80 2H s, 6.07 1H d, J=2.4 Hz, 6.03 2H d, J=2.4 Hz, 6.00 1H d, J=2.4 Hz, 5.86 1H brs, 5.76 1H m, 5.67 1H m, 5.21 1H s, 3.17 1H dd, J=4.8, 16.8 Hz, 3.09 1H dd, J=4.8, 17.4, 2.91 2H m.
polyphenol oxidase; at 20℃; for 6.0h;pH 5.0;Phosphate-citrate buffer; Enzymatic reaction; EC (1 g, 3.5 mmol) and EGC (1 g, 3.3 mmol) were dissolved into the 200 mL of phosphate-citrate buffer (50 mM, pH 5.0) along with 2 g of crude PPO enzyme. The enzymatic oxidation was carried out at room temperature for 6 hour with stirring. The reaction solution was then subjected to fractionation with the same volume of ethyl acetate with three times. Then, the organic layer was concentrated under reduced pressure. The resulting residues were subjected to Sephadex LH-20 column chromatography eluting with gradient of ethanol to 20% of acetone in ethanol. Among the collected 14 fractions (each c.a. 90 mL), 810 fractions were combined, and concentrated under reduced pressure. The resulting residue was subjected to further purification on a RP-18 silica gel column eluting with gradient of 40%50% of aqueous methanol. During elution, 38 fractions (each c.a. 13 mL) were received. Among them, 1017 fractions were combined, and concentrated under reduced pressure, and were subjected to freeze-drying. It yielded deep-reddish color of compound 1 (280 mg). Along with the same enzyme reaction and isolation procedure, compound 2 was obtained from EC and EGCG reaction. The enzymatic oxidation of EGC and ECG, ECG and EGCG reaction yielded compound 3 and compound 4, respectively.
With tyrosinase from mushroom Agaricus bisporus; In aq. phosphate buffer; ethanol; at 25℃; for 0.5h;pH 6.0;Enzymatic reaction;Kinetics; General procedure: Unless otherwise specified, enzymatic reactions were performed using tyrosinase at 0.05mg/mL (156mU/mL) with each catechin and 0.1mg/mL (313 mU/mL) for TF synthesis in 50mM Na-phosphate buffer, pH 6.0, at 25C without pH control. Respective catechin solutions (10mM) were prepared using 20% ethanol/40mM Na-phosphate buffer, pH 6.0. After certain incubation periods, an aliquot (100muL) of the reaction mixture was collected and added into 1mL of 25mM citric acid solution (pH 2.4) to stop the reaction. These samples were cooled in an autosampler (L-2200, Hitachi, Tokyo) at 5-8C and analyzed by RP-HPLC, which was carried out using a Hitachi HPLC system (L-2130 pump, L-2400 UV detector) equipped with a SUS line filter (GL Science, Tokyo, Japan) and a Phenomenex SynergiTM 4mum Polar-RP 80 (4.6mm×150mm) column (Shimadzu GLC, Tokyo, Japan). Catechins were eluted using an aqueous 20% MeCN solution containing 0.05% phosphoric acid at flow rate of 1mL/min, and detected at 280nm. For TF1, TF2A, TF2B, and TF3, aqueous 32% MeCN solutions containing 0.05% phosphoric acid were used as eluents, and each retention time (tR) was identified using the TF standards, which were obtained as described previously [31]. The analysis of chromatograms was performed with the data processing software Chromato-PRO (Run Time Corporation, Tokyo, Japan).

  • 26
  • [ 863-03-6 ]
  • [ 490-46-0 ]
  • theaflavate B [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; EC (0.5 g) and ECG (0.5 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 200 mg theaflavate B was obtained. [0100] 1H NMR (CD3OD, 600 MHz): deltaH 8.26 1H s, 7.88 1H s, 7.59 1H s, 6.87 1H dd, J=1.8, 7.8 Hz, 6.86 1H d, J=1.8 Hz, 6.55 1H d, J=7.8 Hz, 6.16 1H d, J=2.4 Hz, 6.08 1H d, J=2.4, 6.05 1H d, J=2.4 Hz, 5.98 1H, d, J=2.4 Hz, 5.66 1H brs, 5.46 1H brs, 5.08 1H s, 4.14 1H brs, 3.34 dd, J=4.8, 16.8 Hz, 3.21 dd, J=4.8, 16.8 Hz, 3.17 dd, J=3.6, 16.2 Hz, 2.88 d, J=16.8; 13C NMR (CD3OD, 150 MHz): deltaC 186.4, 167.8, 158.3, 158.0, 157.9, 157.7, 157.4, 157.1, 154.9, 151.8, 149.5, 146.3, 146.0, 134.8, 132.3, 131.3, 126.5, 124.4, 123.7, 122.4, 119.2, 116.3, 115.8, 114.4, 100.7, 99.5, 97.2, 97.1, 96.6, 96.5, 78.1, 77.0, 72.1, 66.7, 30.0, 26.7 ppm.
  • 27
  • [ 863-03-6 ]
  • [ 154-23-4 ]
  • neotheaflavate B [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; C (0.5 g) and ECG (0.5 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 ml of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 ml×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 90 mg neotheaflavate B was obtained. [0103] 1H NMR (CD3OD, 600 MHz): deltaH 8.77 1H s, 7.64 1H s, 7.61 1H s, 6.88 1H d, J=1.8 Hz, 6.82 1H dd, J=1.8, 8.4 Hz, 6.64 1H d, J=8.4 Hz, 6.03 1H d, J=2.4 Hz, 5.98 1H d, J=2.4, 5.96 2H brs, 5.58 1H brs, 5.38 1H brd, J=7.2 Hz, 5.04 1H s, 4.07 1H m, 3.03 dd, J=4.8, 16.8 Hz, 2.95 brd, J=16.8, 2.91 dd, J=4.8, 16.8 Hz, 2.66 dd, J=3.6, 16.2 Hz; 13C NMR (CD3OD, 150 MHz): deltaC 186.6, 167.7, 157.9, 157.7, 157.3, 157.0, 156.8, 154.7, 152.3, 149.8, 146.0, 145.8, 135.0, 134.3, 131.2, 128.8, 124.0, 122.5, 119.0, 116.2, 115.8, 114.4, 101.2, 99.2, 97.0, 96.8, 96.1, 95.9, 79.7, 78.0, 72.0, 69.6, 29.6, 26.6 ppm.
  • 28
  • [ 863-03-6 ]
  • [ 970-73-0 ]
  • [ 28543-07-9 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; ECG (1 g) and EGC (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 4 mg horseradish peroxidase. While being stirred, 2.0 ml of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 ml×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 110 mg theaflavin 3'-gallate was obtained. [0085] 1H NMR (CD3OD, 600 MHz): deltaH 7.88 1H s, 7.87 1H s, 7.37 1H s, 6.84 2H s, 6.06 d, J=2.4 Hz, 6.00 1H d, J=2.4 Hz, 5.98 1H d, J=2.4 Hz, 5.97 d, J=2.4 Hz, 5.87 brs, 5.81 1H brd J=3.0 Hz, 4.94 1H brs, 4.33 1H brs, 3.09 1H dd, J=4.8, 17.4 Hz, 2.96 1H dd, J=4.8, 16.8, 2.88 1H brd, J=17.4 Hz, 2.86 dd, J=2.4, 16.8 Hz; 13C NMR (CD3OD, 150 MHz): deltaC 185.6, 167.2, 158.0, 157.9, 157.8, 157.7, 157.0, 156.6, 156.0, 155.5, 151.1, 146.2, 139.7, 134.8, 130.3, 128.8, 125.9, 123.0, 121.9, 120.9, 118.3, 99.8, 99.6, 96.8, 96.7, 95.8, 95.7, 81.2, 75.8, 68.3, 66.5, 29.3, 27.2 ppm.
With tyrosinase from mushroom Agaricus bisporus; In aq. phosphate buffer; ethanol; at 25℃; for 0.5h;pH 6.0;Enzymatic reaction;Kinetics; General procedure: Unless otherwise specified, enzymatic reactions were performed using tyrosinase at 0.05mg/mL (156mU/mL) with each catechin and 0.1mg/mL (313 mU/mL) for TF synthesis in 50mM Na-phosphate buffer, pH 6.0, at 25C without pH control. Respective catechin solutions (10mM) were prepared using 20% ethanol/40mM Na-phosphate buffer, pH 6.0. After certain incubation periods, an aliquot (100muL) of the reaction mixture was collected and added into 1mL of 25mM citric acid solution (pH 2.4) to stop the reaction. These samples were cooled in an autosampler (L-2200, Hitachi, Tokyo) at 5-8C and analyzed by RP-HPLC, which was carried out using a Hitachi HPLC system (L-2130 pump, L-2400 UV detector) equipped with a SUS line filter (GL Science, Tokyo, Japan) and a Phenomenex SynergiTM 4mum Polar-RP 80 (4.6mm×150mm) column (Shimadzu GLC, Tokyo, Japan). Catechins were eluted using an aqueous 20% MeCN solution containing 0.05% phosphoric acid at flow rate of 1mL/min, and detected at 280nm. For TF1, TF2A, TF2B, and TF3, aqueous 32% MeCN solutions containing 0.05% phosphoric acid were used as eluents, and each retention time (tR) was identified using the TF standards, which were obtained as described previously [31]. The analysis of chromatograms was performed with the data processing software Chromato-PRO (Run Time Corporation, Tokyo, Japan).
  • 29
  • [ 863-03-6 ]
  • theaflavate A [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; for 0.5h;pH 5.0;Enzymatic reaction; ECG (0.85 g) was dissolved in pH 5 buffer (1:10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 1.5 mL of 3.13% H2O2 was added three times during 30 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 60 mg theaflavate A was obtained and 600 mg ECG was recovered. [0097] 1 H NMR (CD3OD, 600 MHz): deltaH 8.33 1H s, 7.81 1H s, 7.65 1H s, 6.87 1H dd, J=1.8, 7.8 Hz, 6.85 1H d, J=1.8 Hz, 6.80 2H, s,6.53 1H d, J=7.8 Hz, 6.15 1H d, J=2.4 Hz, 6.11 1H d, J=2.4, 6.09 1H d, J=2.4 Hz, 5.98 1H, d, J=2.4 Hz, 5.69 1H brs, 5.64 1H brs, 5.52 1H, brd, J=3.6Hz, 5.11 1H s,3.32 dd, J=4.8, 18.0Hz, 3.10 dd, J=4.8, 18.0Hz, 3.05 dd, J=1.8, 16.8 Hz, 2.91 d, J=16.8; 13C NMR (CD3OD, 150 MHz): deltaC 186.8, 167.8, 167.3, 158.2, 158.1, 158.0, 157.9, 157.2, 157.1, 155.3, 149.5, 146.4, 146.3, 146.0, 140.0, 133.5, 131.2, 126.6, 124.8, 122.9, 122.6, 121.0, 119.0, 116.4, 115.8, 114.2, 110.2, 100.0, 99.4, 97.3, 97.2, 96.5, 96.4, 78.0, 75.6, 72.1, 68.9, 27.3, 26.7 ppm.
  • 30
  • [ 863-03-6 ]
  • (-)-(2R,3R,4R)-3,4,5,7,3',4'-hexahydroxyflavan [ No CAS ]
  • 31
  • [ 63604-98-8 ]
  • [ 863-03-6 ]
  • 32
  • [ 1486-48-2 ]
  • [ 863-03-6 ]
  • 33
  • [ 1486-47-1 ]
  • [ 863-03-6 ]
  • 34
  • [ 20728-73-8 ]
  • [ 863-03-6 ]
  • 35
  • [ 87292-49-7 ]
  • [ 863-03-6 ]
 

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