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[ CAS No. 154-23-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 154-23-4
Chemical Structure| 154-23-4
Structure of 154-23-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 154-23-4 ]

CAS No. :154-23-4 MDL No. :MFCD00075649
Formula : C15H14O6 Boiling Point : -
Linear Structure Formula :- InChI Key :PFTAWBLQPZVEMU-DZGCQCFKSA-N
M.W : 290.27 Pubchem ID :9064
Synonyms :
Catechuic acid;Cianidanol;Z 7300.;Transepar;NSC 2819;KB 53;Catechinic acid;Catechin

Calculated chemistry of [ 154-23-4 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 6.0
Num. H-bond donors : 5.0
Molar Refractivity : 74.33
TPSA : 110.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 0.36
Log Po/w (WLOGP) : 1.22
Log Po/w (MLOGP) : 0.24
Log Po/w (SILICOS-IT) : 0.98
Consensus Log Po/w : 0.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.74 mg/ml ; 0.00598 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 1.66 mg/ml ; 0.00572 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.14
Solubility : 2.09 mg/ml ; 0.00719 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.5

Safety of [ 154-23-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 154-23-4 ]

* 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 [ 154-23-4 ]

[ 154-23-4 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 528-58-5 ]
  • [ 154-23-4 ]
  • 4
  • [ 77-78-1 ]
  • [ 154-23-4 ]
  • [ 51079-25-5 ]
YieldReaction ConditionsOperation in experiment
99% Dried (+)-catechiotan (1O g, 35 mmol) was dissolved in dry acetone (250 mL) under an inert atmosphere (N2) K2CO3 (38 g, 276 mmol) was added and suspended in the reaction mixture After stirring for 1 hour, dimethylsulfate (87 mg, 276 mmol) was slowly added over a period of 30 mm and the reaction mixture refluxed for 2 hours The K2CO3 was filtered off, the acetone removed under reduced pressure and the excess (CH3)2SO4 destroyed with cold ammonia (80 mL, 25% NH3/H2O, v/v) The reaction mixture was subsequently extracted with ethyl acetate (2 x 100 mL), washed with water (2 x 70 mL) and brine (70 mL), dried over MgSO4 and the solvent removed under reduced pressure The compound 3 was obtained as an off- white, amorphous solid (11 9 g, 99%)
99% General procedure: First, K2CO3 (38 g, 276 mmol, dried at 240 C overnight) was added to an anhydrous acetone solution of predried commercial <strong>[154-23-4]catechin</strong> or epi<strong>[154-23-4]catechin</strong> (10 g, 35 mmol) under nitrogen and stirred vigorously. Second, after 1 h, dimethyl sulfate ((CH3)2SO4, 87mg, 276 mmol) was slowly added over 30 min and refluxed for 2 h. Third, at ambient temperature, K2CO3 was filtered, and acetone was removed under reduced pressure, followed by the neutralization of the excess (CH3)2SO4 with cold ammonia (80 mL, 25% NH3/H2O, v/v). Next, the crude product was extracted with ethyl acetate (2 ×100 mL), washed with water (2 × 70 mL) and brine (70 mL), and dried over MgSO4, followed by solvent removal under reduced pressure. Finally, 8 or 9 was obtained as an off white,amorphous solid (99%). The characterization of the compound was in agreement with reported data [22, 23].
  • 5
  • [ 186581-53-3 ]
  • [ 108-24-7 ]
  • [ 154-23-4 ]
  • [ 480-18-2 ]
  • [ 88204-07-3 ]
  • [ 88204-08-4 ]
  • 6
  • [ 29106-49-8 ]
  • [ 490-46-0 ]
  • [ 154-23-4 ]
  • 7
  • [ 20315-25-7 ]
  • [ 37064-35-0 ]
  • [ 128837-34-3 ]
  • [ 154-23-4 ]
  • 8
  • [ 20315-25-7 ]
  • [ 35323-91-2 ]
  • sodium epicatechin-(4β)-sulphonate [ No CAS ]
  • [ 154-23-4 ]
  • 10
  • [ 154-23-4 ]
  • [ 480-18-2 ]
  • [ 12798-57-1 ]
  • [ 23567-23-9 ]
  • [ 88244-65-9 ]
  • [ 88244-66-0 ]
  • 12
  • [ 114715-46-7 ]
  • [ 20315-25-7 ]
  • [ 50562-99-7 ]
  • [ 114586-49-1 ]
  • [ 154-23-4 ]
  • 13
  • [ 20315-25-7 ]
  • [ 100-53-8 ]
  • [ 37064-35-0 ]
  • [ 128837-34-3 ]
  • [ 154-23-4 ]
  • 14
  • [ 100-53-8 ]
  • catechin-(4α-8)-epicatechin-(4β-8)-catechin [ No CAS ]
  • [ 20315-25-7 ]
  • [ 37064-35-0 ]
  • [ 72448-81-8 ]
  • [ 115648-76-5 ]
  • [ 154-23-4 ]
  • 16
  • [ 154-23-4 ]
  • [ 480-18-2 ]
  • [ 88314-66-3 ]
  • 17
  • [ 22970-70-3 ]
  • [ 154-23-4 ]
  • [ 20315-25-7 ]
  • [ 12798-59-3 ]
  • [ 23459-99-6 ]
  • 18
  • [ 818-23-5 ]
  • [ 154-23-4 ]
  • catechin 8-pentadecanone ketal [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In tetrahydrofuran at 0℃; 10 min then 10 min;
  • 19
  • [ 462-18-0 ]
  • [ 154-23-4 ]
  • catechin 7-tridecanone ketal [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In tetrahydrofuran at 0℃; 10 min then 10 min;
  • 20
  • [ 86849-67-4 ]
  • [ 154-23-4 ]
  • [ 20315-25-7 ]
  • [ 12798-59-3 ]
  • 21
  • [ 108-24-7 ]
  • [ 154-23-4 ]
  • [ 480-18-2 ]
  • [ 25664-00-0 ]
  • [ 21179-22-6 ]
  • Acetic acid (2R,3S,4S,2'R,3'S)-5,7,3',5',7'-pentaacetoxy-2,2'-bis-(3,4-diacetoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3-yl ester [ No CAS ]
  • 22
  • [ 154-23-4 ]
  • [ 480-18-2 ]
  • [ 51196-37-3 ]
  • 23
  • [ 619-60-3 ]
  • C15H13O6 [ No CAS ]
  • [ 54737-34-7 ]
  • [ 154-23-4 ]
  • 24
  • [ 54737-34-7 ]
  • [ 154-23-4 ]
  • [ 619-60-3 ]
  • C15H13O6 [ No CAS ]
  • 25
  • [ 7228-78-6 ]
  • [ 75-07-0 ]
  • [ 154-23-4 ]
  • 8-{1-[(2S,3R)-2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chroman-8-yl]-ethyl}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromenylium; chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tartaric acid In ethanol
  • 26
  • [ 20315-25-7 ]
  • [ 100-53-8 ]
  • [ 37064-35-0 ]
  • [ 154-23-4 ]
  • 27
  • [ 23459-99-6 ]
  • [ 100-53-8 ]
  • [ 20315-25-7 ]
  • [ 37064-35-0 ]
  • [ 68200-27-1 ]
  • [ 154-23-4 ]
  • 28
  • [ 20315-25-7 ]
  • [ 490-46-0 ]
  • [ 154-23-4 ]
  • 30
  • [ 154-23-4 ]
  • [ 621-54-5 ]
  • [ 31129-94-9 ]
  • (2R)-1-(3-hydroxyphenyl)-3-(2,4,6-triphydroxyphenyl)propan-2-ol [ No CAS ]
  • (2R)-1-(3',4'-dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol [ No CAS ]
  • 31
  • [ 578-86-9 ]
  • [ 154-23-4 ]
  • (2R,4R,2'R,3'S)-2'-(3,4-Dihydroxy-phenyl)-2-(4-hydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-7,3',5',7'-tetraol [ No CAS ]
  • (2S)-7,4'-dihydroxyflavan(4β→8)-catechin [ No CAS ]
  • (2R,4S,2'R,3'S)-2'-(3,4-Dihydroxy-phenyl)-2-(4-hydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-7,3',5',7'-tetraol [ No CAS ]
  • (2S,4S,2'R,3'S)-2'-(3,4-Dihydroxy-phenyl)-2-(4-hydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-7,3',5',7'-tetraol [ No CAS ]
  • 32
  • [ 37064-35-0 ]
  • [ 154-23-4 ]
  • [ 20315-25-7 ]
  • 33
  • [ 37064-35-0 ]
  • [ 154-23-4 ]
  • [ 20315-25-7 ]
  • [ 23459-99-6 ]
  • 34
  • [ 100-39-0 ]
  • [ 154-23-4 ]
  • [ 20728-73-8 ]
YieldReaction ConditionsOperation in experiment
68% EXAMPLE 25 (2R,3R)-2-(3,4-dihydroxyphenyl)-3-methylchroman-3,5,7-triol Step 1 To a stirred solution of 10 (1.0 gm, 3.4 mmol) in DMF, anhydrous K2CO3 (2.3 gm, 17.0 mmol) was added at 0 C. under nitrogen atmosphere. After an additional stirring at this for 15 minutes at same temperature, benzyl bromide (2.0 ml, 17.0 mmol) was added drop-wise. The reaction temperature was allowed to increase upto 25 C. and stiffing was continued for overnight. Consumption of 10 was monitored by TLC. After complete consumption of 10, water (50 ml) was added and organic layer was extracted with ethyl acetate (3*100 ml). The combined organic layers were washed with water, brine and dried over sodium sulphate. The organic layer was concentrated to afford light brown sticky material which was further purified using silica gel column chromatography using 8% ethyl acetate in hexane as eluent to afford 11 as white powder (1.5 gm, 68%). ESIMS: 651 [M++1]
68% To a stirred of [10] (1.0 gm, 3.4 mmol) in DMF was added K2CO3 (2.3 gm, 17.0 mmol) at 0 C. under nitrogen atmosphere. After stirring at this temperature for 15 min, was added Benzyl bromide drop-wise. The temperature of reaction mixture was allowed ,to raise to room temperature and stirred it for overnight. TLC showed complete consumption of [10]. Reaction mixture was quenched with water (50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The organic layer was rotary evaporated to afford light brown sticky material. This crude product was loaded on to silica gel column and eluted with 8% ethyl acetate/hexane to afford white powder [14] (1.5 gm,68%). (0158) Analytical Data: ESIMS: 651[M++1]
68% Step 1: Synthesis Tetrabenzylated Catechin [20] from Catechin [19] To a stirred solution of [19] (1.0 g, 3.4 mmol) in DMF, anhydrous K2CO3 (2.3 g, 17.0 mmol) was added at 0 C. under nitrogen atmosphere. After an additional stirring at this for 15 minutes at same temperature, benzyl bromide (2.0 ml, 17.0 mmol) was added drop-wise. The reaction temperature was allowed to increase up to 25 C. and stirring was continued for overnight. Consumption of [19] was monitored by TLC. After complete consumption of [19], water (50 ml) was added and organic layer was extracted with ethyl acetate (3*100 ml). The combined organic layers were washed with water, brine and dried over sodium sulphate. The organic layer was concentrated to afford light brown sticky material which was further purified using silica gel column chromatography using 8% ethyl acetate in hexane as eluent to afford [20] as white powder (1.5 g, 68%); ESIMS: 651[M++1]
67% With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 26h; To a solution of (+)-<strong>[154-23-4]catechin</strong> (3.02 g, 10.4 mmol) in DMF (38 mL), benzyl bromide (5.57 ml, 46.9 mmol) and K2CO3 (8.63 g, 62.5 mmol) were added at 0 C . The mixture was stirred at 0 C for 2 h and then at room temperature for 24 h. The mixture was diluted with ethyl acetate and was washed successively with water and brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (CH2Cl2 : MeOH= 50 : 1) to give 2. (4.54 g, 67%): 1H NMR (DMSO-d6) delta 7.41 - 7.22 (20H, m), 7.07 (1H, d, J = 1.6 Hz), 7.00 (1H, d, J = 8.4 Hz), 6.86 (1H, d, J = 1.6 and 8.4 Hz), 6.31 (1H, d, J = 2.4 Hz), 6.10 (1H, d, J = 2.4 Hz) , 5.11 - 5.10 (8H,m), 5.03 (1H, d, J = 8.4 Hz), 4.62 (1H, d, J = 7.2 Hz), 3.96 (1H, dddd, J = 5.1, 7.2, 7.8 and 8.4 Hz), 2.74 (1H, dd, J = 5.1 and 16.2 Hz), 2.44 (1H, dd, J = 7.8 and 16.2 Hz).
46% Example 1; Process for Preparing And Purifying of 5,7,3',4'-Tetra-O-benzyl-(+)-<strong>[154-23-4]catechin</strong>; A dry 12 L, three-necked round bottom flask equipped with a mechanical stirrer, a dropping funnel, a nitrogen inlet, and an internal temperature probe was charged with (+)-<strong>[154-23-4]catechin</strong> (400 g, 1.38 moles, 1.0 eq.) and dimethyl formamide (4 L, 1 g/10 mL, 10 eq.). To this was slowly added potassium carbonate (1430.5 g, 10.38 M, 7.5 eq.) with stirring. The suspension was stirred at RT for 30 min. To this was slowly added benzyl bromide (1180.2 g, 6.9 M, 5 eq.) via the addition funnel. A mild exotherm occurred as the internal temperature rose to 30.6 C. from 21.60 C. It took about 4.5 hours to complete the addition of the benzyl bromide. The suspension was stirred at room temperature for 18 to 19 h. The consumption of the starting material was monitored by TLC (30% ethyl acetate:heptane, v/v). The reaction mixture was suction filtered through a pad of celite (500-g) to remove the potassium carbonate. The celite pad was washed four times with ethyl acetate (1 L and three times with ethyl acetate (500 mL each). The combined filtrates were sequentially washed two times with 10% aqueous hydrochloric acid (1.5 L), two times with water (1 L), and one time with 30% aqueous sodium chloride (2 L). The organic layer was dried over anhydrous magnesium sulfate (300 g) and filtered. The solvent was removed under vacuum to afford an off-white to light yellow colored semi-solid. The semi-solid was chased or co-evaporated twice with heptane (500 mL each). The crude product was taken up in trichloroethylene (2 L, 1 g/5 mL based on the (+)-<strong>[154-23-4]catechin</strong> starting material, and heated at reflux until a clear orange to red solution was obtained. The solution was allowed to cool to room temperature with agitation and then it was further cooled to -20 to -26 C. in the freezer for 56 hours. The solids obtained were suction filtered, washed two times with cold trichloroethylene (-20 C., 500 mL) and once with cold heptane (-20 C., 500 mL). The solids were dried under high vacuum at 50-55 C. for 18 hours to produce an off-white to white solid. The yield was 412 g. (46%). The HPLC purity was 97.76% (AUC).
24% A solution of (+)-<strong>[154-23-4]catechin</strong> (65.8 g, 226.7 mmol, anhydrous), dissolved in anhydrous dimethylformamide (DMF, 720 mL), was added dropwise, at room temperature over a period of 80 min, to a stirred suspension of sodium hydride, 60% in oil, (39 g, 975 mmol, 4.3 eq.) in DMF (180 mL). (S. Miura, et al., Radioisotopes, 32, 225-230(1983)). After stirring for 50 min, the flask was placed in a -10 C. NaCl/ice bath. Benzyl bromide (121 mL, 1.02 mol, 4.5 eq.) was added dropwise within 80 min. and the brown reaction mixture warmed to room temperature, with stirring, overnight. The resulting reaction mixture was evaporated and the resulting candy-like solid was dissolved, with heating and stirring, in two portions of solvent each consisting of 200 mL of chloroform (CHCl3) and 100 mL of water. The phases were separated, the aqueous phase extracted with CHCl3 (20 mL), and the combined organic phases washed with water (100 mL), dried over magnesium sulfate (MgSO4) and evaporated. The residue was purified by chromatography on silica gel (42×10 cm; ethyl acetate/chloroform/hexane 1:12:7) to provide, after evaporation and drying in vacuo, 85 g crude product, which was recrystallized from trichloroethylene (1.3 L) to provide 35.1 g (24%) of an off-white powder. 1H NMR (CDCl3) delta7.47-7.25 (m, 20 H), 7.03 (s, 1 H), 6.95 (s, 2 H), 6.27, 6.21 (ABq, 2 H, J=2 Hz), 5.18 (s, 2 H), 5.17 (narrow ABq, 2 H), 5.03 (s, 2 H), 4.99 (s, 2 H), 4.63 (d, 1 H, J=8.5 Hz), 4.00 (m, 1 H), 3.11, 2.65 (ABq, 2 H, J=16.5 Hz, both parts d with J=5.5 and 9 Hz, resp.), 1.59 (d, 1 H, J=3.5 Hz); IR (film) 3440 (br), 1618, 1593, 1513, 1499, 1144, 1116, 733, 696 cm-1; MS m/z 650 (M+, 0.5%),319, 181, 91.

  • 35
  • [ 154-23-4 ]
  • tannin [ No CAS ]
  • [ 20315-25-7 ]
  • [ 12798-59-3 ]
  • 36
  • tannin extract of roots of Fragaria vesca [ No CAS ]
  • [ 29106-49-8 ]
  • [ 20315-25-7 ]
  • [ 12798-57-1 ]
  • [ 154-23-4 ]
  • 37
  • [ 100-53-8 ]
  • rhatannin [ No CAS ]
  • [ 37064-35-0 ]
  • [ 80418-27-5 ]
  • [ 863-03-6 ]
  • [ 154-23-4 ]
  • 38
  • [ 7647-01-0 ]
  • [ 67-56-1 ]
  • [ 528-58-5 ]
  • platinum black [ No CAS ]
  • [ 154-23-4 ]
  • 39
  • [ 2917-26-2 ]
  • epicatechin-4-hexadecylsulphide [ No CAS ]
  • [ 154-23-4 ]
YieldReaction ConditionsOperation in experiment
40% With acetic acid In ethanol at 105℃; for 18h;
  • 40
  • [ 154-23-4 ]
  • [ 3483-12-3 ]
  • (2R,3S)-2-[2-(2,3-Dihydroxy-4-mercapto-butylsulfanyl)-3,4-dihydroxy-phenyl]-chroman-3,5,7-triol [ No CAS ]
  • (2R,3S)-2-[3-(2,3-Dihydroxy-4-mercapto-butylsulfanyl)-4,5-dihydroxy-phenyl]-chroman-3,5,7-triol [ No CAS ]
  • 42
  • [ 20728-73-8 ]
  • [ 154-23-4 ]
YieldReaction ConditionsOperation in experiment
90% With 10 wt% Pd(OH)2 on carbon; In methanol; water; at 20℃; for 10h; O-BzCatechin (11, see the attached Figure) (6,0.1mmol) dissolved in 2 ml of methanol, under the room temperature condition into a chromatogram of pure water (8 ml) and 20% Pd (OH) 2/C (10 mg), stirring the mixture at room temperature for 10 hours, TLC detection reaction is ended. Extraction with ethyl acetate (50mLx3), combined with the phase, drying anhydrous sodium sulfate, filtered, concentrated, column chromatography purification, get Catechin (12, see Figure), the yield is 90%.
  • 43
  • condensed tannin [ No CAS ]
  • [ 490-46-0 ]
  • [ 154-23-4 ]
  • [ 970-73-0 ]
  • [ 970-73-0 ]
  • 44
  • [ 7228-78-6 ]
  • [ 75-07-0 ]
  • [ 154-23-4 ]
  • 8-{1-[(2R,3S)-2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chroman-8-yl]-ethyl}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromenylium; chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid at 25℃; for 48h;
  • 45
  • PZ-5 [ No CAS ]
  • [ 490-61-9 ]
  • [ 154-23-4 ]
  • [ 970-73-0 ]
  • 46
  • [ 141-75-3 ]
  • [ 154-23-4 ]
  • 3-O-butyryl-(+)-catechin [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With trifluoroacetic acid; In tetrahydrofuran; at 20℃; for 17h; (+) -<strong>[154-23-4]catechin</strong> (1. 00g, 3.44 mmol) and butyryl chloride (0.179 ml, 1. 68 mmol) were dissolved in tetrahydrofuran (10 mL) containing trifluoroacetic acid (0.270 ml, 3. 55 mmol), and the solution was stirred for 17 hrs under an Ar gas at room temperature. The reaction mixture was diluted with CHCIs-MeOH (3: 1) and washed five times with water. The organic layer was concentrated in vacuo to give a residue. Purification by the preparative HPLC using a GS-320 column (21.5 mm IDx500 mm) with MeOH as an eluent. , followed by freeze-drying, yielded the desired 3-O-butyryl- (+)-<strong>[154-23-4]catechin</strong> 85 mg as white powder (14.0 % yield). [a] 20D + 7. 8 (EtOH, c= 0.5) ; IR (KBr) 3707,2607, 2326,1697, 1504,1454, 1140, 1013,833, 781, 419 cm-1 ; lH NMR6 : 0.79 (3H, t, J= 7.4 Hz,-COCH2CH2CH3), 1.45-1. 53 (2H, m,-COCH2CH2CH3), 2.13-2. 19 (2H, m,-COCH2CH2CH3), 2.58-2. 62 (1H, m, H-4), 2.78-2. 82 (1H, m, H-4), 5.17-5. 21 (1H, m, H-3), 5.88 (1H, s, H-6 or H-8), 5.93 (1H, s, H-8 or H-6), 6.65-6. 68 (1H, m, H-2'), 6.72 (1H, d, J= 8.0 Hz, H-3'), 6. 78 (1H, s, H-6'); HR- FABMS m/z : 361. 1285 ([M+H] +, Calcd for Cl9H2107 : 361.1287).
  • 47
  • [ 88419-56-1 ]
  • [ 154-23-4 ]
  • 2,4,5-Trifluoro-benzoic acid (2R,3S)-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid In tetrahydrofuran at 20℃; for 24h;
  • 48
  • [ 100-44-7 ]
  • [ 154-23-4 ]
  • [ 20728-73-8 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at -78 - 20℃; for 7.25h;Inert atmosphere; The title compound was prepared by an adaption of the procedure for the same compound reported by Mustafa et al.refPreviewPlaceHolder19CommentTo a stirring solution of (+)-<strong>[154-23-4]catechin</strong> 8 (9.70 g, 33.4 mmol) in DMF (200 mL) at -78 C, NaH (5.7 g, 60% dispersion in mineral oil, 142 mmol, 4.25 equiv) was added as a solid, followed immediately by neat BnCl (20.0 mL, 173 mmol, 5.2 equiv). The resulting mixture was stirred vigorously at -78 C for 15 min, then the cold bath was removed and stirring was continued at room temperature for 7 h. The mixture was poured into EtOAc (400 mL)/water (600 mL) and stirred vigorously for 30 min. The phases were then separated and the organic layer was washed with brine (5×100 mL), then dried (Na2SO4), filtered, and concentrated. The brown residue was purified by filtration over SiO2 (CH2Cl2/hexane 1:1 eluted mineral oil and excess BnCl, then CH2Cl2 eluted product) to provide the tetrabenzyl product (20.5 g, 94%) as a white, crystalline solid after removal of the solvent. The 1H and 13C NMR spectra of the product corresponded to that reported by Mustafa et al. for the title compound 9.refPreviewPlaceHolder19
  • 49
  • [ 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.
  • 50
  • [ 2596-50-1 ]
  • [ 154-23-4 ]
  • LDN-0098009 [ 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 (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%). 170 mg neotheaflavin 3-gallate was obtained. [0094] 1H NMR (CD3OD, 600 MHz): deltaH 8.04 1H s, 7.59 1H s, 7.49 1H s, 6.92 2H s, 6.01 2H d, J=2.4 Hz, 5.98 1H d, J=2.4 Hz, 5.97 1H d, J=2.4 Hz, 5.67 1H brs, 5.56 1H brd, J=6.6 Hz, 5.11 1H s, 4.22 1H m, 3.03 1H dd, J=4.8, 17.4 Hz, 2.92 1H brd, J=16.8 Hz, 2.83 1H dd, J=4.8, 16.8, 2.66 dd, J=8.4, 16.8; 13C NMR (CD3OD, 150 MHz): deltaC 185.8, 167.4, 158.0, 157.9, 157.8, 156.7, 156.5, 155.3, 151.6, 146.9, 146.2, 139.9, 134.0, 132.0, 130.4, 127.7, 122.3, 121.0, 117.6, 110.2, 100.6, 99.2, 96.9, 96.7, 95.9, 95.6, 80.5, 77.1, 69.9, 68.8, 28.5, 27.0 ppm.
  • 51
  • [ 149-91-7 ]
  • [ 154-23-4 ]
  • [ 26258-51-5 ]
  • [ 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; C (0.5 g) and gallic acid (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%). 60 mg theaflavic acid and 20 mg purpurogallin carboxylic acid were obtained. [0106] 1H NMR (CD3OD, 600 MHz): deltaH 9.00 1H s, 7.82 1H s, 7.66 1H s, 5.98 1H d, J=2.4 Hz, 5.91 1H d, J=2.4, 5.43 1H brd, J=7.2 Hz, 4.21 1H, m, 2.94 dd, J=4.8, 16.2 Hz, 2.64 dd, J=4.8, 16.2 Hz; 13C NMR (CD3OD, 150 MHz): deltaC 186.6, 170.3, 157.9, 157.6, 156.6, 154.7, 152.2, 149.3, 139.5, 134.4, 132.2, 128.9, 125.0, 122.7, 116.5, 100.7, 96.8, 96.1, 80.0, 69.1, 29.3 ppm.
  • 52
  • [ 154-23-4 ]
  • [ 970-73-0 ]
  • [ 4670-05-7 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; C (catechin) (0.8 g) and EGC (0.8 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%). 120 mg neotheaflavin was obtained. [0091] 1H NMR ((CD3)2CO, 600 MHz): deltaH 8.26 1H s, 7.46 1H s, 7.63 1H s, 6.06 d, J=2.4 Hz, 6.03 d, J=2.4 Hz, 5.96 d, J=2.4 Hz, 5.95 d, J=2.4 Hz, 5.62 d, J=7.8 Hz, 5.01 1H s, 4.39 1H m, 4.15 1H m, 2.97 dd, J=5.4, 15.6 Hz, 2.91 dd, J=4.2, 16.8, 2.84 dd, J=1.2, 16.8 Hz, 2.66 dd, J=9.6, 15.6 Hz; 13C NMR ((CD3)2CO, 150 MHz): deltaC 184.8, 157.6, 157.5, 157.4, 157.0, 156.7, 156.6, 154.4, 150.5, 146.2, 134.8, 132.2, 130.8, 128.6, 122.3, 121.6, 119.2, 100.7, 99.2, 96.4, 96.3, 95.6, 95.4, 81.5, 79.1, 69.5, 66.6, 30.0, 29.3 ppm.
  • 53
  • [ 123-19-3 ]
  • [ 154-23-4 ]
  • (6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dipropyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran [ No CAS ]
  • 54
  • [ 502-56-7 ]
  • [ 154-23-4 ]
  • (6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dibutyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran [ No CAS ]
  • 55
  • [ 927-49-1 ]
  • [ 154-23-4 ]
  • (6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dipentyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran [ No CAS ]
  • 56
  • [ 462-18-0 ]
  • [ 154-23-4 ]
  • (6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dihexyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran [ No CAS ]
  • 57
  • [ 96-22-0 ]
  • [ 154-23-4 ]
  • (6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-diethyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran [ No CAS ]
  • 58
  • [ 23459-99-6 ]
  • [ 20315-25-7 ]
  • [ 154-23-4 ]
  • 59
  • [ 10083-24-6 ]
  • [ 154-23-4 ]
  • C28H24O9 [ No CAS ]
  • 60
  • [ 154-23-4 ]
  • [ 20315-25-7 ]
  • 61
  • [ 154-23-4 ]
  • [ 480-18-2 ]
YieldReaction ConditionsOperation in experiment
With extract of Burkholderia oxyphila OX-01, Japan, Tsukuba, acidic forest soil; In aq. phosphate buffer; at 28℃; for 3h;pH 7; During preliminary analysis, a reaction mixturecontaining 0.002% (+)-catechin in 50-mM phosphatebuffer (pH 7.0) was prepared. Into 1 mL of thissolution, 25 muL of crude extract solution was addedand the UV spectra of the sample were evaluated at28 C. As control, the same crude extract solution,which was boiled for 15 min to inactivate the enzymesand then centrifuged at 13,000 g for 10 min at 4 C,was employed.
  • 64
  • [ 100-39-0 ]
  • [ 154-23-4 ]
  • tetra-O-benzyl (+)-catechin [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate; In 2,4-dichlorophenoxyacetic acid dimethylamine; Example 1 Preparation of Tetra-O-benzyl-(+)-<strong>[154-23-4]catechin</strong> To a solution of (+)-<strong>[154-23-4]catechin</strong> (580 mg, 2 mmol) in DMA (15 mL), benzyl bromide (960 muL, 4 eq) and K2CO3 (1.7 gm, 6 eq) were added and the mixture stirred at r.t. under argon for 48 hours. The mixture was then partitioned between ethyl acetate and water (50 mL each). The organic layer was washed with water (3*50 mL), then 50 mL saturated NaCl. Removal of the solvent gave a viscous residue from which the title compound was isolated by crystallization from 50 mL methylene chloride:methanol (9:1; v/v) to provide 880 mg of off-white crystals at a yield of 68%. 1H NMR (CDCl3) deltaH 7.44-7.24 (20H, m, Ar-H), 7.0 (1H, s, H-2'), 6.94 (2H, s, H-5', H-6'), 6.25, 6.19 (2*1H, 2*d, J=2.0 Hz, H-6, H-8), 5.16 (4H, s, CH2Ph), 5.0, 4.97 (2*2H, 2*s, CH2Ph), 4.61 (1H, d, J=8.2 Hz, h-2), 3.98 (1H. m, H-3), 3.10 (1H, dd, J=16.5 Hz, H-4alpha), 2.63 (1H, dd, J=8.9, 16.5 Hz, H-4beta).
  • 65
  • [ 154-23-4 ]
  • dehydrodicatechin A [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;tea Kyoken No. 129 variety, leaves; phosphate buffer extract of; In water; at 32℃; for 5h;pH 5.6;Aqueous phosphate buffer; Tea leaves of Kyoken No. 129 variety (supplied from Kyoto Prefectural Tea Research Institute) (100 g) were ground in liquid nitrogen and stirred with 600 ml of an extraction buffer (adjusted to pH 7.0 with 0.01 M KH2PO4 and 0.02 M K2HPO4) and 100 ml of polyamide, and then filtered through gauze. The filtrate was centrifuged at 8000 rpm for 20 min. The supernatant (500 ml) was stirred with 500 ml of acetone precooled to -20C, and then the mixture was allowed to stand at 4C for 1 hr. This solution was centrifuged at 8000 rpm, 4C for 20 min to give a white precipitate. This precipitate was dissolved in 100 ml of a reaction buffer (adjusted to pH 5.6 with 0.01 M citrate and 0.02 M KH2PO4) to prepare an enzymatic solution. To 100 ml of the enzymatic solution were added 100 mg of D-(+)-<strong>[154-23-4]catechin</strong> and 8.8 mM H2O2 and allowed to stand at 32C. After 5 hrs, the reaction was stopped by adding 100 ml of 90% acetonitrile containing 1% TFA. This solution was diluted 1:5 in water and applied onto HP-20 (200 ml, Mitsubishi Kasei Corp.) and washed with water, after which the reaction product was eluted with 400 ml of 90% acetonitrile containing 0.1% TFA and concentrated under reduced pressure, and then lyophilized. The reaction product was purified by preparative HPLC as follows: Column: Develosil C30-UG-5 (20 mm x 250 mm, Nomura Chemical Co., Ltd.)Mobile phase: (A) 0.1% TFA/H2O, (B) 90% CH3CN, 0.1% TFADetection: A280nmFlow rate: 6 ml/minGradient: Linear gradient elution from B20% to B70% for 40 min. This chromatography gave dehydro-di<strong>[154-23-4]catechin</strong> A at an elution time of 21 min (for reference, see FEMS Microbiol. Lett. 143 35-40, 1996).
  • 66
  • [ 20315-25-7 ]
  • [ 60-24-2 ]
  • (-)-4β-(2-hydroxyethylsulfanyl)epicatechin [ No CAS ]
  • [ 154-23-4 ]
  • 67
  • [ 539-88-8 ]
  • [ 154-23-4 ]
  • [ 1198466-41-9 ]
  • 68
  • [ 1694-92-4 ]
  • [ 154-23-4 ]
  • [ 1186527-26-3 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine; In acetonitrile; at -20℃; for 1.5h;Inert atmosphere; General procedure: To a solution of 27 (100 mg, 0.327 mmol) in MeCN (20 ml) were added triethylamine (0.453 ml,3.27 mmol) and 2-nitrobenzenesulfonyl chloride (362 mg, 1.63 mmol) at - 20 C. The mixture was stirred at - 20 C for 1.5 h. The reaction mixture was quenched with 2 M HCl and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by flash column chromatography (CH2Cl2) to afford 28 (377 mg) as a colorless amorphous.
  • 69
  • catechin [ No CAS ]
  • [ 18829-70-4 ]
  • [ 154-23-4 ]
YieldReaction ConditionsOperation in experiment
With sodium dodecyl-sulfate In methanol aq. phosphate buffer; enantioselective reaction;
With chiral β-cyclodextrin column In methanol; water Resolution of racemate; stereospecific reaction;
  • 70
  • [ 6858-46-4 ]
  • [ 154-23-4 ]
  • [ 88197-03-9 ]
  • 71
  • [ 6858-46-4 ]
  • [ 154-23-4 ]
  • [ 105330-52-7 ]
  • [ 105330-51-6 ]
  • 72
  • [ 100-53-8 ]
  • proanthocyanidin [ No CAS ]
  • [ 220886-23-7 ]
  • [ 529-44-2 ]
  • [ 213007-61-5 ]
  • [ 220886-22-6 ]
  • [ 154-23-4 ]
  • [ 2596-50-1 ]
  • (epi)catechin-3-O-gallate benzylthioether [ No CAS ]
  • 73
  • [ 1185733-70-3 ]
  • [ 154-23-4 ]
  • [ 1313434-36-4 ]
YieldReaction ConditionsOperation in experiment
86% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃; for 0.316667h; General procedure: To a solution 35 (0.05 g, 0.17 mmol) in dry DMF (3 mL) was added 1 equiv DBU. Reagent 4 (0.076 g, 0.182 mmol) was added and the mixture was stirred for approximately 3 min. This process was repeated four more times. After the final addition the mixture was stirred for 10 min then diluted with Et2O (30 mL) and washed with 0.1 N HCl, water and satd brine. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc:70% hexane, Rf = 0.5) to give pure 36 as a white foam (0.203 g, 90% yield).
  • 74
  • [ 528-58-5 ]
  • [ 154-23-4 ]
  • [ 35323-91-2 ]
  • 75
  • [ 154-23-4 ]
  • [ 490-46-0 ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 6h;UV-irradiation; General procedure: The solutions of individual catechins were freshly prepared at 575 M with water and ethanolrespectively. Two milliliters of each catechin solution was placed in a 2 mL polypropylene centrifugetube which was exposed to UVB for 6 h with a fully opening lid, and was then stored at -20 C toterminate reactions. The intensity of UVB was achieved at 100 Wcm-2 by placing samples undersix UV lamps (SPECTRONICS BLE-1T158 Tube 15 watt, main output at 312 nm) at a distance of45 cm, which was close to the UVB intensity in the sunlight. All samples were turned back to roomtemperature, and made up to 2 mL prior to HPLC analysis.In a pretest, the potential UVB absorbing effect of polypropylene tube wall on theUVB-induced chemical conversion of catechins (575 M, ethanol) was evaluated by comparing withUVB-transmissive Q-cuvette. The result showed that the photo-induced conversion rates of EC andC in polypropylene tubes slightly decreased by ~8% compared with Q-cuvette, while no significantdifference was observed for other catechins. The polypropylene centrifuge tubes were used in thefollowing studies considering operational convenience and practical use.
  • 76
  • [ 100-44-7 ]
  • [ 154-23-4 ]
  • [ 85443-49-8 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at -78 - 20℃;Inert atmosphere; The title compound was prepared by an adaption of the procedure described above for 5,7,3',4'-tetra-O-benzyl-(+)-<strong>[154-23-4]catechin</strong> (9).CommentNaH (4.67 g, 117 mmol, 60% dispersion in mineral oil, 6 equiv) and BnCl (15.6 mL, 135 mmol, 7 equiv) were added to a solution of (+)-<strong>[154-23-4]catechin</strong> 8 (5.61 g, 19.3 mmol) in DMF (120 mL) at -78 C. The resulting mixture was stirred at -78 C for 15 min, then warmed to room temperature and stirred for a further 24 h. The mixture was then quenched and extracted using the same procedure as for that of 9. Filtration of the residue over SiO2 (CH2Cl2/hexane 1:1 eluted mineral oil and excess BnCl, then CH2Cl2 eluted product) afforded pentabenzyl<strong>[154-23-4]catechin</strong> 4 (13.0 g, 91%) as a white foamy solid after solvent removal. 1H and 13C NMR spectra of the product matched that reported by Kikuchi et al. for the title compound 4.refPreviewPlaceHolder26
  • 77
  • [ 108-73-6 ]
  • [ 154-23-4 ]
  • (1R,2R)-1,3-di(2,4,6-trihydroxyphenyl)-1-(3,4-dihydroxyphenyl)propan-2-ol [ No CAS ]
  • [ 18829-70-4 ]
YieldReaction ConditionsOperation in experiment
1: 16% 2: 10% In methanol for 20h; Irradiation; stereoselective reaction;
  • 78
  • [ 154-23-4 ]
  • [ 35323-91-2 ]
  • [ 490-46-0 ]
YieldReaction ConditionsOperation in experiment
85%; 84% With CHIRAL PAKIC; In ethanol; hexane; at 20℃;Resolution of racemate; The racemic mixture 4 (0.200 g) was dissolved in methanol andseparated on a preparative HPLC using a CHIRAL PAKIC (250×20)mm column at ambient temperature, using hexanes/ethanol (60/40) asthe mobile phase with a flow rate of 18 mL/ minute. (+)-(2S,3S)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol (0.085 g, 85 % yield, 99.6 %ee) eluted first at 4.7 min followed by (-)-(2R,3R)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol (0.084 g, 84 % yield, 99.8 % ee).
With CHIRAL PAK IC (250 X 4.6) mm, 5mu column; In methanol; at 25℃;Resolution of racemate;Product distribution / selectivity; The racemic mixture of epicatechin was dissolved in methanol and checked for its chiral purity on reverse phase CHIRAL PAK IC (250 X 4.6) mm, 5mu column at 25 0 C temperature. The mobile phase used was hexanes/ ethanol/ trifluoroacetic acid// 60/ 40/ 0.05 (v/v/v) with a flow rate of 1.0 ml/minute and sample injection volume of 10 muIota. The signals were monitored at UV 280 nm with PDA. The both isomers separated with a retention time difference of about 1.6 minutes. The faster moving isomer on HPLC eluted at 4.7 minute while the slower moving isomer came at 6.3 minute on a 15 minute run.
With CHIRAL PAK; In methanol; at 25℃;Resolution of racemate; Analytical HPLC Method of Separation: [0213] The racemic mixture of epicatechin was dissolved in methanol and checked for its chiral purity on reverse phase CHIRAL PAK IC (250×4.6) mm, 5mu column at 25 C. temperature. The mobile phase used was hexanes/ethanol/trifluoroacetic acid//60/40/0.05 (v/v/v) with a flow rate of 1.0 ml/minute and sample injection volume of 10 mul. The signals were monitored at UV 280 nm with PDA. The both isomers separated with a retention time difference of about 1.6 minutes. The faster moving isomer on HPLC eluted at 4.7 minute while the slower moving isomer came at 6.3 minute on a 15 minute run Preparative HPLC Method of Separation: [0215] The racemic mixture (0.200 g) was dissolved in methanol and separated on a preparative HPLC on CHIRAL PAK IC (250×20) mm column at 25 C. temperature. The sample injection volume was 2.0 ml with a feed concentration of 5 mg/ml. The mobile phase used was Hexanes/EtOH//60/40 v/v with a flow rate of 18 ml/minute. The detection was done at UV 280 nm with PDA. The faster moving epicatechin isomer I (0.085 g) eluted at 4.7 minute and the slower moving epicatechin isomer II (0.084 g) at 6.3 minute with a qualitative purity of 99.6% and 99.8% respectively. Assignment of absolute configuration to the either of the resolved isomers was done based on retention time of the two enantiomers of the racemic epicatechin synthesized compared with the retention time of the commercially available natural epicatechin (2R,3R) under similar HPLC conditions. Based on the retention time, the slow moving isomer eluted at 6.3 minutes was assigned to be (-)-epicatechin ((2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol)isomer and the fast moving isomer which eluted at 4.7 minutes was assigned to be (+)-epicatechin (((2S,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol)isomer.
  • 79
  • [ 7228-78-6 ]
  • [ 154-23-4 ]
  • [ 1399679-45-8 ]
YieldReaction ConditionsOperation in experiment
In water at 50℃; for 168h; Darkness;
  • 80
  • [ 154-23-4 ]
  • C15H7(2)H7O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water-d2; ammonium formate; In aq. buffer; at 60℃; for 72h;pH 3.0;Darkness; General procedure: In general, methanolic stocks (1 mg/ml) of each standard compound were prepared in 2.0-ml microcentrifuge tubes. From these stocks, aliquots were transferred to 1.5-ml microcentrifuge tubesand concentrated to dryness via vacuum centrifugation. The resulting pellets were reconstituted in deuterated methanol (10% of finalvolume) and diluted to volume with MACD labeling buffer (D2Ocontaining 10 mM ammonium formate, pH 3.0). The samples were then incubated in the dark for 72 h at 60 C and then frozen at20 C to stop the labeling reaction. Labeling controls were also generated by reacting each compound in nondeuterated buffer(H2O containing 10 mM ammonium formate, pH 3.0). In addition to these standard conditions, various MACD labeling buffers as wellas reaction times and temperatures were also evaluated in the time course of atom % incorporation and compound degradation studies described below (see Fig. 3). Except for the analysis of quercetinand <strong>[154-23-4]catechin</strong> in Figs. 1 and 2 (see figures below in Results and Discussion),respectively, all reactions were conducted in triplicateand analyzed independently.
  • 81
  • [ 112-16-3 ]
  • [ 154-23-4 ]
  • 3',4',3,5,7-pentadodecanoyl (+)-catechin [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With pyridine; dmap; at 20℃; for 24h; To a solution of (+)-<strong>[154-23-4]catechin</strong> (435.5 mg, 1.50 mmol) in THF(25 ml) was added pyridine (2.42 ml, 30.0 mmol) and DMAP(9.6 mg, 0.075 mmol), and then dodecanoyl chloride (5.20 ml,22.5 mmol) was dripped into the stirred mixture. The reaction was allowed to stand at ambient temperature for 24 h (Raabet al., 2010). Then the reaction mixture was extracted with ethylacetate, dried over MgSO4 and concentrated under reduced pressure.Flash chromatography (SiO2; elution:hexanes/ethyl acetate,10:1) was applied to obtain the fully acylated product as a light yellow powder.
  • 82
  • [ 110-87-2 ]
  • [ 154-23-4 ]
  • C20H22O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With toluene-4-sulfonic acid; In tetrahydrofuran; at 20℃; for 0.666667h; To a solution of (+)-<strong>[154-23-4]catechin</strong> (639.0 mg, 2.20 mmol) in THF (33 ml) was added p-toluenesulfonic acid (84.0 mg, 0.44 mmol)and dihydropyran (602.0 ll, 6.60 mmol) After stirring for 40 min at ambient temperature,the reaction mixture was extracted with EtOAc, washed with water and dried over MgSO4. The afforded syrup after evaporation was subjected to flash chromatography purification (SiO2; elution:chloroform/methanol, 20:1) to give the product a1 as a light yellowsolid (418.8 mg).
  • 83
  • [ 753-73-1 ]
  • [ 154-23-4 ]
  • C15H12Cl2O6Sn [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In tetrahydrofuran; at 20℃; for 0.333333h; <strong>[154-23-4](+)-Catechin</strong> (145.7 mg, 0.5 mmol) was dissolved in THF(7.5 ml), followed by sequential addition of NaHCO3 (84.6 mg,1.0 mmol) and dimethyltin dichloride (Me2SnCl2) (132.3 mg,0.6 mmol). After the solution was stirred at ambient temperaturefor 20 min, dodecanoyl chloride (173.6 ll, 0.75 mmol) was slowlydripped into the mixture. Then the reaction was terminated after 7 h. The crude product afforded by aqueous work-up and EtOAc extraction was purified by chromatography(SiO2; elution:chloroform/methanol, 15:1) and providedthe mixture of compound 2 and 3 as light yellow power.
  • 84
  • [ 154-23-4 ]
  • [ 35323-91-2 ]
  • [ 490-46-0 ]
YieldReaction ConditionsOperation in experiment
0.085 g; 0.084 g With CHIRAL PAK IC; In methanol; ethanol; hexane; at 25℃;Resolution of racemate; The racemic mixture (0.200 g) was dissolved in methanol and separated on a preparative HPLC on CHIRAL PAK IC (250×20) mm column at 25 C. temperature. The sample injection volume was 2.0 ml with a feed concentration of 5 mg/ml. The mobile phase used was Hexanes/EtOH//60/40 v/v with a flow rate of 18 ml/minute. The detection was done at UV 280 nm with PDA. The faster moving (+)Epicatechin isomer I (0.085 g; Chiral purity by HPLC >99%) eluted at 4.7 minute and the slower moving (-) Epicatechin isomer II (0.084 g; Chiral Purity by HPLC >99%) at 6.3 minute.
  • 85
  • C50H42O6 [ No CAS ]
  • [ 490-46-0 ]
  • [ 154-23-4 ]
YieldReaction ConditionsOperation in experiment
55% With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20 - 55℃; TO a stirred solution of [13] (0.180 gm, 0.24 mmol) in 1:1 mixture ethyl acetate and methanol (8 ml), was added a slurry of 10% Pd/C (0.020 gm) at room temperature. The reaction mixture was stirred at this temperature for 1 hr and then reaction temperature was raised to 50 C.-55 C. and stirred at this temperature for overnight. The reaction mass was filtered over celite and the solvent was removed under rotary evaporator to afford light brown sticky material. This crude product was loaded on to silica gel column and eluted with 4% methanol/Dichloromethane to afford off white powder [9](0.04 gm,55%) along with some catechin . (0170) Analytical Data: ESIMS: 291[M++1]
Same Skeleton Products
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