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CAS No. : | 480-18-2 | MDL No. : | MFCD15146487 |
Formula : | C15H12O7 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CXQWRCVTCMQVQX-LSDHHAIUSA-N |
M.W : | 304.25 | Pubchem ID : | 439533 |
Synonyms : |
(+)-Dihydroquercetin;Dihydroquercetin;Catechin hydrate;Lavitol;Lariksin;Taxifoliol;(+)-Taxifolin
|
Chemical Name : | (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one |
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.13 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 5.0 |
Molar Refractivity : | 74.76 |
TPSA : | 127.45 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.48 cm/s |
Log Po/w (iLOGP) : | 0.71 |
Log Po/w (XLOGP3) : | 0.95 |
Log Po/w (WLOGP) : | 0.86 |
Log Po/w (MLOGP) : | -0.64 |
Log Po/w (SILICOS-IT) : | 0.66 |
Consensus Log Po/w : | 0.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.66 |
Solubility : | 0.662 mg/ml ; 0.00218 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.21 |
Solubility : | 0.186 mg/ml ; 0.000612 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.03 |
Solubility : | 2.87 mg/ml ; 0.00942 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.51 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Catechin-(4alpha ? 2)-phloroglucinol was prepared from (+)-<strong>[480-18-2]taxifolin</strong> according to the method of Kennedy and Jones (2001). Briefly, (+)-<strong>[480-18-2]taxifolin</strong> (51.2 mg) and NaBH4 (24.5 mg) were stirred in absolute EtOH (10 mL) at room temperature for 1 h. Phloroglucinol (175.5 mg) was dissolved in 0.1 N HCl (10 mL) and then combined with the reaction mixture and stirred for 30 min, followed by addition of 10 mL H2O and extraction with EtOAc (3 × 10 mL). The extract was lyophilized to dry powder. The production of the desired compound was confirmed by LC-ESI-TOFMS analysis. The retention time of epicatechin-(4beta ? 2)-phloroglucinol was confirmed by phloroglucinol degradation of procyanidin B2, which had been previously isolated. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NADPH; In aq. buffer; at 45℃; for 0.5h;pH 6;Enzymatic reaction; | General procedure: Enzymatic assay was carried out to examine the catalytic activity of the recombinant VbDFRin a 500 L reaction volume in a 1.5 mL tube. Two commercially available metabolites, <strong>[480-18-2]taxifolin</strong>(dihydroquercetin, DHQ) and ()-dihydrokaempferol (DHK), were used as substrates. NADPH wasused as co-enzyme. Each reaction was composed of 50 mM pH 6 citrate buffer, 20 g NADPH, 15 gsubstrates, and 50 g purified recombinant VbDFR. The reaction time and temperature were 30 minand 45 C. The reaction was stopped by addition of 1.0 mL ethyl acetate (EA) and vigorously vortexed.After centrifugation at 10,000 rpm 2 min, the upper EA phase was transferred into a new tube andevaporated in a speedy vacuum at room temperature. The remaining residue was dissolved in 50 Lmethanol for HPLC analysis.HPLC analysis of VbDFR products was performed on a Shimadzu LC-20AT instrument equippedwith an SPD-M20A photodiode array detector (Shimadzu, Japan). Metabolites were separated witha diamonsil C18 reversed phase column and detected at 280 nm. The elution solvent system consistedof 1% phosphate (solvent A) and methanol (solvent B). For <strong>[480-18-2]taxifolin</strong> assay, a linear gradient programwas developed to elute metabolites, which was composed of three gradient ratios of B:A, 0-8 min:solvent B from 15% to 60%, 9-15 min: solvent B from 60-15%, and 16-25 min: 15% solvent B at a flowrate 1.5 mL/min. For DHK assay, a different linear gradient program was developed for metaboliteseparation, which was composed of three gradient ratios of B:A, 0-20 min: solvent B from 15-60%,21-28 min: solvent B from 60-15%, and 29-35 min: solvent B 15% at a flow rate of 1 mL/min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
dextransucrase; In water; dimethyl sulfoxide; at 30℃; for 22h;pH 5.2;Sodium acetate buffer; Calcium chloride; Enzymatic reaction;Product distribution / selectivity; | Example 1Synthesis of Glucosylated Taxifolin; Solubility in Water of Highly Purified Glucosylated Taxifolin and Stability of the Glucosylated Derivative Molecule at Temperatures Ranging from 4 C. to 45 C.The conditions that were carried out for the synthesis of glucosylated Taxifolin are as follows (amounts for 1 liter of reaction medium): Ingredient Origin Amount Concentration Solution of Taxifolin at Taxifolin: SIGMA T 4512 100 ml Taxifolin: 9 g/L 90 g/L in pure DMSO DMSO Riedel de Haen 60153 250 ml Total DMSO: 350 ml/L Sodium acetate buffer Acetic acid: 40 ml Sodium acetate: 500 mM pH 5.2 Prolabo 20104.298 20 mM Sodium hydroxide: Riedel de Haen 6203 Sucrose at 500 g/L Prolabo 27478.296 300 ml 150 g/L (1,462 M) 0.439 M Water Deionized Qsp 1.00 L No. Calcium chloride, Merck 1.02382.0500 10 mg 10 mg/L dihydrate (can also be introduced in the reaction medium in the form of a solution at 2 g/L; the dose is then 5 ml/L) DextransucrasePurified from L. mesenteroides 170 ml 3.1 U/ml preparation (18 U/ml) NRRL B- 512F culture broth The reaction medium without the enzyme was first obtained by mixing the various solutions in the order reported in the table. The mixture was incubated at 30 C. during a period of time sufficient to attain the desired temperature of 30 C. (plus or minus 0.2 C.). Then the reaction was started by introducing the enzyme preparation. The reaction medium may be moderately agitated.The enzyme preparation has been obtained as follows: the culture broth of Leuconostoc mesenteroides NRRL B512-F titrating an enzyme activity ranging from 4 to 6 U/ml is centrifuged in order to completely separate the microbial cells from the liquid containing the enzyme. The centrifugation supernatant was then concentrated 4 to 10 times by tangential ultrafiltration (molecular weight cut off of 100 kDa). The retentate was then diluted 4 times with 20 mM acetate buffer pH 5.2 containing calcium chloride dihydrate at 10 mg/L and then concentrated 4 times in order to extensively remove the residual low molecular weight components of the cell culture medium containing the enzyme. The purified enzyme preparation has then been stored in a freezed form (-20 C.) or freeze dried up to several months without loss of activity. As a general procedure, the activity of the enzyme preparation is adjusted by intensifying the concentration of the retentate in order that the volume of the enzyme preparation will not be higher than 20% of the final volume of the synthesis reaction medium.The reaction medium was incubated at 30 C. (plus or minus 0.2 C.) during 22 hours. An aliquote of the reaction medium was taken off from the reaction medium and diluted 50 times with a solution containing methanol and water in the proportions of 40/60. The methanolic solution was then analyzed by HPLC.The analysis conditions were those as previously described excepted that the profile of the methanol concentration was as follows (Method 2): solvent A: deionized water containing 1% v/v acetic acid solvent B: HPLC grade methanol containing 1% v/v acetic acid 0 to 10 minutes: 60% A; 40% B; 1 ml/minute 10 to 12 minutes: 60% to 20% A (linear); 40% to 80% B (linear); 1 ml/minute 12 to 14 minutes: 20% A; 80% B; 1 ml/minute 14 to 16 minutes: 20% to 60% A (linear); 80% to 40% B (linear); 1 ml/minute 16 to 25 minutes: 60% A; 40% B; 1 ml/minute 25 minutes: next injection FIG. 7 shows the HPLC chromatogram of the reaction medium containing Taxifolin as glucoside acceptor (289 nm) at just the beginning of the incubation. The major pic at 8.15 minutes corresponds to Taxifolin.FIG. 8 shows the HPLC chromatogram of the reaction medium containing Taxifolin as glucoside acceptor (289 nm) after 22 hours of incubation. A pic with a retention time of 6.15 minutes is observed.FIG. 9 shows the mass spectrum and FIG. 10 the UV spectrum of the pic eluted at around 8.15 minutes: the substance is Taxifolin (m/z [M-H]: 302.96 and m/z [M-H-H2O]: 284.96) which molecular weight is 304.FIG. 11 shows the mass spectrum and FIG. 12 the UV spectrum of the pic eluted at around 6.15 minutes: the corresponding substance is Taxifolin glucoside (m/z [M-H]: 464.98) since its molecular weight is 466.The substances eluted at 9.33 and 12.75 minutes are polyphenolic substances found in the Taxifolin preparation.FIG. 13 shows a the HPLC chromatogram of an aqueous solution containing Taxifolin and Taxifolin glucoside after carrying out purification to remove the enzyme, dextran, fructose and DMSO and a fraction of residual Taxifolin. The eluting conditions are those previously described in which the initial content of methanol is 10% (method 1). Taxifolin is eluted at 24.01 minutes and Taxifolin glucoside at 22.33 minutes.Taxifolin glucoside has been purified extensively to reduce as much as possible the Taxifolin concentration. It was finally obtained a solution titrating more than 93 mM of Taxifolin glucoside with a Taxifolin residual concentration of less than 2 mM (FIG. 14; Taxifolin eluted at... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water;Saccharomyces cerevisiae alpha-glucosidase; at 30℃; for 18h;pH 7.3;Enzymatic reaction; Potassium phosphate buffer; | Example 4Activation of Taxifolin Glucoside by an alpha-Glucosidase PreparationTaxifolin glucoside was incubated in the presence of an alpha-glucosidase enzyme in the following conditions: Taxifolin glucoside obtained as described in example 1 (highly purified preparation corresponding to the HPLC chromatogram reported in FIG. 14): 0.25 ml; alpha-glucosidase (from Saccharomyces cerevisiae; FLUKA 70797; lot 0641337/1; activity: 5.8 U/mg): 50.1 mg in 5 ml of potassium phosphate buffer 0.1 M, pH 7.3; no enzyme in the control reaction medium; Temperature: 30 C.; Moderate agitation. The reaction media were analysed by HPLC (method 2) after a 2-fold dilution of an aliquote with methanol.After 18 hours of incubation, the Taxifolin glucoside molecule remained unchanged in the medium which did not contain the alpha-glucosidase enzyme whereas the Taxifolin glucoside molecule was totally converted into Taxifolin in the presence of the alpha-glucosidase enzyme.These results show that an isolated enzyme specific for the hydrolysis of alpha-glucosidic bonds is able to hydrolyse the Taxifolin glucoside molecule: this indicates that the Taxifolin glucoside molecule contains Taxifolin and glucose with glucose being linked to an hydroxyl group of Taxifolin through an alpha-glucosidic bond. For this reason, the synthesized new glucoside derivatives are claimed O-alpha-D-glucoside derivatives. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In 1,4-dioxane; at 100℃; for 1h; | General procedure: Sugar identification was conducted according to a previously reported procedure (Luecha et al., 2009). Compound 1 (2 mg) was heated to 100 C with dioxane (0.05 mL) and 5% H2SO4 (0.05 mL) for 1 h. After dilution with H2O, the reaction mixture was extracted twice with EtOAc. The EtOAc layer was evaporated to give (+)-taxifolin (18) as an amorphous solid, and 18 was identified by direct comparison with an authentic sample. The aqueous layer was passed through an Amberlite IRA-60E column. The H2O eluate was then concentrated, and the residue was treated with d-cysteine (0.05 mg) in H2O (0.03 mL) and pyridine (0.015 mL) at 60 C for 1 h with stirring. After the solution had been concentrated and the reaction mixture dried, pyridine (0.015 mL), hexamethyldisilazane (0.015 mL), and trimethylsilyl chloride (0.015 mL) were added to the residue. The reaction mixture was then heated at 60 C for 30 min, and the supernatant was analyzed by GC. GC conditions: column GL Sciences TC-l, 0.25 mm x 30 m; column temp: 235 C; carrier gas: N2; tR (min): D-rhamnose (11.4), L-rhamnose (11.6). The tR of l-rhamnose was detected from 1. Acid hydrolysis of other compounds was performed in the same manner as used for 1, and the tR of L-rhamnose was detected in these compounds. |
Tags: 480-18-2 synthesis path| 480-18-2 SDS| 480-18-2 COA| 480-18-2 purity| 480-18-2 application| 480-18-2 NMR| 480-18-2 COA| 480-18-2 structure
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