Daidzin → Isoflavone

HRID 227207

Reaction equation

HRID 227207 reaction equation
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[CH:14]=[CH:13][C:12](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3](O)[CH:2]=1.C1C(C2C(=O)C3C(O)=CC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=CC=3OC=2)=CC=C(O)C=1.COC1C=C2C(C(C3C=CC(O)=CC=3)=COC2=CC=1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=O.C1C(C2C(=O)C3C=CC(O)=CC=3OC=2)=CC=C(O)C=1.C1C(C2C(=O)C3C(O)=CC(O)=CC=3OC=2)=CC=C(O)C=1.COC1C=C2C(=O)C(C3C=CC(O)=CC=3)=COC2=CC=1O.C1C(C2C(=O)C3C=CC(O[C@@H]4O[C@H](COC(CC(O)=O)=O)[C@@H](O)[C@H](O)[C@H]4O)=CC=3OC=2)=CC=C(O)C=1.C1C(C2C(=O)C3C(=CC(O[C@@H]4O[C@H](COC(CC(O)=O)=O)[C@@H](O)[C@H](O)[C@H]4O)=CC=3O)OC=2)=CC=C(O)C=1.COC1C=C2C(C(C3C=CC(O)=CC=3)=COC2=CC=1O[C@@H]1O[C@H](COC(CC(O)=O)=O)[C@@H](O)[C@H](O)[C@H]1O)=O.COC[C@H]1O[C@@H](OC2C=CC3C(C(C4C=CC(O)=CC=4)=COC=3C=2)=O)[C@H](O)[C@@H](O)[C@@H]1O.CC(OC[C@H]1O[C@@H](OC2C=C3OC=C(C4C=CC(O)=CC=4)C(=O)C3=CC=2OC)[C@H](O)[C@@H](O)[C@@H]1O)=O>C(O)C>[O:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[O:17])[C:7]([C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=2)=[CH:8]1

Participants

13

Reactant 11

HCID 107971Daidzin3×HCID 187808GlycitinHCID 5280961GenisteinHCID 5281377GenistinHCID 5281708DaidzeinHCID 5317750GlyciteinHCID 99139686''-O-MalonyldaidzinHCID 102280956''-O-AcetylglycitinHCID 15934091MalonylgenistinHCID 237246576''-O-MalonylglycitinHCID 102028680Acetyl daidzin

Product 1

HCID 72304Isoflavone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sample corresponding to 1 to 10 mg of isoflavones was precisely weighed, and 25 mL of 70% (v/v) ethanol was added to the sample. After extraction with stirring for 30 minutes at room temperature, the extract was centrifuged. The residue was further extracted twice in the same way as in the above. Extract solutions from three extractions in total were combined, adjusted to a volume of 100 mL with 70% (v/v) ethanol, and then filtered with a 0.45 μm PVDF filter to obtain a test solution. In a confirmatory test of isoflavones, the peaks of the test solution were confirmed at about the same retention times as compared with 12 kinds of standard samples, namely, daidzin, genistin, glycitin, daidzein, genistein, glycitein, malonyl daidzin, malonyl genistin, malonyl glycitin, acetyl daidzin, acetyl genistin and acetyl glycitin (all manufactured by Waco Pure Chemical Industries, Inc.). In a quantitative test, the concentrations of 12 isoflavones in the test solution were quantified (as equivalent converted into daidzin) using daidzin standard samples as standard. The true isoflavone concentrations were calculated by multiplying the obtained values by the following quantification constants: daidzin (1.000), genistin (0.814), glycitin (1.090), malonyl daidzin (1.444), malonyl genistin (1.095), malonyl glycitin (1.351), acetyl daidzin (1.094), acetyl genistin (1.064), acetyl glycitin (1.197), daidzein (0.583), genistein (0.528), and glycitein (0.740). The total amount of isoflavones was determined from the sum of the concentrations of all isoflavones. HPLC conditions of the test solutions and the standard solutions are shown in Table 1.

Workup

  1. extractionAfter extraction
  2. extractionThe residue was further extracted twice in the same way as in the above
  3. extractionExtract solutions from three extractions in total
  4. filtrationfiltered with a 0.45 μm PVDF
  5. filtrationfilter
  6. customto obtain a test solution
  7. concentrationThe true isoflavone concentrations

Sources & evidence

ORD record
ord-b0fc053379584af48c5d0f22b5057a5f
Source dataset
uspto-grants-2009_07
Patent number
US07560131B2

Linked notes

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