3,5,7,3',4'-Pentahydroxyflavanone → Vanillin

HRID 1394571

Reaction equation

HRID 1394571 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH3:12][N:13]([C:15](=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:16]=[O:17])[CH3:14].[CH:25]1[C:30]([CH:31]2[O:41][C:40]3[CH:39]=[C:38]([OH:42])[CH:37]=[C:36]([OH:43])[C:35]=3[C:33](=O)[CH:32]2[OH:44])=[CH:29][C:28]([OH:45])=[C:27]([OH:46])[CH:26]=1>Cl.CO>[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH3:12][N:13]([C:15](=[CH:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:16]=[O:17])[CH3:14].[CH:25]1[C:30]([CH:31]2[O:41][C:40]3[CH:39]=[C:38]([OH:42])[CH:37]=[C:36]([OH:43])[C:35]=3[CH2:33][CH:32]2[OH:44])=[CH:29][C:28]([OH:45])=[C:27]([OH:46])[CH:26]=1

Participants

8

Reactant 3

HCID 4713,5,7,3',4'-PentahydroxyflavanoneHCID 1183VanillinHCID 54119736HCID 54119736, compound

Product 3

HCID 1183VanillinYield 1%HCID 12032-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triolHCID 54119736HCID 54119736, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Working solution of 1% vanillin was prepared by dissolving 0.1 g of vanillin in 10 mL of 5 N HCl, whereas 5% dimethylaminocinnamaldehyde (DMACA) was prepared in methanol containing 5% H2SO4. Lyophilized extract for 100 mg of dry kernels was dissolved in 0.5 mL of vanillin or DMACA working solutions. Taxifolin and catechin each at a concentration of 100 ppm were used as reference compounds for color reactions. Because vanillin is catechin-specific and produces bright red color, no color is developed when it reacts with taxifolin. DMACA reacting with catechin produces dark greenish blue color, whereas reacting with taxifolin produces purple color.

Workup

  1. extractionLyophilized extract for 100 mg of dry kernels
  2. dissolutionwas dissolved in 0.5 mL of vanillin
  3. customproduces bright red color

Sources & evidence

ORD record
ord-1f667d9385214a6a8ee33448a7929562
Source dataset
uspto-grants-2008_03
Patent number
US07348475B2

Linked notes

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