Hydrochloric Acid → Resveratrol

HRID 278829

Reaction equation

HRID 278829 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]2[CH:14]=[C:13]([O:15][C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[CH:12]=[C:11]([OH:27])[CH:10]=2)=[CH:5][CH:4]=[C:3]([OH:28])[CH:2]=1.Cl>O>[C:9]1(/[CH:8]=[CH:7]/[C:6]2[CH:5]=[CH:4][C:3]([OH:28])=[CH:2][CH:1]=2)[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]([OH:27])[CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 5281718Polydatin

Product 1

HCID 445154ResveratrolYield 97,491.898%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The following example illustrates conversion of a β-D-glycosylated stilbene to the aglycone. 200 mg of 90% trans-piceid (3,4′5-trans-trihydroxystilbene -3-β-mono-D-glucoside, BZ1-69-1) was mixed with 5 ml of concentrated hydrochloric acid and 95 ml water (5% HCl v/v) and refluxed with agitation at 100° C. for 90 minutes to yield 114 g (57% yield) trans-resveratrol (trans-3,4′,5-trihydroxystilbene).

Sources & evidence

ORD record
ord-ceee14f390a041b695a415d57ac7161c
Source dataset
uspto-grants-2002_03
Patent number
US06361815B1

Linked notes

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