Ethyl Acetate → Beta-D-Glucose

HRID 222519

Reaction equation

HRID 222519 reaction equation
[CH:1]1(C2(C3C=CC(OC)=C(OC)C=3)CC(=O)C3C(=CC(O)=CC=3)O2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C(OCC)(=[O:36])C>CO>[OH:36][C@@H:1]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 68553782HCID 68553782, compound

Product 1

HCID 64689Beta-D-Glucose

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound (3), was obtained as a pale yellow crystalline mass from (ethyl acetate:methanol; 9:1) eluants. It responded to positive tests of flavonoid glycosides. Its IR spectrum showed characteristic absorption suggested that a flavanone was an aglycone moiety possessing one hydroxyl group in ring A and two methoxy groups in ring B. Further analysis indicated that (3) was an acyclic sesquiterpenic acid possessing three vinylic linkages at carbons C3″, C7″ (14″) and C-10″ was esterified with the sugar moiety. The 1H NMR spectrum of (3) exhibited the presence of aromatic carbons and sugar carbons. Acid hydrolysis of (3) yielded β-D-glucose as a glycone moiety (TLC comparable). On the basis spectral data analysis of (3), the structure has been established as 6″-(3′″,11′″-dimethyl-dodec-3′″,7′″(14′″) 10′″-trienyl glucopyranosyl-7-hydroxy-3′,4′-dimethoxyflavanone.

Workup

  1. customabsorption
  2. customAcid hydrolysis of (3)

Sources & evidence

ORD record
ord-b2576965ff3f47069e4677cbbd2c391a
Source dataset
uspto-grants-2012_06
Patent number
US08207313B2

Linked notes

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