Hydrochloric Acid → Limonin

HRID 874085Notes

Reaction equation

HRID 874085 reaction equation
[CH3:1][C@:2]12[C@H:13]([C:14]3[CH:15]=[CH:16][O:17][CH:18]=3)[O:12][C:10](=[O:11])[C@H:8]3[O:9][C@@:7]13[C@:6]1([CH3:34])[C:19]([CH2:21][C@H:22]3[C:31]([CH3:33])([CH3:32])[O:30][C@@H:29]4[C@:23]3([CH2:24][O:25][C:26]([CH2:28]4)=[O:27])[C@H:5]1[CH2:4][CH2:3]2)=[O:20].C[C@@]12[C@@H](O)CC[C@H]1[C@@H]1CCC3C=C(O)C=CC=3[C@H]1CC2.C(O)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O.Cl>>[CH3:1][C@:2]12[C@H:13]([C:14]3[CH:15]=[CH:16][O:17][CH:18]=3)[O:12][C:10](=[O:11])[C@H:8]3[O:9][C@@:7]13[C@:6]1([CH3:34])[C:19]([CH2:21][C@H:22]3[C:31]([CH3:33])([CH3:32])[O:30][C@@H:29]4[C@:23]3([CH2:24][O:25][C:26]([CH2:28]4)=[O:27])[C@H:5]1[CH2:4][CH2:3]2)=[O:20]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131732574HCID 131732574, compound

Product 1

HCID 179651Limonin

Conditions

Temperature
30 °C

Procedure

In particular, aqueous solutions of limonin-17-β-D-glucopyranoside (0.35 mg/L) adjusted to pH value of 2.0, 3.0, and 3.5, respectively, by adding trace amounts of hydrochloric acid (1 mol/L) were maintained at different temperatures (4, 20, 30° C.) for up to 14 weeks in closed vials in the dark. At regular time intervals, samples (5 μL) were withdrawn with a syringe and were analyzed for the generation of limonin by means of LC-MS/MS on a Synergi Fusion, 150×2 mm i.d., 4 μm column (Phenomenex). To achieve this, chromatography was performed with a flow rate of 250 μL/min starting with a mixture (80/20, v/v) of 0.1% aqueous formic acid and acetonitrile, increasing the acetonitrile content to 40% within 10 min, then to 80% within 5 min, held for 5 min, and, finally, to 100% within 5 min. Using negative electrospray ionization, limonin was analyzed in the multiple reaction monitoring (MRM) mode using the mass transition m/z 469→229. Quantitative analysis was performed by comparing the peak areas obtained for the mass trace with those of defined standard solutions of limonin in methanol.

Workup

  1. customAt regular time intervals, samples (5 μL) were withdrawn with a syringe
  2. temperaturev/v) of 0.1% aqueous formic acid and acetonitrile, increasing the acetonitrile content to 40% within 10 min
  3. waitheld for 5 min
  4. waitfinally, to 100% within 5 min

Sources & evidence

ORD record
ord-41f5f77c71d649eab34845857cf7e465
Source dataset
uspto-grants-2015_03
Patent number
US08980352B2

Reaction notes

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