Hydrochloric Acid → Retinoyl beta-glucuronide

HRID 1461417

Reaktionsgleichung

Reaktionsgleichung von HRID 1461417
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18](F)=[O:19].[O:23]=[CH:24][C@@H:25]([C@H:27]([C@@H:29]([C@@H:31]([C:33]([OH:35])=[O:34])[OH:32])[OH:30])[OH:28])[OH:26].C(=O)(O)[O-].[Na+].Cl>CC(C)=O.O>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18]([O:23][C@@H:24]1[O:32][C@H:31]([C:33]([OH:35])=[O:34])[C@@H:29]([OH:30])[C@H:27]([OH:28])[C@H:25]1[OH:26])=[O:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 65041Glucuronic AcidHCID 516892Sodium BicarbonateHCID 5378594(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl fluoride2×

Produkt 1

HCID 5281877Retinoyl beta-glucuronideAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

Retinoyl fluoride (2.4 g, 7.9 mmol) was dissolved in 200 ml of acetone. D-glucuronic acid (6 g, 31 mmol) dissolved in 50 ml of water and sodium bicarbonate (970 mg) dissolved in 50 ml of water were added to the retinoyl fluoride solution. The mixture wa stirred at room temperature for 20-24 hrs. The solution was neutralized with lN HCl, diluted with water, and the product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and then evaporated to dryness in a rotary evaporator. The residue was dissolved in 2-3 ml of diethyl ether and transferred to a silica gel (for dry column chromatography, wet packed with hexane) column. The column was developed with hexane containing diethyl ether (5-50%) to remove retinoic acid and other products. The major yellow band containing retinoyl glucuronide was next eluted with a mixture of CH2Cl2 /CH3OH (1:1). The solvent was evaporated to dryness to give solid retinoyl β-glucuronide (2.3 g, 60%). This preparation consisted mainly of the all-trans isomer, and can be used as such.

Aufarbeitung

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness in a rotary evaporator
  5. dissolutionThe residue was dissolved in 2-3 ml of diethyl ether
  6. additioncontaining diethyl ether (5-50%)
  7. customto remove retinoic acid and other products
  8. additionThe major yellow band containing retinoyl glucuronide
  9. washwas next eluted with a mixture of CH2Cl2 /CH3OH (1:1)
  10. customThe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-747ceb3287814642b02f6d2c67881f56
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075340

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