Water → Retinoyl beta-glucuronide

HRID 1722491

反応式

HRID 1722491 の反応式
[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].O.C(=O)(O)[O-].[Na+]>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]

参加物

6

反応物 4

HCID 962Water2 回HCID 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 fluoride

生成物 1

HCID 5281877Retinoyl beta-glucuronide

試薬・触媒・溶媒 1

HCID 18366337Propan-2-one--water (1/1)溶媒

実験手順

Retinoyl fluoride can be mixed with commercially available glucuronic acid. The reaction is carried out in acetone/water to facilitate the solubility of the water-insoluble retinoyl fluoride and the water-soluble glucuronic acid. The reaction takes place in slightly alkaline pH and hence sodium bicarbonate is used in the reaction mixture. Stirring the mixture at room temperature for 20-24 hours followed by acidification of the solution and extraction with ethyl acetate yields retinoyl glucuronide as the major product. Pure all-trans retinoyl β-glucuronide can be obtained by a combination of column and high-performance liquid chromatography (HPLC).

後処理

  1. extractionfollowed by acidification of the solution and extraction with ethyl acetate

出典と根拠

ORDレコード
ord-6187d176f8dd41d0a6a3ec766ba6771b
出典データセット
uspto-grants-1989_08
特許番号
US04855463

関連ノート

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