HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Retinoyl beta-glucuronide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Glucuronic Acid | HCID 65041 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl fluoride | HCID 5378594 | — |
| Solvent | Propan-2-one--water (1/1) | HCID 18366337 | — |
| Product | Retinoyl beta-glucuronide | HCID 5281877 | — |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04855463 |
| Source dataset | uspto-grants-1989_08 |
| ORD ID | ord-6187d176f8dd41d0a6a3ec766ba6771b |
| Source note | uspto-grants-1989_08 |