Retinol → Retinol, acetate

HRID 1722492

Reaction equation

[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](/[CH3:33])=[CH:13]\[CH:14]=[CH:15]\[C:16](\[CH3:32])=[CH:17]/[CH2:18][O:19][C@@H:20]1[O:25][C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H:21]1O.CC1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/CO>>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:33])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:32])=[CH:17]/[CH2:18][O:19][C:20]([CH3:21])=[O:25]

Participants

Reactant 2

HCID 445354Retinol

HCID 6440956Retinylglucuronide

Product 1

HCID 638034Retinol, acetate

Procedure

The starting materials for the preparation of retinyl β-glucuronide include retinol that can be obtained as an oil by saponification of commercially available retinyl acetate, and methyl (2,3,4-tri-O-acetyl glucopyranosyl bromide)-uronate that can be synthesized from commercially available 6,3-glucuronolactone by known procedures (Bollenback et al. J. Amer. Chem. Soc. 77: 3310-3315, 1955). The reaction is carried out in the presence of silver carbonate by stirring at room temperature for 20-24 hours. The resulting product is a mixture of unconverted retinol and the fully protected glucuronide of retinol. To obtain the free glucuronide, the crude mixture is saponified without separating the other products and then the products are separated by a combination of column chromatography and HPLC.

Sources & evidence

ORD record: ord-aea6f7adb78f4a1a9863e494d7517693
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04855463

Linked notes

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