Cholesterol → Cholesteryl Oleate

HRID 1587650

Reaction equation

HRID 1587650 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[C:29](O)(=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C(CC(C)(C)C)(C)C>CCOCC>[CH3:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]/[CH:38]=[CH:37]\[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][C:29]([O:19][C@@H:18]1[CH2:17][C:16]2[C@@:22]([CH3:23])([C@@H:24]3[C@@H:13]([CH2:14][CH:15]=2)[C@@H:12]2[CH2:11][CH2:10][C@H:9]([C@@H:7]([CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH3:8])[C@@:27]2([CH3:28])[CH2:26][CH2:25]3)[CH2:21][CH2:20]1)=[O:47]

Participants

5

Reactant 3

HCID 5997CholesterolHCID 109072,2,4-TrimethylpentaneHCID 445639Oleic Acid

Product 1

HCID 5283632Cholesteryl Oleate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g of cholesterol, 22 g of oleic acid, 50 ml of isooctane and 200 ml (50,000 U) of an aqueous solution of lipase MY was stirred at 200 rpm for 18 hours. Thereafter, ether was added and the mixture was washed with aqueous sodium bicarbonate to remove the aqueous layer. After several repetitions of this procedure, the ether layer was dried on anhydrous sodium sulfate. The ether was then distilled off to give cholesteryl oleate, which was a white semi-transparent crude product, in 96.3% purity and in a yield of 16.0 g (95.0%).

Workup

  1. washthe mixture was washed with aqueous sodium bicarbonate
  2. customto remove the aqueous layer
  3. dry with materialAfter several repetitions of this procedure, the ether layer was dried on anhydrous sodium sulfate
  4. distillationThe ether was then distilled off

Sources & evidence

ORD record
ord-b156ad3af2fa44838c586936ad0a1aa4
Source dataset
uspto-grants-1993_06
Patent number
US05219733

Linked notes

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