Sodium Hydroxide → Cholesterol

HRID 2354476Notes

Reaction equation

HRID 2354476 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[OH-:28].[Na+]>C(O)C>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@H:18]([CH2:19][CH2:20]2)[OH:28])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5283630Coprostane

Product 1

HCID 5997Cholesterol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Feces (day 14) (25 mg) were weighed and placed in a test tube (15 mL) equipped with a screw cap, and an internal standard substance (5β-cholestane) (0.1 μmol) and a 90% ethanol solution containing 1N sodium hydroxide (1 mL) were added thereto. The mixture was heated at 80° C. by means of a block heater. One hour after, distilled water (0.5 mL) was added, and neutral sterols were taken through two rounds of extraction by use of petroleum ether (2.5 mL). The resultant extract was washed with distilled water (7.5 mL), dehydrated over sodium sulfate, and dried to solid under nitrogen gas flow. The recovered neutral sterols were trimethylsilylated, and analyzed through gas chromatography under the following conditions (Table 28).

Workup

  1. customplaced in a test tube
  2. custom(15 mL) equipped with a screw
  3. customcap
  4. additionwere added
  5. distillationOne hour after, distilled water (0.5 mL)
  6. additionwas added
  7. extractionneutral sterols were taken through two rounds of extraction by use of petroleum ether (2.5 mL)
  8. extractionThe resultant extract
  9. washwas washed with distilled water (7.5 mL)
  10. customdried to solid under nitrogen gas flow

Sources & evidence

ORD record
ord-2ffeb8e588bd4103b403fcde0c1033ae
Source dataset
uspto-grants-2010_07
Patent number
US07754204B2

Reaction notes

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