β,β-Carotene-4,4'-diol → Canthaxanthin

HRID 2057738

Reaktionsgleichung

Reaktionsgleichung von HRID 2057738
Br([O-])(=O)=O.[Na+].[CH3:6][C:7]1[CH:12]([OH:13])[CH2:11][CH2:10][C:9]([CH3:15])([CH3:14])[C:8]=1/[CH:16]=[CH:17]/[C:18](/[CH3:47])=[CH:19]/[CH:20]=[CH:21]/[C:22](/[CH3:46])=[CH:23]/[CH:24]=[CH:25]/[CH:26]=[C:27](\[CH3:45])/[CH:28]=[CH:29]/[CH:30]=[C:31](\[CH3:44])/[CH:32]=[CH:33]/[C:34]1[C:39]([CH3:41])([CH3:40])[CH2:38][CH2:37][CH:36]([OH:42])[C:35]=1[CH3:43]>O.ClCCCl.BrBr>[CH3:43][C:35]1[C:36](=[O:42])[CH2:37][CH2:38][C:39]([CH3:40])([CH3:41])[C:34]=1/[CH:33]=[CH:32]/[C:31](/[CH3:44])=[CH:30]/[CH:29]=[CH:28]/[C:27](/[CH3:45])=[CH:26]/[CH:25]=[CH:24]/[CH:23]=[C:22](\[CH3:46])/[CH:21]=[CH:20]/[CH:19]=[C:18](\[CH3:47])/[CH:17]=[CH:16]/[C:8]1[C:9]([CH3:15])([CH3:14])[CH2:10][CH2:11][C:12](=[O:13])[C:7]=1[CH3:6]

Komponenten

6

Edukt 2

HCID 11757703β,β-Carotene-4,4'-diolHCID 23668195Sodium Bromate

Produkt 1

HCID 5281227CanthaxanthinAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittel2×HCID 962WaterLösungsmittelHCID 24408BromineLösungsmittel

Versuchsvorschrift

1.5 g of sodium bromate dissolved in 20 ml of water is added to 1.5 g of isozeaxanthin dissolved in 250 ml of 1,2-dichloroethane. While stirring, 10 ml of 1,2-dichloroethane in which 30 mg of bromine is dissolved is dripped in over a period of 30 minutes. The pH of the aqueous phase is 5.6. After stirring for 1 hour at room temperature, the phases are separated, the 1,2-dichloroethane is washed with sodium bicarbonate solution and water and dried, and the solvent is distilled off under reduced pressure. 20 ml of methanol is added to the residue and the whole stirred for 10 minutes at 50° C. After cooling, filtration gives 1.36 g (92% of theory) of canthaxanthin.

Aufarbeitung

  1. customis dripped in over a period of 30 minutes
  2. stirringAfter stirring for 1 hour at room temperature
  3. customthe phases are separated
  4. washthe 1,2-dichloroethane is washed with sodium bicarbonate solution and water
  5. customdried
  6. distillationthe solvent is distilled off under reduced pressure
  7. addition20 ml of methanol is added to the residue
  8. stirringthe whole stirred for 10 minutes at 50° C
  9. temperatureAfter cooling
  10. filtrationfiltration

Quellen und Nachweise

ORD-Eintrag
ord-88ae006b4ba44958a96f415ac6fdc669
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04212827

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