Sulfuric Acid → Astaxanthin

HRID 843362

Reaction equation

HRID 843362 reaction equation
[CH3:1][C:2]1[CH2:7][C@@H:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[C:3]=1/[CH:11]=[CH:12]/[C:13](/[CH3:42])=[CH:14]/[CH:15]=[CH:16]/[C:17](/[CH3:41])=[CH:18]/[CH:19]=[CH:20]/[CH:21]=[C:22](\[CH3:40])/[CH:23]=[CH:24]/[CH:25]=[C:26](\[CH3:39])/[CH:27]=[CH:28]/[C:29]1[C:34]([CH3:36])([CH3:35])[CH2:33][C@H:32]([OH:37])[CH2:31][C:30]=1[CH3:38].Br([O-])(=O)=[O:44].[Na+].S(=O)(=O)(O)O.[Br-].[K+].[OH-:55].[Na+]>C(Cl)(Cl)Cl.O>[CH3:38][C:30]1[C:31](=[O:55])[C@@H:32]([OH:37])[CH2:33][C:34]([CH3:36])([CH3:35])[C:29]=1/[CH:28]=[CH:27]/[C:26](/[CH3:39])=[CH:25]/[CH:24]=[CH:23]/[C:22](/[CH3:40])=[CH:21]/[CH:20]=[CH:19]/[CH:18]=[C:17](\[CH3:41])/[CH:16]=[CH:15]/[CH:14]=[C:13](\[CH3:42])/[CH:12]=[CH:11]/[C:3]1[C:4]([CH3:9])([CH3:10])[CH2:5][C@H:6]([OH:8])[C:7](=[O:44])[C:2]=1[CH3:1]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 253877Potassium BromideHCID 5280899ZeaxanthinHCID 23668195Sodium Bromate

Product 1

HCID 5281224AstaxanthinYield 28.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

Zeaxanthin (6.24 gm, 11 mmole) was slurried in 110 ml of chloroform under nitrogen and cooled on ice. To this stirred mixture, was added a solution of 6.14 gm (51.6 mmole) sodium bromate in 35 ml of water and acidified with 1 ml of 50% sulfuric acid. The three phase mixture was cooled on ice and 4 ml of a solution containing 4.84 gm (32.1 mmole) of potassium bromide in 15 ml of water was added rapidly to begin the reaction. After 1 hour, 7 ml of 3 N sodium hydroxide was added and the mixture was stirred for 15 minutes. The mixture was filtered over celite and the phases were separated. The organic layer was washed with basic water and separated. The chloroform was removed under vacuum at around 40° C. until a thick slurry remained. Ethanol (90 ml) was added and the remaining chloroform was removed by vacuum distillation. The reaction mixture was cooled and the product collected by filtration to yield 1.78 grams (28.5% yield) astaxanthin.

Workup

  1. temperaturecooled on ice
  2. additionwas added rapidly
  3. customthe reaction
  4. filtrationThe mixture was filtered over celite
  5. customthe phases were separated
  6. washThe organic layer was washed with basic water
  7. customseparated
  8. customThe chloroform was removed under vacuum at around 40° C. until a thick slurry
  9. additionEthanol (90 ml) was added
  10. customthe remaining chloroform was removed by vacuum distillation
  11. temperatureThe reaction mixture was cooled
  12. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-de78dc77af144fa69f11023380cf6f55
Source dataset
uspto-grants-2002_04
Patent number
US06376717B2

Linked notes

Loading…