Sulfuric Acid → Astaxanthin

HRID 843362

반응식

HRID 843362 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 5281224Astaxanthin수율 28.5%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6212Chloroform용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-de78dc77af144fa69f11023380cf6f55
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376717B2

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