Sulfuric Acid → Astaxanthin

HRID 843362

反応式

HRID 843362 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

HCID 5281224Astaxanthin収率 28.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de78dc77af144fa69f11023380cf6f55
出典データセット
uspto-grants-2002_04
特許番号
US06376717B2

関連ノート

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