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Water → Astaxanthin

HRID 842349
Notes
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Reaction equation

HRID 842349 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(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH2:57]>C(Cl)(Cl)Cl>[CH3:38][C:30]1[C:31](=[O:57])[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 656671Sodium PyrosulfiteHCID 5280899ZeaxanthinHCID 23668195Sodium Bromate

Product 1

HCID 5281224Astaxanthin

Reagents, catalysts & solvents 1

HCID 6212Chloroform
Solvent

Conditions

Temperature
50 °C

Procedure

To a suitable flask was added 20 grams of a natural product mixture containing 12.2 grams zeaxanthin (21.4 mmoles) slurried in 200 ml of chloroform. To this mixture was added a solution of 8.05 gms (53.3 mmoles) of sodium bromate. To this mixture was added dropwise over three hours at temperatures between 20 to 30° C., 8 ml of a solution prepared by dissolving 6.66 gms of sodium metabisulfite in 24 ml of water. After addition, the reaction mixture was filtered through Celite and the aqueous phase was separated. The chloroform was removed by vacuum evaporation at 40-42° C. The resulting slightly wet solid was added to 190 ml of warm (50° C.) 95% ethanol. The mixture was stirred and cooled slowly to −10° C. The resulting solid was filtered off and dried under vacuum to produce 8.8 grams (72.14%) yield of astaxanthin product containing greater than 25% astaxanthin.

Workup

  1. additionTo this mixture was added dropwise over three hours at temperatures between 20 to 30° C.
  2. additionAfter addition
  3. filtrationthe reaction mixture was filtered through Celite
  4. customthe aqueous phase was separated
  5. customThe chloroform was removed by vacuum evaporation at 40-42° C
  6. additionThe resulting slightly wet solid was added to 190 ml
  7. temperaturecooled slowly to −10° C
  8. filtrationThe resulting solid was filtered off
  9. customdried under vacuum

Sources & evidence

ORD record
ord-e0d7ba4fe0924ffea2401f5a702b5b72
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06372946B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes