Water → Astaxanthin

HRID 843363

Reaction equation

HRID 843363 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].Cl([O-])(=O)=[O:44].[Na+].[I-].[Na+].S(=O)(=O)(O)O.[OH2:55]>C(Cl)(Cl)Cl>[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

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 516902Sodium ChlorateHCID 5280899Zeaxanthin

Product 1

HCID 5281224Astaxanthin

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Zeaxanthin (50 mg) was stirred in 20 ml of chloroform under nitrogen. To this stirred mixture, 200 mg of sodium chlorate and 50 mg of sodium iodide in 10 ml of water was added. The mixture was acidified slowly with 1 ml of 27% sulfuric acid. The reaction was stirred at room temperature. After 5 hours, a significant quantity of astaxanthin had formed. The reaction was worked up by addition of 1 ml of 40% sodium hydroxide, separation of the organic solution and evaporation to yield astaxanthin.

Sources & evidence

ORD record
ord-5a002155ec6d4801ac300abd4f20e80b
Source dataset
uspto-grants-2002_04
Patent number
US06376717B2

Linked notes

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