Water → VIOLERYTHRIN

HRID 1283577Notes

Reaction equation

HRID 1283577 reaction equation
[CH3:1][C:2]1[C:6](=[O:7])[CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:40])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:39])=[CH:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](\[CH3:38])/[CH:22]=[CH:23]/[CH:24]=[C:25](\[CH3:37])/[CH:26]=[CH:27]/[C:28]1[C:33]([CH3:35])([CH3:34])[CH2:32][C:30](=[O:31])[C:29]=1[CH3:36].C1(C)C=CC=CC=1.[Se](=O)=[O:49].[OH2:51]>>[CH3:36][C:29]1[C:30](=[O:31])[C:32](=[O:51])[C:33]([CH3:35])([CH3:34])[C:28]=1/[CH:27]=[CH:26]/[C:25](/[CH3:37])=[CH:24]/[CH:23]=[CH:22]/[C:21](/[CH3:38])=[CH:20]/[CH:19]=[CH:18]/[CH:17]=[C:16](\[CH3:39])/[CH:15]=[CH:14]/[CH:13]=[C:12](\[CH3:40])/[CH:11]=[CH:10]/[C:3]1[C:4]([CH3:8])([CH3:9])[C:5](=[O:49])[C:6](=[O:7])[C:2]=1[CH3:1]

Participants

5

Reactant 4

HCID 962Water2×HCID 1140TolueneHCID 24007Selenium DioxideHCID 10414836HCID 10414836, compound

Product 1

HCID 5380111VIOLERYTHRIN

Procedure

0.3 g. of all-trans di-nor-canthaxanthin are dissolved in 50 ml. of toluene. After the addition of 10.2 g. of selenium dioxide and 0.7 ml. of water, the mixture is heated to boiling for 16 hours under reflux conditions. The mixture is then introduced into water and extracted with toluene. After evaporation of the toluene extract, there is obtained di-nor-astacin [2,2'-di-nor-β-carotene-3,3',4,4'-tetraone; violerythrin] which, after recrystallization by adsorption on silica gel, has a mass spectrum m/e of 564.

Workup

  1. additionAfter the addition of 10.2 g
  2. extractionextracted with toluene
  3. customAfter evaporation of the toluene
  4. extractionextract

Sources & evidence

ORD record
ord-135773be5cfe481a9714e1f8d74d24a9
Source dataset
uspto-grants-1976_08
Patent number
US03975445

Reaction notes

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