Astaxanthin bis(trimethylsilyl)ether → Astaxanthin

HRID 1381322

반응식

HRID 1381322 반응식
[CH3:1][C:2]1[C:7](=[O:8])[C@@H:6]([OH:9])[CH2:5][C:4]([CH3:11])([CH3:10])[C:3]=1/[CH:12]=[CH:13]/[C:14](/[CH3:44])=[CH:15]/[CH:16]=[CH:17]/[C:18](/[CH3:43])=[CH:19]/[CH:20]=[CH:21]/[CH:22]=[C:23](\[CH3:42])/[CH:24]=[CH:25]/[CH:26]=[C:27](\[CH3:41])/[CH:28]=[CH:29]/[C:30]1[C:36]([CH3:38])([CH3:37])[CH2:35][C@H:34]([OH:39])[C:32](=[O:33])[C:31]=1[CH3:40].C[Si](O[Si](C)(C)C)(C)C>CO>[CH3:40][C:31]1[C:32](=[O:33])[C@@H:34]([OH:39])[CH2:35][C:36]([CH3:37])([CH3:38])[C:30]=1/[CH:29]=[CH:28]/[C:27](/[CH3:41])=[CH:26]/[CH:25]=[CH:24]/[C:23](/[CH3:42])=[CH:22]/[CH:21]=[CH:20]/[CH:19]=[C:18](\[CH3:43])/[CH:17]=[CH:16]/[CH:15]=[C:14](\[CH3:44])/[CH:13]=[CH:12]/[C:3]1[C:4]([CH3:11])([CH3:10])[CH2:5][C@H:6]([OH:9])[C:7](=[O:8])[C:2]=1[CH3:1]

참가 물질

3

반응물 1

HCID 131714651Astaxanthin bis(trimethylsilyl)ether

생성물 1

HCID 5281224Astaxanthin

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The crude product of the astaxanthin bis(trimethylsilyl)ether was taken up in 20 ml of methanol and boiled at reflux under argon for 4 hours. The mixture was left to cool to room temperature and was then cooled to -20° C., there being obtained a red-violet precipitation of 4.5 g of crude astaxanthin. Concentration of the mother liquor yielded about 3 g of solid red residue from which a further 0.4 g of crude astaxanthin was obtained by chromatography on silica gel with methylene chloride/diethyl ether (9:1) as the eluent and under an argon pressure of 0.2-0.4 bar. The resulting crude astaxanthin (4.9 g) was dissolved in 10 ml of methylene chloride and chromatographed on silica gel with methylene chloride/diethyl ether (9:1) as the eluent and an argon pressure of 0.2-0.4 bar. The uniform fractions were concentrated and recrystallized from methylene chloride/methanol, there being obtained 2.87 g of all-trans astaxanthin (purity about 90%); m.p. 216°-219° C.; yield 48% based on canthaxanthin.

후처리

  1. temperatureat reflux under argon for 4 hours
  2. waitThe mixture was left
  3. temperaturewas then cooled to -20° C.
  4. customthere being obtained
  5. customa red-violet precipitation of 4.5 g of crude astaxanthin

출처 및 근거

ORD 기록
ord-0027c0e6911947a6865f809cba848697
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04585885

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