Beta-Carotene → 9-cis-beta-Carotene

HRID 1033138Notes

Reaction equation

HRID 1033138 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][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][CH2:31][CH2:30][C:29]=1[CH3:36]>CCCCCC>[CH3:36][C:29]1[CH2:30][CH2:31][CH2:32][C:33]([CH3:34])([CH3:35])[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](/[CH:15]=[CH:14]/[CH:13]=[C:12](\[CH:11]=[CH:10]\[C:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])/[CH3:40])\[CH3:39]

Participants

3

Reactant 1

HCID 5280489Beta-Carotene

Product 1

HCID 98286269-cis-beta-Carotene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

High purity beta-carotene from Example I was dissolved in a minimal amount of warm (about 40°-50° C.) hexane to achieve saturation. The solution was then chilled, typically to about -20° C., which caused the preferential crystallization of the trans-isomer of beta-carotene. The crystals were then separated from the supernatant solution by filtration through a hydrophobic 0.22 μ nylon membrane filter (Micron Separations, Inc., Cambridge, MA). Chromatograms of representative preparations of the supernatant enriched in the 9-cis isomer (approximately 75-80% 9-cis and 15-20% all-trans) and of the crystals containing the all-trans isomer (approximately 80-85% all-trans and 10-15% 9-cis) are shown in FIGS. 2B and 2C, respectively.

Workup

  1. customthe preferential crystallization of the trans-isomer of beta-carotene
  2. customThe crystals were then separated from the supernatant solution by filtration through a hydrophobic 0.22 μ nylon membrane
  3. filtrationfilter (Micron Separations, Inc., Cambridge, MA)
  4. additioncontaining the all-trans isomer (approximately 80-85% all-trans and 10-15% 9-cis)

Sources & evidence

ORD record
ord-ab9200a53bd244ffbd1c7a5b598f8f9f
Source dataset
uspto-grants-1994_05
Patent number
US05310554

Reaction notes

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