Water → Dihydrocapsiate

HRID 643211

反応式

HRID 643211 の反応式
[CH3:1][CH:2]([CH3:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[CH2:13](O)[C:14]1[CH:22]=[CH:21][C:19]([OH:20])=[C:16]([O:17][CH3:18])[CH:15]=1.O>CCCCCCC>[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:13][C:14]1[CH:22]=[CH:21][C:19]([OH:20])=[C:16]([O:17][CH3:18])[CH:15]=1)=[O:10])[CH3:12]

参加物

5

反応物 3

HCID 962WaterHCID 62348Vanillyl alcoholHCID 1114708-Methylnonanoic acid

生成物 1

HCID 9873754Dihydrocapsiate収率 98.8%

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒

反応条件

温度
55 °C

実験手順

8-Methylnonanoic acid (1.54 g, 8.95 mmol), vanillyl alcohol (1.34 g, 8.70 mmol), and Novozym 435 (67.0 mg) were measured and placed in a flask (25 ml). The mixture in the flask free of a plug was heated with stirring in an oil bath at 55° C. for 16 hours. After 2 to 3 hours of stirring with heating, attachment of water on the wall of the upper part of the flask was observed. The flask was returned to room temperature, heptane (5 ml) was added to the reaction mixture, and the mixture was stirred for 10 minutes. Novozym 435 and a small amount of precipitated vanillyl alcohol were removed by filtration. The filtrate was concentrated under reduced pressure, and the obtained colorless oil (2.74 g) was analyzed by HPLC to find that dihydrocapsiate was contained in 96.0 area %. The mixture was partitioned with heptane (15 ml) and 10% aqueous citric acid solution (15 ml), and the aqueous layer was further extracted with heptane (15 ml). The combined heptane layer was washed with water (10 ml) and saturated brine (10 ml) and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give a mixture (2.65 g) of dihydrocapsiate and 8-methylnonanoic acid as a colorless oil. As a result of the analysis, the yield of dihydrocapsiate was 97.6%, and the purity was 99.8 area % by HPLC. The mixture contained 1.12 wt % of 8-methylnonanoic acid relative to dihydrocapsiate.

後処理

  1. customplaced in a flask
  2. temperatureThe mixture in the flask free of a plug was heated
  3. stirringAfter 2 to 3 hours of stirring
  4. temperaturewith heating
  5. customwas returned to room temperature
  6. stirringthe mixture was stirred for 10 minutes
  7. customNovozym 435 and a small amount of precipitated vanillyl alcohol were removed by filtration
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe mixture was partitioned with heptane (15 ml) and 10% aqueous citric acid solution (15 ml)
  10. extractionthe aqueous layer was further extracted with heptane (15 ml)
  11. washThe combined heptane layer was washed with water (10 ml) and saturated brine (10 ml)
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customMagnesium sulfate was removed by filtration
  14. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-3c06aa2fcf7d415793b2913b78f1d5cf
出典データセット
uspto-grants-2010_04
特許番号
US07700331B2

関連ノート

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