(Rac)-propionic acid 1-(4-propionoxy-phenyl)-allyl ester | 53890-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (Rac)-propionic acid 1-(4-propionoxy-phenyl)-allyl ester
• 英文别名: [4-(1-propanoyloxyprop-2-enyl)phenyl] propanoate
• CAS: 53890-22-5
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: ZWFJRXCWFRDTIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Rac)-propionic acid 1-(4-propionoxy-phenyl)-allyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 Propionic acid 1-(4-propionyloxy-phenyl)-propyl ester
  参考文献：
  名称：

  Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

  摘要：

  1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 mu M. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.070
• 作为产物：
  描述：

  1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (Rac)-propionic acid 1-(4-propionoxy-phenyl)-allyl ester
  参考文献：
  名称：

  Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

  摘要：

  1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 mu M. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.070

文献信息

• Flavorant compositions
  申请人：Givaudan Roure (International) SA

  公开号：US06476252B1

  公开（公告）日：2002-11-05

  The invention is related to a flavorant composition containing 1′-acetoxychavicol acetate and 1′-acetoxyeugenol acetate derivatives thereof as well as a flavorant acceptable carrier. The flavorant composition may be used for flavoring foods, beverages or healthcare products with warm/hot, spicy and pungent sensations related to Galangal.

  这项发明涉及一种含有1'-乙酰氧基巴豆酚醋酸酯和1'-乙酰氧基丁香酚醋酸酯衍生物的风味剂组合物，以及可接受的风味剂载体。该风味剂组合物可用于赋予食品、饮料或保健产品温暖/辣味和刺激感，与高良姜相关。
• Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages
  作者：Hisashi Matsuda、Shin Ando、Toshio Morikawa、Shinya Kataoka、Masayuki Yoshikawa

  DOI：10.1016/j.bmcl.2005.01.070

  日期：2005.4

  1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 mu M. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity. (c) 2005 Elsevier Ltd. All rights reserved.