4-methoxycinnamoyl glycerol | 55380-00-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-methoxycinnamoyl glycerol
• 英文别名: p-methoxycinnamoyl glycerol；2,3-Dihydroxypropyl 3-(4-methoxyphenyl)prop-2-enoate
• CAS: 55380-00-2
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: TWNMUIOZHQVLGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲氧基肉桂酸 、 4-methoxycinnamoyl glycerol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 1,3-di(4-methoxycinnamoyl) glycerol
  参考文献：
  名称：

  肉桂酰基甘油形成的动力学

  摘要：

  AbstractThe esterifications of glycerol with cinnamic acid, 2‐methoxy cinnamic acid, and 4‐methoxy cinnamic acid were investigated in batch reactions. Conversions of over 50% were achieved for cinnamic acid and 4‐methoxy cinnamic acid within 8 h. After 24 h, conversions of over 80% were obtained for cinnamic acid and 4‐methoxy cinnamic acid. Conversions of 33 and 40% were observed for 2‐methoxy cinnamic acid after 8 and 24 h, respectively. These reactions were modeled by a system of sequential first‐order rate expressions. Kinetic parameters were estimated from experimental data fit to the model equations.

  DOI：

  10.1007/s11746-007-1189-3
• 作为产物：
  描述：

  (E)-3-(4-Methoxy-phenyl)-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 在 硼酸 作用下， 以 乙二醇甲醚 为溶剂， 反应 1.0h， 生成 4-methoxycinnamoyl glycerol
  参考文献：
  名称：

  降血脂药的研究。1.烷氧基肉桂酸衍生物的合成及其降血脂活性。

  摘要：

  合成了110多种烷氧基肉桂酸衍生物，并在大鼠筛选系统中评估了它们的降血脂活性。发现肉桂酸，α-甲基肉桂酸及其各种具有较高对烷氧基取代基的酯具有比氯贝贝特更高或相当的降血脂活性。适当的长度（C12-C16）和烷氧基取代基的对位似乎对活性至关重要。一些活性对烷氧基肉桂酸的氯乙基和甲基丙烯酰氧基乙基酯以及甘油单酯比相应的游离酸更具活性。

  DOI：

  10.1021/jm00175a010

文献信息

• Ultrasonic-promoted enzymatic preparation, identification and multi-active studies of nature-identical phenolic acid glycerol derivatives
  作者：Teng Sun、Haiping Zhang、Zhe Dong、Zengshe Liu、Mingming Zheng

  DOI：10.1039/c9ra09830e

  日期：——

  Phenolic acid glycerols (PAGs) are a group of rare phytochemicals found from potato periderm, which show great potential in the food, cosmetic and pharmaceutical industries. In this study, seven PAGs were enzymatically synthesized via transesterification of ethyl phenates (EPs) with glycerol by ultrasonic promotion. The conversions of 88.1–98.5% could be obtained in 1–9 h. Compared with the conventional

  酚酸甘油 (PAGs) 是从马铃薯外皮中发现的一组稀有植物化学物质，在食品、化妆品和制药行业中显示出巨大的潜力。在这项研究中，通过超声波促进酚乙酯 (EPs) 与甘油的酯交换酶促合成了七种 PAG 。88.1-98.5% 的转化率可以在 1-9 小时内获得。与传统搅拌方法相比，超声辅助催化效率显着提高了11.0-44.0倍。与母体酚酸 (PA) 相比，脂质过氧化抑制活性增加了 8.1 倍和 14.4 倍。此外，咖啡酰甘油和阿魏酰甘油对大肠杆菌表现出优异的抗菌活性与相应的 PA 相比，最小抑制浓度 (MIC) 降低了 4-16 倍。与相应的 PA 相比，PAG 还可以吸收更广泛和更高量的有害 UV-B 射线。目前用于简便合成多功能 PAG 的策略为天然植物化学物质和新型成分的开发和应用铺平了道路。
• Ultrasonic pretreatment for lipase-catalyzed synthesis of 4-methoxy cinnamoyl glycerol
  作者：Pingmei Guo、Chang Zheng、Fenghong Huang、Mingming Zheng、Qianchun Deng、Wenlin Li

  DOI：10.1016/j.molcatb.2013.04.004

  日期：2013.9

  4-Methoxy cinnamoyl glycerol (4MCG) is a very promising UV filters material in personal care products. In order to effectively improve the yield of 4MCG, a systematic study on ultrasonic pretreatment enzymatic esterification for 4MCG products was carried out. An ultrasonic frequency of 35 kHz, ultrasonic power of 150 W and ultrasound irradiation time of 1.5 h was determined to guarantee satisfactory

  4-甲氧基肉桂酰甘油（4MCG）是个人护理产品中非常有前途的紫外线过滤材料。为了有效提高4MCG的收率，对4MCG产品进行超声波预处理酶促酯化进行了系统的研究。确定超声频率为35 kHz，超声功率为150 W，超声辐照时间为1.5 h，以确保令人满意的酯化度和脂肪酶活性。在65°C的有机溶剂体系中以4MCA与甘油的摩尔比为1：5，酶的量为15 mg / mL达到最佳产量，在48 h和24 h后单酯收率分别达到66％和55％以上超声波预处理的反应分别。研究了实验动力学数据。反应是通过顺序的一阶速率表达式系统建模的，动力学参数是根据与模型方程拟合的实验数据估算的。结果表明，在超声预处理过程（24 h）中，单酯收率是机械搅拌过程中单酯收率的1.5倍以上，而对脂酶活性没有实质性损害。在转化率和单酯收率方面，超声预处理的酶法明显优于酶法和化学法的机械搅拌。这些结果对应用超声预处理方法制备4MCG具有
• CINNAMIC ACID/GLYCEROL ADDUCT, ULTRAVIOLET ABSORBER, AND DERMATOLOGIC PREPARATION
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0539601A1

  公开（公告）日：1993-05-05

  A cinnamic acid/glycerol adduct represented by general formula (1), an ultraviolet absorber, and a dermatologic preparation containing the same, wherein G corresponds to 1 mol of glycerol; e represents an average molar number of addition and is at least one; R represents hydrogen or a fatty chain; n and k represent each 0 to 3 and 1 ≦ n + k ≦ 3 ; and X represents hydrogen, ion, fatty chain or Gm, wherein G is defined above and m represents an average molar number of addition and is at least one. The adduct has a high water-solubility and good safety and stability.

  一种由通式（1）表示的肉桂酸/甘油加合物、一种紫外线吸收剂以及一种含有该加合物的皮肤病制剂，其中 G 相当于 1 摩尔甘油；e 代表平均加成摩尔数，且至少为一个；R 代表氢或脂肪链；n 和 k 分别代表 0 至 3，且 1 ≦ n + k ≦ 3；X 代表氢、离子、脂肪链或 Gm，其中 G 如上文所定义，m 代表平均加成摩尔数，且至少为一个。这种加合物具有很高的水溶性和良好的安全性和稳定性。
• AGENTS FOR INHIBITING OR RESTORING SKIN DAMAGE CAUSED BY DRYING AND METHOD OF EVALUATING THE SAME
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP1354580A1

  公开（公告）日：2003-10-22

  External preparations for the skin which contain, as active ingredients, substances capable of preventing a reduction in the expression of the filaggrin gene in cultured human keratinocytes as induced by exposure to a gaseous phase (for example, betaines, polyols, crude drugs, and substances having an antioxidant action).

  皮肤外用制剂，其活性成分中含有能够防止培养的人类角质细胞因暴露于气相而导致丝胶基因表达减少的物质（例如甜菜碱、多元醇、粗制药物和具有抗氧化作用的物质）。
• Oil-water mixed composition
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP1468663A2

  公开（公告）日：2004-10-20

  An oil-water mixed composition is consisted of a solid or semisolid oil phase at room temperature, and a water phase which is dispersed into the oil phase. The water phase contains a humectant and is solid or semisolid at room temperature. Preferably, the oil phase contains hydrophobic silica, dextrin fatty acid ester or polyvalent alcohol oligo ester of long chain monocarboxylic acid and long chain dicarboxylic acid. The oil-water mixed composition is superior in stability with passage of time and safety. In addition, this composition has demonstrated little stickiness and sensation of unsuitability for skin, and has much emollient effect (i.e., to prevent the skin from dryness) and is persistent in preserving its emollient effect.

  油水混合组合物由室温下的固态或半固态油相和分散在油相中的水相组成。水相含有保湿剂，在室温下为固态或半固态。油相最好含有疏水性二氧化硅、糊精脂肪酸酯或长链单羧酸和长链二羧酸的多价醇寡酯。 这种油水混合组合物随着时间的推移具有更高的稳定性和安全性。此外，这种组合物对皮肤的粘性和不适宜感很小，具有很强的润肤效果（即防止皮肤干燥），并能持久保持其润肤效果。