四甲基姜黄素 | 52328-97-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: 四甲基姜黄素
• 英文名称: (1E,6E)-1,7-bis(3,4-dimethoxyphenyl)-4,4-dimethylhepta-1,6-diene-3,5-dione
• 英文别名: FLLL31；Tetramethylcurcumin
• CAS: 52328-97-9
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: VMMZAMVBGQWOHT-UTLPMFLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰丙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 72.0h， 生成 四甲基姜黄素
  参考文献：
  名称：

  Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents

  摘要：

  Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(.+)), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS(.+)-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.

  DOI：

  10.1007/s00044-012-0116-9

文献信息

• [EN] CURCUMIN ANALOGS AS DUAL JAK2/STAT3 INHIBITORS AND METHODS OF MAKING AND USING THE SAME<br/>[FR] ANALOGUES DE LA CURCUMINE EN TANT QU'INHIBITEURS DOUBLES DE JAK2/STAT3 ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：UNIV OHIO STATE RES FOUND

  公开号：WO2010121007A1

  公开（公告）日：2010-10-21

  Curcumin analogues and methods of making and using the same are disclosed.

  姜黄素类似物及其制备和使用方法已被披露。
• [EN] A PERSONAL CARE COMPOSITION<br/>[FR] COMPOSITION DE SOINS PERSONNELS
  申请人：UNILEVER NV

  公开号：WO2018149578A1

  公开（公告）日：2018-08-23

  Disclosed is a personal care composition and a method of providing antiperspirant and anti-inflammation using certain curcuminoid derivatives. The composition comprises: (i) a compound of the Formula 1 Ar-CHnCHn-X.C(R)2-X.CHnCHn-Ar (Formula 1) wherein Ar is a substituted or unsubstituted phenyl group; R is H or CH3; X is CH(OH) group or C=O group; n has the value 1 or 2; and, (ii) a topically acceptable base comprising at least 0.1% of a fragrance wherein, when n=1, the compound of (Formula 1) is 1E,6E)-1,7-bis(3,4- dimethoxyphenyl)-4,4-dimethylhepta-1,6-diene-3,5-dione (Formula 2), and when n=2, the compound of (Formula 1) is 1,7-bis(4-hydroxy-3- methoxyphenyl) heptane-3,5-diol (Formula 4) or is 1,7-bis (3,4-dimethoxyphenyl)-4,4-dimethylheptane-3,5-diol (Formula 5).

  本文揭示了一种个人护理组合物和利用特定姜黄素衍生物提供止汗剂和抗炎作用的方法。该组合物包括：(i) 公式1 Ar-CHnCHn-X.C(R)2-X.CHnCHn-Ar（公式1）中的化合物，其中Ar是取代或未取代的苯基；R是H或CH3；X是CH(OH)基团或C=O基团；n的取值为1或2；以及，(ii) 至少含有0.1%香料的局部可接受基质，当n=1时，化合物（公式1）为1,7-双（3,4-二甲氧基苯基）-4,4-二甲基庚烯-1,6-二烯-3,5-二酮（公式2），当n=2时，化合物（公式1）为1,7-双（4-羟基-3-甲氧基苯基）庚烷-3,5-二醇（公式4）或为1,7-双（3,4-二甲氧基苯基）-4,4-二甲基庚烷-3,5-二醇（公式5）。
• Study on the Synthesis of Methylated Reference and Their Application in the Quantity of Curcuminoids Using Single Reference Liquid Chromatography Based on Relative Molar Sensitivity
  作者：Miki Takahashi、Koji Morimoto、Yuzo Nishizaki、Naoko Masumoto、Naoki Sugimoto、Kyoko Sato、Koichi Inoue

  DOI：10.1248/cpb.c21-00621

  日期：2022.1.1

  We report on the recommendation of the simple and versatility of methylated reference (MR) to improve applications in the single reference (SR)-LC based on relative molar sensitivity (RMS). Three curcuminoids (Curs) such as curcumin, demethoxycurcumin and bisdemethoxycurcumin in turmeric products were determined using authentic standards and methylated curcumin. In addition, high-speed countercurrent chromatography (HSCCC) purification is necessary to separate Curs for indicating the RMS. For HSCCC separation, a biphasic solvent system was used to obtain these fractions, which were then subjected to 1H quantitative NMR to determine their contents in each test solution. Using these solutions, the RMS of Curs are calculated from slopes ratios of calibration curves (three ranges from 0–100 µmol/L, r2 > 0.998). The averaged RMS of Curs were 8.92 (relative standard deviation (RSD), 1.17%), 8.97 (2.18%), and 9.61 (0.77%), respectively. Cur concentrations in turmeric products can be determined using RMS, peak area, and MR content added in these samples. This proposed method, which is based on chemical methylation and the SR-LC assay has been successfully applied for the simple and reliable estimation of Curs in turmeric products.

  我们报告了使用甲基化参考物质（MR）来提高基于相对摩尔灵敏度（RMS）的单一参考（SR）-LC应用的简单性和多功能性的推荐。在姜黄产品中，使用真实标准和甲基化姜黄素测定了三种姜黄素（Curs），即姜黄素、去甲氧基姜黄素和双去甲氧基姜黄素。此外，高速逆流色谱（HSCCC）纯化是分离姜黄素以指示RMS所必需的。为进行HSCCC分离，使用了双相溶剂系统，以获得这些分级，然后对其进行1H定量核磁共振（NMR）分析，以确定每个测试溶液中的含量。利用这些溶液，姜黄素的RMS是通过校准曲线的斜率比计算得出的（三个范围为0–100 µmol/L，r² > 0.998）。姜黄素的平均RMS分别为8.92（相对标准偏差（RSD），1.17%），8.97（2.18%）和9.61（0.77%）。姜黄产品中的姜黄素浓度可以通过RMS、峰面积和这些样本中添加的MR含量来确定。该方法基于化学甲基化和SR-LC测定，已成功应用于对姜黄产品中姜黄素的简单而可靠的估算。
• CURCUMIN COMPOSITIONS AND USES THEREOF
  申请人：Liu Zhongfa

  公开号：US20130143969A1

  公开（公告）日：2013-06-06

  A composition and method of increasing the bioavailability of curcumin is provided. A synergistic combination of excipient polymers provides increased bioavailability thereby increasing the plasma concentration of curcumin and its metabolite curcumin O-glucuronide. The curcumin pharmaceutical compositions are suitable for modifying DNA methylation and treating diseases such as cancer.

  提供了一种增加姜黄素生物利用度的组合物和方法。共同作用的赋形剂聚合物提供了增加的生物利用度，从而增加了姜黄素和其代谢物姜黄素O-葡萄糖苷的血浆浓度。姜黄素制药组合物适用于修饰DNA甲基化和治疗癌症等疾病。
• Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof
  申请人：SHIH Charles

  公开号：US20150190351A1

  公开（公告）日：2015-07-09

  The present invention includes compounds, pharmaceuticals and cosmetics having at least one (substituted phenyl)-propenal moiety. The compounds and compositions of the present invention are useful in the treatment or prevention of medical conditions including androgen associated conditions, androgen associated inflammation, a wound (the compounds assist with wound healing), acne, rheumatoid arthritis, psoriasis, rosacea, and alopecia; Kennedy's disease (spinal and bulbar muscular atrophy, or SBMA), polyglutamine-mediated motor neuron degeneration; cancers such as prostate cancer, bladder cancer, breast cancer, ovarian cancer, hepatocellular (liver) cancer, and pancreatic cancer; and other medical conditions described herein. Treatment of such medical conditions includes administering to an individual suffering from a medical condition describe herein, a therapeutically effective amount of any of the disclosed compounds, their derivatives, or pharmaceutical compositions thereof.

  本发明涉及具有至少一个（取代苯基）丙烯醛基团的化合物、药物和化妆品。本发明的化合物和组合物可用于治疗或预防医学状况，包括雄激素相关状况、雄激素相关炎症、创伤（该化合物有助于创伤愈合）、痤疮、类风湿性关节炎、银屑病、酒渣鼻和脱发；肯尼迪病（脊髓和延髓肌肉萎缩症，或SBMA）、多谷氨酸介导的运动神经元退化；癌症，如前列腺癌、膀胱癌、乳腺癌、卵巢癌、肝细胞癌和胰腺癌；以及本文所述的其他医学状况。治疗此类医学状况包括向患有本文所述医学状况的个体施用所述化合物、其衍生物或其药物组成物的治疗有效量。