去甲氧基姜黄素 | 24939-17-1

• 物质功能分类: 有机原料
• 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: 去甲氧基姜黄素
• 中文别名: 脱甲氧姜黄
• 英文名称: 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
• 英文别名: monodemethoxycurcumin；desmethoxycurcumin；demethoxycurcumin；Curcumin II；DMC；1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione；1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• CAS: 24939-17-1
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: HJTVQHVGMGKONQ-UHFFFAOYSA-N

物化性质

• 沸点：
  571.4±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• LogP：
  3.150 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P362+P364,P332+P313
• 危险性描述：
  H315,H319

制备方法与用途

(E/Z)-去甲氧基曲马路那油酮（p-羟基桂皮酰肉桂酸酯）是一种从姜黄属植物中提取的姜黄素，具有抗凝血活性。

反应信息

• 作为反应物：
  描述：

  去甲氧基姜黄素 在 双氧水 作用下， 以 aq. acetate buffer 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  姜黄素降解产物 7-去环戊二酮，由芳基迁移和庚二烯二酮链中的碳损失形成。

  摘要：

  姜黄素的抗炎和其他生物作用可能至少部分是由其代谢物介导的证据强调了识别新型转化产物的重要性。姜黄素在 pH 7.5 缓冲液中的自发降解主要产生双氧化产物，其具有由前庚二烯二酮链的 2 至 6 个碳组成的特征性环戊二酮环。在分析 4'-O-甲基姜黄素的降解反应时，发现产物缺少庚二烯二酮部分的末端碳之一，但含有姜黄素降解产物典型的环戊二酮环和相邻羟基。对姜黄素自氧化反应的分析表明，形成了类似的化合物 7-去环戊二酮，这是一种降解产物，显示出碳的净损失和氧原子的增加。建议通过过氧化物连接的姜黄素二聚体以及自由基介导的愈创木酚部分的 1,2-芳基迁移来去除碳。去甲氧基姜黄素的氧化反应产生去甲氧基-7-去环戊二酮，而从双-去甲氧基姜黄素中没有观察到类似的产物。用姜黄素孵育 RAW264.7 巨噬细胞样细胞显示存在 7-去甲环戊二酮，用 12-O-十四酰佛波醇-13-乙酸酯激活细胞后，7-去甲环戊二酮的形成并未增加。

  DOI：

  10.1021/acs.jnatprod.8b00822

文献信息

• Enzymatic <i>O</i> ‐Prenylation of Diverse Phenolic Compounds by a Permissive <i>O</i> ‐Prenyltransferase from the Medicinal Mushroom <i>Antrodia camphorata</i>
  作者：Junbin He、Zhimin Hu、Zeyuan Dong、Bin Li、Kuan Chen、Zhanpeng Shang、Meng Zhang、Xue Qiao、Min Ye

  DOI：10.1002/adsc.201901396

  日期：2020.2.6

  Prenylated compounds are pharmacologically attractive natural products that are widely distributed in nature. Prenyltransferases (PTs) could catalyze the transfer of prenyl moieties to aromatic acceptors and increase the structural diversity and biological activity of natural products. In this work, a permissive O‐prenyltransferase AcaPT was discovered from Antrodia camphorata, a precious medicinal

  烯丙基化的化合物是在自然界中广泛分布的具有药理吸引力的天然产物。异戊二烯基转移酶（PTs）可以催化异戊二烯基团向芳族受体的转移，并增加天然产物的结构多样性和生物活性。在这项工作中，从台湾珍贵的香菇樟芝中发现了一种允许的邻戊二烯基转移酶AcaPT 。AcaPT对结构多样的药物样酚类化合物（包括Antrodins，类黄酮和香豆素）表现出强大的O-异戊二烯化能力。通过放大酶促合成，总共获得了23种O-异戊烯化产品。AcaPT可用作合成O的有效生物催化剂用于药物开发的异戊二烯基衍生物。
• BETA-AMYLOID AND NEUROFIBRILLARY TANGLE IMAGING AGENTS
  申请人：Mukherjee Jogeshwar

  公开号：US20090004107A1

  公开（公告）日：2009-01-01

  Compounds, compositions and methods are contemplated in which senile plaques and/or neurofibrillary tangles are labeled using compounds with improved permeability across the blood brain barrier and improved selective binding to senile plaques and/or neurofibrillary tangles. Contemplated compounds are derivatives of FDDNP or curcumin, which most preferably have improved solubility in aqueous solvents. Labeling is typically performed using a PET detectable label, and especially 11 C and 18 F.

  考虑到老年斑和/或神经原纤维缠结物的标记，使用具有改进的穿过血脑屏障的渗透性和改进的选择性结合老年斑和/或神经原纤维缠结物的化合物，包括化合物，组合物和方法。考虑到的化合物是FDDNP或姜黄素的衍生物，最好具有在水溶剂中改进的溶解度。标记通常使用PET可检测标记进行，特别是11C和18F。
• Compositions and methods for the treatment of allergic rhinitis
  申请人：Ram Sunder A.N.

  公开号：US20060275516A1

  公开（公告）日：2006-12-07

  The invention concerns novel pharmaceutical compositions and methods for the treatment of allergic rhinitis. More specifically, the invention concerns the inhibition of histamines, which is one of the primary causes of allergic rhinitis in human patients. The inventive pharmaceutical compositions include a carbonyl group-containing moiety, optionally in acidic medium, that combines with histamine to block histamine activity and thus reduce undesirable physiological effects of histamine in the body.

  本发明涉及一种新型药物组合物和治疗过敏性鼻炎的方法。更具体地说，本发明涉及抑制组胺的方法，组胺是人类患者过敏性鼻炎的主要原因之一。该创新性的药物组合物包括含有羰基基团的基团，可选地在酸性介质中，与组胺结合以阻止组胺活性，从而减少组胺在体内的不良生理效应。
• Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases
  申请人：Scaramuzzino, Giovanni

  公开号：EP1336602A1

  公开（公告）日：2003-08-20

  New pharmaceutical compounds of general formula (I): F-(X)q where q is an integer from 1 to 5, preferably 1; -F is chosen among drugs described in the text, -X is chosen among 4 groups -M, -T, -V and -Y as described in the text. The compounds of general formula (I) are nitrate prodrugs which can release nitric oxide in vivo in a controlled and selective way and without hypotensive side effects and for this reason they are useful for the preparation of medicines for prevention and treatment of inflammatory, ischemic, degenerative and proliferative diseases of musculoskeletal, tegumental, respiratory, gastrointestinal, genito-urinary and central nervous systems.

  通式（I）的新药物化合物：F-（X）q，其中q是1到5的整数，最好是1；-F是在文本中描述的药物中选择的，-X是在文本中描述的4个组-M，-T，-V和-Y中选择的。通式（I）的化合物是硝酸盐前药，可以在体内以受控和选择性的方式释放一氧化氮，而不会产生降压副作用，因此它们非常适用于制备用于预防和治疗肌肉骨骼，皮肤，呼吸，消化，泌尿和中枢神经系统的炎症，缺血，退行性和增生性疾病的药物。
• [EN] METAL COMPLEXES OF β-DIKETONES AND/OR POLYPHENOLS BY GREEN CHEMISTRY, PREPARATION METHOD THEREOF, SUNSCREEN THEREOF, SKIN OR HAIR TONE CONCEALER THEREOF, HAIR DYEING THEREOF AND OTHER USES THEREOF<br/>[FR] COMPLEXES MÉTALLIQUES DE β-DICÉTONES ET/OU DE POLYPHÉNOLS PAR CHIMIE VERTE, PROCÉDÉ DE PRÉPARATION, ÉCRAN SOLAIRE, CORRECTEUR DE TEINT DE LA PEAU OU DES CHEVEUX, TEINTURE CAPILLAIRE ET UTILISATIONS ASSOCIÉS
  申请人：RAMIREZ RIOS LILIANA PATRICIA

  公开号：WO2019238261A1

  公开（公告）日：2019-12-19

  The present invention relates to a method to synthesize with high yield a colored metal complex of β-diketones and/or polyphenols by mechanochemistry without using aqueous or organic solvents and covers new complexes obtained therefrom. In an embodiment, only the reactants, a metal alkoxide and a β-diketone and/or a polyphenol, are present and react at different molar ratios to form a metal complex in the form of a homogeneous colored material (i.e. powder) with high yield. If curcumin is used, the color of the final metal complex dye depends on several factors such as the curcuminoids, the metal, the type of alkoxide used, the stoichiometric molar ratio of both reactants and the additives used. If titanium alkoxide and any additive is used, a red or violet colored titanium curcumin complex in powder form is produced. The production process of the metal complex in powder form is characterized by facility of scale up. The entire product is ready to be used in several applications. If polyphenols such as ferulic acid, quercetin, ellagic acid or lignin are used instead of curcumin, other colored complexes are obtained using mechanochemistry. In addition, the product comprising metal complexes of β-diketones and/or polyphenols is characterized by green chemistry manufacture. Besides, these metal complexes of β-diketones and/or polyphenols in several formulations are characterized by improved stability under storage conditions and improved sun protection against UV rays for human skin and human hair. The product is ready to be used alone or in combination with other additives or active ingredients in different formulations. The invention also covers the use of these metal β-diketones/polyphenol complexes in food, cosmetics, the pharmaceutical field and in the creativity field, as sunscreen, skin and hair concealer or foundation in powder form or cream, keratinous dye, textile dye, food dye, dye emulsions, miniemulsions, polymer colloids and catalysts. The production process of these novel metal-complex dyes is also characterized by rapid production of colored compounds without using solvents and, thus, ecofriendliness. The process of the production of metal β-diketone and/or polyphenol complexes is characterized by the non-formation of toxic by-products and high yield. In addition, the present invention comprises a hair dyeing molecule or formulation and procedure combining excellent dyeing properties with reduced risk of development cancer or allergies, while being ecological and of the natural origin.

  本发明涉及一种通过机械化学合成β-二酮和/或多酚的有色金属络合物的方法，不使用水或有机溶剂，并涵盖从中获得的新络合物。在一种实施方式中，只有反应物，金属烷氧基和β-二酮和/或多酚存在，并以不同的摩尔比反应形成均匀有色材料（即粉末）的金属络合物，收率高。如果使用姜黄素，则最终金属络合物染料的颜色取决于多种因素，例如姜黄素，金属，使用的烷氧基类型，两种反应物的化学计量比以及使用的添加剂。如果使用钛烷氧基和任何添加剂，则会产生红色或紫色的钛姜黄素复合物粉末。金属络合物的粉末形式的生产过程具有易于扩大规模的特点。整个产品已准备好用于多种应用。如果使用多酚，例如ferulic酸，quercetin，ellagic酸或lignin代替姜黄素，则使用机械化学合成获得其他有色络合物。此外，由β-二酮和/或多酚的金属络合物组成的产品具有绿色化学制造的特点。此外，这些β-二酮和/或多酚的金属络合物在多种配方中具有改善的稳定性和对人体皮肤和头发的紫外线防护性能。该产品已准备好单独或与其他添加剂或活性成分组合在不同的配方中使用。本发明还涵盖在食品，化妆品，制药领域和创意领域中使用这些金属β-二酮/多酚络合物，作为防晒剂，皮肤和头发遮瑕膏或粉底，角蛋白染料，纺织染料，食品染料，染料乳液，微乳液，聚合物胶体和催化剂。这些新型金属络合染料的生产过程也具有快速生产有色化合物而不使用溶剂的特点，因此具有环保性。金属β-二酮和/或多酚络合物的生产过程的特点是不会形成有毒副产物和高收率。此外，本发明还包括一种头发染料分子或配方和程序，将优异的染色性能与降低癌症或过敏风险相结合，同时具有生态和天然的特点。