alpha,3,4-三羟基-苯丙酸; 丹参素乳酸 | 23028-17-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: alpha,3,4-三羟基-苯丙酸; 丹参素乳酸
• 中文别名: 丹参素乳酸；alpha,3,4-三羟基-苯丙酸;丹参素乳酸；ALPHA,3,4-三羟基-苯丙酸；丹参素
• 英文名称: danshensu
• 英文别名: salvianic acid A；3-(3,4-dihydroxyphenyl)lactic acid；3,4-dihydroxyphenyllactic acid；tanshinol；salvianic acid；2-hydroxy-3-(3,4-dihydroxyphenyl)propanoic acid；β-(3,4-dihydroxyphenyl)lactic acid；α-hydroxyhydrocaffeic acid；DOPL；3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid
• CAS: 23028-17-3
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: PAFLSMZLRSPALU-UHFFFAOYSA-N

物化性质

• 沸点：
  481.5±40.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3 (20 ºC 760 Torr)
• LogP：
  0.045 (est)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2918290000

制备方法与用途

丹参酸A（也称为（Rac）-丹参素），是一种酚酸，能有效清除自由基并具有抗氧化作用。

反应信息

• 作为反应物：
  描述：

  alpha,3,4-三羟基-苯丙酸; 丹参素乳酸 在 氢氧化钾 、 乙醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 65.0h， 生成 3-(3,4-Bis-allyloxy-phenyl)-2-hydroxy-propionic acid allyl ester
  参考文献：
  名称：

  Bryophyte Constituents; 7: New Synthesis of (+)-Rosmarinic Acid and Related Compounds

  摘要：

  描述了迷迭香酸（1）及其衍生物2-4的高效快捷合成方法，广泛采用了烯丙基保护基团用于羧酸和酚类构建单元。通过化学酶促拆分其苯基乳酸前体，获得了(+)-(R)-迷迭香酸。

  DOI：

  10.1055/s-1996-4289
• 作为产物：
  描述：

  (Z)-2-acetamido-3-(3,4-diacetoxyphenyl)acrylic acid 在 盐酸 、 水 、 氢气 作用下， 以 乙醇 为溶剂， 60.0~100.0 ℃ 、1.0 MPa 条件下， 反应 22.0h， 生成 alpha,3,4-三羟基-苯丙酸; 丹参素乳酸
  参考文献：
  名称：

  Improved Process for Pilot-Scale Synthesis of Danshensu ((±)-DSS) and Its Enantiomer Derivatives

  摘要：

  A pilot-scale process has been developed for green and scalable synthesis of (+/-)-beta-(3,4-dihydroxyphenyl) lactic acid ((+/-)-DSS) and their two important derivatives, namely, (+/-)-IDHP [(+/-)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (+/-)-DBZ [(+/-)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (+/-)-DBZ and 49.2% for (+/-)-IDHP compared to the initial process with a yield of 12% for (+/-)-DBZ and 18% for (+/-)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(-)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(-)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).

  DOI：

  10.1021/op4002593

文献信息

• A Modified Synthesis of (±)-β-Aryllactic acids
  作者：Henry N. C. Wong、Zun Le Xu、Hson Mou Chang、Chi Ming Lee

  DOI：10.1055/s-1992-26228

  日期：——

  The synthesis of racemic forms of the reportedly active principle of Danshen, namely (±)-ß-(3,4-dihydroxyphenyl)lactic acid [(±)- 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid] and its seven racemic derivatives is reported.

  据报道，丹参中活性成分的外消旋形式，即（±）-ß-(3,4-二羟基苯基)乳酸[(±)-3-(3,4-二羟基苯基)-2-羟基丙酸]及其七种外消旋衍生物已成功合成。
• Methods for treating of skin conditions with retinoid double conjugate compounds
  申请人：US COSMECEUTECHS LLC

  公开号：US10123960B2

  公开（公告）日：2018-11-13

  A double conjugate molecule made of a retinoid, an organic acid, particularly an a-hydroxy acid, and an alcohol or acyl group, is provided which is useful in treating skin conditions, particularly aging. The retinoid, organic acid, and alcohol/acyl group are preferably linked via ester bonds.

  提供一种由视黄醇、有机酸（特别是α-羟基酸）和醇或酰基组成的双共轭分子，可用于治疗皮肤状况，特别是衰老。视黄醇、有机酸和醇/酰基组最好通过酯键连接。
• Synthesis and photophysics of novel biocompatible fluorescent oxocines and azocines in aqueous solution
  作者：A. Ulises Acuña、Mónica Álvarez-Pérez、Marta Liras、Pedro B. Coto、Francisco Amat-Guerri

  DOI：10.1039/c3cp52228h

  日期：——

  accompanying monardine ionization which may abolish de-excitation via intersystem crossing. A similar fluorogenic reaction takes place with catecholamines such as dopamine and DOPA, to yield fluorescent azocines 2a and 2b which, depending on pH, may be present as cationic, neutral or anionic species. TDDFT computations of these forms were also carried out to assign the corresponding excitation transitions

  不同质子形式的强荧光半缩醛4,9-二羟基-1,2-二氢-4,11a-甲氧羰基[4,5 - b ]苯并呋喃-5（4 H）-（1a，莫纳ardine），氮杂类似物4，9-二羟基-3，4-二氢-1 H -4，11a-甲基苯并呋喃[2，3 - d ]偶氮素-5（2 H）-1（2a，氮莫尼丁）和各自的2-羧基衍生物（1b，2b）已通过实验和量子化学方法进行了研究。莫纳丁和羧莫纳丁分别是水溶液中羟基酪醇或丹酚酸的新型荧光室温反应的主要产物，它们具有独特的光物理性质。接近中性pH（p K a = 7.2）的黄嘌呤从弱发射，吸收紫外线的（382 nm）中性物质切换为吸收VIS（426 nm），发射蓝光（464 nm）的阴离子形式，并具有荧光量子产率φ ˚F = 1和单指数衰减τ ˚F= 2.74 ns。基于时间相关的密度泛函理论（TDDFT）计算，解释了这种从中性到阴离子形式的二元光谱变化，这是由于（i）
• Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives
  申请人：Auriol Daniel

  公开号：US20090233876A1

  公开（公告）日：2009-09-17

  The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5). These O-α-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhythmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application.

  该发明涉及通过酶催化将选择自间苯二酚或其衍生物的酚类与蔗糖的葡萄糖部分进行缩合来制备酚类衍生物。所述酚类衍生物的生产是通过葡萄糖转移酶（EC 2.4.1.5）实现的。所选酚类的这些O-α-葡糖苷是新的，其在水中的溶解度高于它们的原始多酚，并且在化妆品和药用组合物中具有有用的应用，如抗氧化、抗病毒、抗菌、免疫刺激、抗过敏、降压、抗缺血、抗心律失常、抗血栓形成、降胆固醇、抗脂质过氧化、肝脏保护、抗炎症、抗癌变突变、抗肿瘤、抗血栓形成和扩血管等配方，或者在任何其他应用领域中。
• Synthesis and activity towards Alzheimer's disease in vitro: Tacrine, phenolic acid and ligustrazine hybrids
  作者：Guoliang Li、Ge Hong、Xinyu Li、Yan Zhang、Zengping Xu、Lina Mao、Xizeng Feng、Tianjun Liu

  DOI：10.1016/j.ejmech.2018.01.028

  日期：2018.3

  and screened as novel potential anti-Alzheimer drug candidates. These compounds showed potent inhibition activity towards cholinesterases (ChEs), among of them, 9i was the most potent one towards acetylcholinesterase (eeAChE, IC50 = 3.9 nM; hAChE, IC50 = 65.2 nM). 9i could also effectively block β-amyloid (Aβ) self-aggregation with an inhibition ratio of 47% at 20 μM. In addition, its strong anti-oxidation

  合成了一系列新颖的他克林-酚酸二杂合物和他克林-酚酸-木二嗪三杂合物，表征并筛选为新型潜在的抗阿尔茨海默氏症候选药物。这些化合物显示出对胆碱酯酶（ChEs）的有效抑制活性，其中9i是对乙酰胆碱酯酶最有效的抑制因子（ee AChE，IC 50  = 3.9 nM；h AChE，IC 50  = 65.2 nM）。9i还可以有效地阻止β-淀粉样蛋白（Aβ）的自聚集，在20μM时的抑制率为47％。此外，其强大的抗氧化活性可以保护PC12细胞免受CoCl 2的影响-在实验条件下受损，而没有神经毒性。此外，其肝毒性在体外和体内均低于他克林。动力学和分子建模研究表明，9i以混合类型工作，可以同时与AChE的催化活性位点（CAS）和外围阴离子位点（PAS）相互作用。因此，9i是用于治疗AD的有希望的多功能候选药物。