(R)-3-(4-羟苯基)乳酸 | 89919-57-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (R)-3-(4-羟苯基)乳酸
• 中文别名: (2S)-3-(4-羟基苯基)2-羟基丙酸；(R)-2-羟基-3-(4-羟基苯基)丙酸
• 英文名称: (R)-3-(4-hydroxyphenyl)lactic acid
• 英文别名: (R)-2-hydroxy-3-(4-hydroxyphenyl)propanoic acid；D-Hpla；β-(4-hydroxyphenyl) lactic acid；(2R)-2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
• CAS: 89919-57-3
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: JVGVDSSUAVXRDY-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2918290000

反应信息

• 作为反应物：
  描述：

  (R)-3-(4-羟苯基)乳酸 在 4-二甲氨基吡啶 、 硫酸 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Latifolicinin A from a Fermented Soymilk Product and the Structure–Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth

  摘要：

  The functional components in soymilk may vary depending upon the fermentation process. A fermented soymilk product (FSP) obtained by incubation with the microorganisms of intestinal microflora was found to reduce the risk of breast cancer. Guided by the inhibitory activities against breast cancer cells, two cytotoxic compounds, daidzein and (S)-latifolicinin A, were isolated from the FSP by repetitive extraction and chromatography. Latifolicinin A is the n-butyl ester of beta-(4-hydroxyphenyl)lactic acid (HPLA). A series of the ester and amide derivatives of (S)-HPLA and L-tyrosine were synthesized for evaluation of their cytotoxic activities. In comparison, (S)-HPLA derivatives exhibited equal or superior inhibitory activities to their L-tyrosine counterparts, and (S)-HPLA amides showed better cytotoxic activities than their corresponding esters. In particular, (S)-HPLA farnesyl amide was active to triple-negative MDA-MB-231 breast cancer cells (IC50 = 27 mu M) and 10-fold less toxic to Detroit-551 normal cells.

  DOI：

  10.1021/acs.jafc.5b04028
• 作为产物：
  描述：

  DL-酪氨酸 生成 (R)-3-(4-羟苯基)乳酸
  参考文献：
  名称：

  Tsudji, Acta Scholae Medicinalis Universitatis in Kioto, 1917, vol. 1, p. 443

  摘要：

  DOI：

文献信息

• Enantioselective synthesis of α-hydroxy carboxylic acids: Direct conversion of α-oxocarboxylic acids to enantiomerically enriched α-hydroxy carboxylic acids via neighboring group control
  作者：Zhe Wang、Brittany La、Joseph M. Fortunak、Xian-Jun Meng、George W. Kabalka

  DOI：10.1016/s0040-4039(98)01162-9

  日期：1998.7

  α-Oxocarboxylic acids can be reduced to the corresponding α-hydroxy carboxylic acids employing DIP-C1tm as a reducing agent. The α-carboxylic substituent exerts a remarkable neighboring group effect on the reduction. The reaction presumably proceeds in an intramolecular fashion through a “rigid” bicyclic transition state assembly, which produces enantioselectivities approaching 99%.

  可以使用DIP-C1 tm作为还原剂将α-氧代羧酸还原为相应的α-羟基羧酸。α-羧基取代基对还原反应具有显着的邻近基团效应。该反应大概通过“刚性”双环过渡态组装体以分子内方式进行，其产生接近99％的对映选择性。
• Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
  作者：Naoyuki Shimada、Naoya Takahashi、Naoki Ohse、Masayoshi Koshizuka、Kazuishi Makino

  DOI：10.1039/d0cc05630h

  日期：——

  The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B

  描述了使用二硼酸酐酸酐催化剂使用羧酸的催化羟基直接脱水酰胺化直接合成Weinreb酰胺的第一个成功实例。该方法适用于八种α-羟基酮天然产物的简明合成，它们分别为司塔巴星，4-羟基司他巴星，库拉索菌素A和B，茄型酚A和B以及环丁香素B和C。
• MICROORGANISMS AND METHODS FOR PRODUCTION OF 4-HYDROXYBUTYRATE, 1,4-BUTANEDIOL AND RELATED COMPOUNDS
  申请人：Genomatica, Inc.

  公开号：US20150148513A1

  公开（公告）日：2015-05-28

  The invention provides non-naturally occurring microbial organisms having a 4-hydroxybutyrate, 1,4-butanediol, or other product pathway and being capable of producing 4-hydroxybutyrate, 1,4-butanediol, or other product, wherein the microbial organism comprises one or more genetic modifications. The invention additionally provides methods of producing 4-hydroxybutyrate, 1,4-butanediol, or other product or related products using the microbial organisms.

  该发明提供了具有4-羟基丁酸、1,4-丁二醇或其他产物途径并能够产生4-羟基丁酸、1,4-丁二醇或其他产物的非自然微生物生物体，其中该微生物生物体包括一个或多个基因修饰。该发明还提供了利用这些微生物生物体生产4-羟基丁酸、1,4-丁二醇或其他产物或相关产品的方法。
• Biocontrolled Formal Inversion or Retention of<scp>L</scp>-α-Amino Acids to Enantiopure (<i>R</i>)- or (<i>S</i>)-Hydroxyacids
  作者：Eduardo Busto、Nina Richter、Barbara Grischek、Wolfgang Kroutil

  DOI：10.1002/chem.201403195

  日期：2014.8.25

  Natural L‐α‐amino acids and L‐norleucine were transformed to the corresponding α‐hydroxy acids by formal biocatalytic inversion or retention of absolute configuration. The one‐pot transformation was achieved by a concurrent oxidation reduction cascade in aqueous media. A representative panel of enantiopure (R)‐ and (S)‐2‐hydroxy acids possessing aliphatic, aromatic and heteroaromatic moieties were

  天然的L -α-氨基酸和L-正亮氨酸通过正式的生物催化转化或保留绝对构型而转化为相应的α-羟基酸。通过在水性介质中同时进行氧化还原级联反应来实现单锅转化。具有高分离度（67–85％）和对映纯形式（> 99％ee）的高分离度分离了具有脂肪族，芳香族和杂芳族部分的对映体（R）-和（S）-2-羟基酸的代表小组，而无需进行色谱纯化。
• [EN] AMIDE LINKER PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RECEPTEUR ACTIVE DE LA PROLIFERATION DES PEROXISOMES A LIEUR AMIDE
  申请人：LILLY CO ELI

  公开号：WO2004000789A1

  公开（公告）日：2003-12-31

  The present invention is directed to compounds, compositions, and use of compounds the structural Formula (I).

  本发明涉及结构式(I)的化合物、组合物及其使用。