trans-Arachidin 3 | 87320-15-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-Arachidin 3
• 英文别名: trans-4-(3-methyl-1-butenyl)-3,5,4'-trihydroxystilbene；trans-arachidin-3；arachidin-3；arachidin III；5-[(E)-2-(4-hydroxyphenyl)ethenyl]-2-[(E)-3-methylbut-1-enyl]benzene-1,3-diol
• CAS: 87320-15-8
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: XTDKVQYWANHUFS-RUQOPNIZSA-N

物化性质

• 沸点：
  494.6±14.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  diethyl (4-((triisopropylsilyl)oxy)benzyl)phosphonate 在 盐酸 、 potassium tert-butylate 、 四丁基氟化铵 、 水 、 ethylenediamine Tetraacetic Acid 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 25.0h， 生成 trans-Arachidin 3
  参考文献：
  名称：

  从花生种子中总合成Chiricanine A，Arahypin-1，反-Arachidin-2，反-Arachidin-3和Arahypin-5

  摘要：

  天然的异戊烯基斯蒂芬斯鸟氨酸A（2），arahypin-1（3），trans -arachidin-2（4），trans -arachidin-3（5）和arahypin-5（6）的首次合成。描述。2和3的合成是通过聚合序列或从pinosylvin开始的一步反应完成的。的合成4，5和6是从（实现Ë）-3,5-双-甲氧基甲基-4'-三异丙基甲硅烷基氧基sti通过具有双甲氧基甲基醚基的苯甲醛与具有三异丙基甲硅烷基氧基的苄基膦酸酯之间的霍纳-沃兹沃思-埃蒙斯反应获得。

  DOI：

  10.1021/np100696f

文献信息

• Compositions and methods of synthesizing arachidin-3 from resveratrol
  申请人：Parnative, Inc.

  公开号：US09981895B1

  公开（公告）日：2018-05-29

  Composition, methods of synthesizing trans-arachidin-3; and, methods of use as a dietary supplement, food additive, pharmaceutical, nutraceutical, cosmeceutical, and antioxidant. The methods of production entail organic syntheses using primary alkylamines or primary hydroxyalkyl amines, or carboxy amines (amino acids) with natural carboxylic acids (acetic acid) as catalysts to react isovaleraldehye with trans-resveratrol. The synthesis is carried out in organic solvent, which is composed of an azeotropic mixture comprising toluene with pyridine, n-butanol, n-propanol, 2-propanol, 2-methyl-1-propanol, or other alcohols that form an azeotrope with toluene. The final product is purified and analyzed for the amount of trans-arachidin-3, such as via HPLC, IR, column chromatography, and high-performance counter-current chromatography. All solvent and catalysts used in the reaction are approved by the FDA as either food additives, secondary direct food additives, and/or indirect food additives, and thus this synthetic trans-arachidin-3 may be used in the food and cosmetic industry.

  合成反式花生酸-3的方法；以及作为膳食补充剂、食品添加剂、药物、营养保健品、化妆品和抗氧化剂的使用方法。生产方法涉及使用一次性烷基胺或一次性羟基烷基胺或羧基胺(氨基酸)与天然羧酸(乙酸)作为催化剂，使异戊醛与反式白藜芦醇反应。合成在有机溶剂中进行，该溶剂由甲苯与吡啶、正丁醇、丙醇、2-丙醇、2-甲基-1-丙醇或其他与甲苯形成共沸混合物的醇组成。最终产品经过纯化和分析，例如通过HPLC、IR、柱层析和高效逆流色谱法检测反式花生酸-3的含量。在反应中使用的所有溶剂和催化剂均获得FDA批准，作为食品添加剂、间接食品添加剂或直接食品添加剂，因此这种合成的反式花生酸-3可以在食品和化妆品行业中使用。
• CHEMICAL DERIVATIVES AND METHODS FOR SYNTHESIZING AND COMPOUNDING CHEMICAL DERIVATIVES RELATED TO CAPSAICIN PALMITATE AND CAPSAICIN PRODRUGS
  申请人：Chorda Pharma, Inc.

  公开号：US20220168259A1

  公开（公告）日：2022-06-02

  Capsaicin compositions and methods for enhancing hydrophobicity of a molecule useful for pharmaceutical applications, including: (1) a prodrug using a linker such as a carbamate between capsaicin with other structures in order to optimize kinetic control of capsaicin cleavage; (2) a prodrug using a linker such as an unsaturated carboxylic ester between capsaicin with other structures in order to optimize kinetic control of capsaicin cleavage; (3) esters of long-chain fatty acids and capsaicin where hydroxyl groups provide handles for attachment of additional capsaicin molecules; and (4) the use of carboxylic acid diesters to increase overall hydrophobicity of two or more covalently-linked capsaicin molecules. Formulations of palmitated esters of capsaicin are also described, which are designed to enhance hydrophobicity of a molecule useful for pharmaceutical applications, for example to provide compounded mixtures designed to optimize analgesic efficacy.
• US9981895B1
  申请人：——

  公开号：US9981895B1

  公开（公告）日：2018-05-29
• Total Synthesis of Chiricanine A, Arahypin-1, <i>trans</i>-Arachidin-2, <i>trans</i>-Arachidin-3, and Arahypin-5 from Peanut Seeds
  作者：Byung Ho Park、Hee Jin Lee、Yong Rok Lee

  DOI：10.1021/np100696f

  日期：2011.4.25

  The first and efficient syntheses of the naturally occurring prenylated stilbenes chiricanine A (2), arahypin-1 (3), trans-arachidin-2 (4), trans-arachidin-3 (5), and arahypin-5 (6) are described. Syntheses of 2 and 3 were accomplished by either a convergent sequence or a one-step reaction starting from pinosylvin. Syntheses of 4, 5, and 6 were achieved from (E)-3,5-bis-methoxymethyl-4′-triisopropylsilyloxystilbene

  天然的异戊烯基斯蒂芬斯鸟氨酸A（2），arahypin-1（3），trans -arachidin-2（4），trans -arachidin-3（5）和arahypin-5（6）的首次合成。描述。2和3的合成是通过聚合序列或从pinosylvin开始的一步反应完成的。的合成4，5和6是从（实现Ë）-3,5-双-甲氧基甲基-4'-三异丙基甲硅烷基氧基sti通过具有双甲氧基甲基醚基的苯甲醛与具有三异丙基甲硅烷基氧基的苄基膦酸酯之间的霍纳-沃兹沃思-埃蒙斯反应获得。