((+)-(R)-(Z,Z)-1-(acetyloxy)-2-hydroxy-12,15-heneicosadien-4-one) | 56164-07-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ((+)-(R)-(Z,Z)-1-(acetyloxy)-2-hydroxy-12,15-heneicosadien-4-one)
• 英文别名: (+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl acetate；(2R,12Z,15Z)-1-acetoxy-2-hydroxy-4-oxoheneicosa-12,15-diene；(R,12Z,15Z)-1-acetoxy-2-hydroxy-4-oxo-heneicosa-12,15-diene；(2R,12Z,15Z)-2-hydroxy-4-oxoheneicosa-12,15-dienyl acetate；(R,12Z,15Z)-2-hydroxy-4-oxo-henicosa-12,15-dienyl acetate；(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate；Persin；[(2R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl] acetate
• CAS: 56164-07-9
• 化学式: C₂₃H₄₀O₄
• 分子量: 380.568
• InChiKey: IBDVBNUJEGRVQN-RHNLGMIQSA-N

物化性质

• 沸点：
  504.5±50.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((+)-(R)-(Z,Z)-1-(acetyloxy)-2-hydroxy-12,15-heneicosadien-4-one) 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 以50%的产率得到(R)-2-hydroxy-4-oxo-henicosan-1-yl acetate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells

  摘要：

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.006
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 32.67h， 生成 ((+)-(R)-(Z,Z)-1-(acetyloxy)-2-hydroxy-12,15-heneicosadien-4-one)
  参考文献：
  名称：

  Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells

  摘要：

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.006

文献信息

• Antimicrobial, antibacterial and spore germination inhibiting activity from an avocado extract enriched in bioactive compounds
  申请人：Instituto Tecnologico Y De Estudios Superiores De Monterrey

  公开号：EP2851062A2

  公开（公告）日：2015-03-25

  The present invention relates to extracts from Persea sp. (avocado) enriched in bioactive compounds which can be used as antimicrobial, antibacterial or spore germination inhibiting agents, the process for obtaining the extracts, acetogenins and isolated molecules and methods for using the extracts enriched in bioactive compounds for providing antimicrobial, antibacterial or spore germination inhibiting effect.

  本发明涉及富含生物活性化合物（可用作抗菌剂、抑菌剂或孢子发芽抑制剂）的牛油果（Persea sp.）萃取物、获取萃取物、乙酰皂苷元和分离分子的工艺，以及使用富含生物活性化合物的萃取物提供抗菌剂、抑菌剂或孢子发芽抑制效果的方法。
• Inhibitory activity of acetogenins against Listeria monocytogenes
  申请人：INSTITUTO TECHNOLOGICO Y DE ESTUDIOS SUPERIORES DE MONTERREY

  公开号：US10932484B2

  公开（公告）日：2021-03-02

  One aspect of the present invention relates to a method of inhibiting growth of Listeria monocytogenes on or in a product by applying an inhibitor compound of the formula: where the dashed lines are optional and represent a double bond or triple bond, and at least one of the dashed lines is present. Also disclosed is a method of inhibiting growth of Listeria monocytogenes on or in a subject by treating the subject with that compound. Further aspects of the present invention relate to pharmaceutical compositions, food product compositions, personal care product compositions, and cleaning product compositions comprising the subject inhibitor compounds.

  本发明的一个方面涉及一种通过使用式中的抑制剂化合物来抑制产品上或产品中李斯特菌生长的方法： 其中虚线是可选的，代表双键或三键，且至少有一条虚线存在。还公开了一种通过用该化合物处理受试者来抑制受试者身上或体内李斯特菌生长的方法。本发明的其它方面涉及包含所述抑制剂化合物的药物组合物、食品组合物、个人护理产品组合物和清洁产品组合物。
• Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons
  作者：De Run Li、Andiappan Murugan、J. R. Falck

  DOI：10.1021/ja076802c

  日期：2008.1.1

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
• ANTIMICROBIAL, ANTIBACTERIAL AND SPORE GERMINATION INHIBITING ACTIVITY FROM AN AVOCADO EXTRACT ENRICHED IN BIOACTIVE COMPOUNDS
  申请人：ESTUDIOS SUPERIORES DE MONTERREY INSTITUTO TECNOLOGICO Y DE

  公开号：US20130216488A1

  公开（公告）日：2013-08-22

  The present disclosure relates to extracts from Persea sp. (avocado) enriched in bioactive compounds which can be used as antimicrobial, antibacterial or spore germination inhibiting agents, the process for obtaining the extracts, acetogenins and isolated molecules and methods for using the extracts enriched in bioactive compounds for providing antimicrobial, antibacterial or spore germination inhibiting effect.
• ANTIMICROBIAL ANTIBACTERIAL AND SPORE GERMINATION INHIBITING ACTIVITY FROM AN AVOCADO EXTRACT ENRICHED IN BIOACTIVE COMPOUNDS
  申请人：INSTITUTO TECNOLOGICO Y DE ESTUDIOS SUPERIORES DE MONTERREY

  公开号：US20170055526A1

  公开（公告）日：2017-03-02

  The present disclosure relates to extracts from Persea sp. (avocado) enriched in bioactive compounds which can be used as antimicrobial, antibacterial or spore germination inhibiting agents, the process for obtaining the extracts, acetogenins and isolated molecules and methods for using the extracts enriched in bioactive compounds for providing antimicrobial, antibacterial or spore germination inhibiting effect.