(2E,4E,6E,8E,10E)-dodeca-2,4,6,8,10-pentaenal | 80123-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4E,6E,8E,10E)-dodeca-2,4,6,8,10-pentaenal
• 英文别名: 2,4,6,8,10,12-dodeca-pentaenal；2,4,6,8,10-dodecapentaenal；(all-E)-dodeca-2,4,6,8,10-pentaenal；dodeca-2t,4t,6t,8t,10t-pentaenal
• CAS: 80123-48-4
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: NLPJEWTYXLOFLM-GNUNTXLASA-N

物化性质

• 熔点：
  166 °C
• 沸点：
  110-140 °C(Press: 0.2 Torr)
• 密度：
  0.907±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,4E,6E,8E,10E)-dodeca-2,4,6,8,10-pentaenal 在 Acetobacter aceti MIM₂₀₀₀/28 作用下， 以 phosphate buffer 、 乙醇 为溶剂， 反应 48.0h， 以65%的产率得到all(E)-2,4,6,8,10-dodecapentaenoic acid
  参考文献：
  名称：

  醋酸醋杆菌将多共轭化合物直接转化为其相应的羧酸

  摘要：

  使用醋酸醋杆菌（Acetobacter aceti）将多共轭醛或醇转化为相应的酸。将分析结果与使用霍纳-维蒂希反应化学获得的酸进行了比较。

  DOI：

  10.1016/j.tet.2008.07.011
• 作为产物：
  描述：

  (2E)-5,5-dimethoxypent-2-enal 在 potassium tert-butylate 、 氢溴酸 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 、 正戊烷 为溶剂， 反应 2.0h， 生成 (2E,4E,6E,8E,10E)-dodeca-2,4,6,8,10-pentaenal
  参考文献：
  名称：

  功能化的乙烯基有机锂化合物，ω-硫代山梨醇醛的合成当量

  摘要：

  官能乙烯基阴离子和与醛和酮水解为多烯醛之后导致反应。它们已用于合成navenoneB 。

  DOI：

  10.1016/s0040-4039(00)70701-5

文献信息

• Products of the iterative polyketide synthases in 9- and 10-membered enediyne biosynthesis
  作者：Huihua Sun、Rong Kong、Di Zhu、Min Lu、Qiang Ji、Chong Wai Liew、Julien Lescar、Guofu Zhong、Zhao-Xun Liang

  DOI：10.1039/b916751j

  日期：——

  The iterative polyketide synthases from the biosynthetic pathways of three enediyne natural products were examined. The results established the all-trans conjugated pentadecaheptanene as the only major product shared by the PKSs. The experiments further revealed some intrinsic differences among the PKSs by demonstrating the formation of different by-products.

  研究了三种烯二炔天然产物的生物合成途径中的迭代聚酮化合物合酶。结果确定了全反式共轭十五碳烯是PKS共享的唯一主要产物。通过证明形成不同的副产物，实验进一步揭示了PKS之间的某些内在差异。
• [EN] POLYUNSATURATED LINEAR ALDEHYDES AND THEIR DERIVATIVES WITH ANTI-RADICAL AND ANTI-TUMORAL ACTIVITY<br/>[FR] ALDEHYDES LINEAIRES POLYINSATURES ET LEURS DERIVES A ACTIVITE ANTI-RADICALAIRE ET ANTI-TUMORALE
  申请人：UNIV DEGLI STUDI MILANO

  公开号：WO2003095403A1

  公开（公告）日：2003-11-20

  The invention relates to polyunsaturated linear aldehydes and derivatives thereof which can be extracted from the feathers or tissues of parrots of prepared synthetically with antioxidant, antitumoral and anti-inflammatory activity, and which are useful in the prevention and treatment of cardiovascular, inflammatory, atherosclerotic, proliferative cell and tumour damage and the prevention of alterations caused by ageing.

  本发明涉及从鹦鹉的羽毛或组织中提取或通过合成制备的多不饱和线性醛及其衍生物，具有抗氧化、抗肿瘤和抗炎活性，并可用于预防和治疗心血管、炎症、动脉粥样硬化、增生细胞和肿瘤损伤以及预防衰老引起的变化。
• Process for the preparation of 2,4,6-octatriene-1-oic acid and 2,4,6-octatriene-1-ol
  申请人：Giuliani S.p.A.

  公开号：EP2241543A1

  公开（公告）日：2010-10-20

  The present invention concerns a process for synthesis of 2,4,6-octatriene-1-oic acid and 2,4,6-octatriene-1-ol, which comprises the following stages: a) reaction between 2,4-trans-hexadienal and triethyl phosphonoacetate to give ethyl 2,4,6-trans-octatrienoate; b) alkaline hydrolysis of ethyl 2,4,6-trans-octatrienoate to give the corresponding alkaline salt; c) acidification of said salt to give 2,4,6-trans-octatrienoic acid, which can be separated or can undergo the following further stages: d) reaction of the 2,4,6-trans-octatrienoic acid with ethyl chloroformiate to give the mixed anhydride formed by 2,4,6-trans-octatrienoic acid and ethyl carbonic acid; e) reduction of said mixed anhydride with sodium borohydride to give 2,4,6-transoctatrienol; and optionally a purification stage of the end product.

  本发明涉及一种合成2,4,6-辛三烯-1-酸和2,4,6-辛三烯-1-醇的方法，包括以下步骤：a) 2,4-顺-己二烯和三乙基磷酸乙酯反应，得到乙酸2,4,6-顺-辛三烯酯；b) 碱性水解乙酸2,4,6-顺-辛三烯酯，得到相应的碱性盐；c) 酸化上述盐，得到2,4,6-顺-辛三烯酸，可以分离或可以经历以下进一步步骤：d) 2,4,6-顺-辛三烯酸与氯乙酸乙酯反应，得到由2,4,6-顺-辛三烯酸和乙酸乙酯形成的混合酐；e) 用硼氢化钠还原该混合酐，得到2,4,6-顺-辛三烯醇；以及可选的最终产物纯化阶段。
• Polyunsaturated linear aldehydes and their derivatives with anti-radical and anti-tumoral activity
  申请人：Stradi Riccardo

  公开号：US20050175555A1

  公开（公告）日：2005-08-11

  The invention relates to polyunsaturated linear aldehydes and derivatives thereof which can be extracted from the feathers or tissues of parrots of prepared synthetically with antioxidant, antitumoral and anti-inflammatory activity, and which are useful in the prevention and treatment of cardiovascular, inflammatory, atherosclerotic, proliferative cell and tumour damage and the prevention of alterations caused by ageing.

  本发明涉及从鹦鹉的羽毛或组织中提取或合成的多不饱和线性醛及其衍生物，具有抗氧化、抗肿瘤和抗炎活性，可用于预防和治疗心血管、炎症性、动脉粥样硬化、增殖细胞和肿瘤损伤以及预防衰老引起的变化。
• Investigation of a Mechanism for Accelerated Breakdown of Immune Tolerance to the Primary Biliary Cirrhosis–Associated Autoantigen, Pyruvate Dehydrogenase Complex
  作者：David E J Jones、Jeremy M Palmer、Kate Bennett、Amanda J Robe、Stephen J Yeaman、Helen Robertson、Margaret F Bassendine、Alastair D Burt、John A Kirby

  DOI：10.1038/labinvest.3780413

  日期：2002.2

  Primary biliary cirrhosis (PBC) is an autoimmune liver disease characterized by autoreactive T- and B-cell responses to the highly conserved enzyme pyruvate dehydrogenase complex (PDC). In this study we have examined the breakdown of T-cell tolerance to self-PDC using a mouse model. Female SJL/J mice were sensitized intraperitoneally with foreign-PDC (bovine) and/or self-PDC (murine) in complete Freund's adjuvant, and serum, spleen, and liver tissue was taken 8 weeks later. Animals sensitized with foreign-PDC produced IgG antibodies that were reactive with both foreign and self-PDC, but splenic T cells from these animals only responded to stimulation with foreign PDC. Sensitization with self-PDC elicited neither antibodies nor reactive T cells. Significantly, cosensitization with mixed self-PDC and foreign-PDC resulted in a full breakdown of self-tolerance, with generation of both antibody and T-cell responses to self-PDC of the type seen exclusively in human PBC patients. Mild bile duct lesions deficient in CD8(+) T cells were seen 8 weeks after sensitization with either foreign or self-PDC. However, after sensitization with mixed self-PDC and foreign-PDC, these lesions were significantly larger and heavily infiltrated by CD8(+) T cells. Liver-infiltrating T cells derived from the self-PDC and foreign-PDC cosensitized but not from control animals showed reactivity with self-PDC, suggesting a possible role for autoreactive PDC-specific T-cell responses in the pathogenesis of the observed histologic changes. It is likely that B-cell cross-reactivity between foreign and self-PDC enhances the potential for breakdown of T-cell self-tolerance by allowing efficient presentation of self-antigens in the inoculum. This model may provide a useful system for investigating the etiology and treatment of PBC.