8-(3-hydroxyphenyl)octanal | 157888-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 8-(3-hydroxyphenyl)octanal
• 英文别名: 8-(3-hydroxyphenyl)-octanal
• CAS: 157888-43-2
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: CZECIKXGUYQZJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(3-hydroxyphenyl)octanal 在 氢氧化钾 、 一水合肼 、 二乙二醇 作用下， 以 二乙二醇 为溶剂， 反应 10.0h， 生成 3-n-octylphenol
  参考文献：
  名称：

  西洋参（Anacardium occidentale）（腰果）中酚类的臭氧化作用

  摘要：

  AbstractThe phenolic lipid components cardanol and cardol, obtained from heat‐processed technical cashew nutshell liquid from Anacardium occidentale, and anacardic acid from the natural product, each containing monoene, diene, and triene constituents, were ozonized. The ozonides were reduced chemically and catalytically to give 8‐(3‐hydroxyphenyl)octanal, 8‐(3,5‐dihydroxyphenyl)octanal, and 8‐(3‐hydroxy‐2‐carboxyphenyl)octanal, respectively, together with formaldehyde, malondialdehyde, butanal, and heptanal in each case. Reduction of the 8‐(3‐hydroxyphenyl)octanal, which was synthesized from 3‐benzyloxybenzaldehyde, gave 3‐octylphenol. Oxidation of the aldehyde with potassium permanganate gave 8‐(3‐hydroxyphenyl)octanoic acid, and reduction with sodium borohydride yielded 8‐(3‐hydroxyphenyl)octanol. For comparison, the trans‐diols of cardanol were prepared by treatment of cardanol with peroxyformic acid and cleaved by periodate oxidation to give an alternative route to 8‐(3‐hydroxyphenyl)octanal but in lower yield. Likewise, the cis‐diols were obtained with potassium permanganate and cleaved without isolation to give the same product in lower yield compared with ozonization.

  DOI：

  10.1007/s11746-002-0549-8
• 作为产物：
  描述：

  M-[(Z)-8-十五碳烯基]苯酚 在 臭氧 、 溶剂黄146 、 锌 作用下， 生成 庚醛 、 8-(3-hydroxyphenyl)octanal
  参考文献：
  名称：

  Antitumor principles from Ginkgo biloba L.

  摘要：

  从银杏叶中分离出了七种长链酚，其中的三种，即银杏酸（Ib）、双叶酚（IIa）和贲门醇（IIIa），对小鼠肉瘤 180 腹水具有抗肿瘤活性。按照总包装细胞体积法，在 40 mg/kg/d 的剂量下，Ib、IIa 和 IIIa 的抗肿瘤效果分别为 (+ +)、(+ + +)和 (+ + +)。

  DOI：

  10.1248/cpb.35.3016

文献信息

• Antitumor principles from Ginkgo biloba L.
  作者：HIDER ITOKAWA、NOBUO TOTSUKA、KEISUKE NAKAHARA、KOICHI TAKEYA、JEAN-PIERRE LEPOITTEVIN、YOSHINORI ASAKAWA

  DOI：10.1248/cpb.35.3016

  日期：——

  Seven long-chain phenols were isolated from Ginkgo biloba L. Three of them, anacardic acid (Ib), bilobol (IIa), and cardanol (IIIa), showed antitumor activity against Sarcoma 180 ascites in mice. The antitumor effectiveness was rated (+ +) for Ib, (+ + +) for IIa, and (+ + +) for IIIa at 40 mg/kg/d by the total packed cell volume method.

  从银杏叶中分离出了七种长链酚，其中的三种，即银杏酸（Ib）、双叶酚（IIa）和贲门醇（IIIa），对小鼠肉瘤 180 腹水具有抗肿瘤活性。按照总包装细胞体积法，在 40 mg/kg/d 的剂量下，Ib、IIa 和 IIIa 的抗肿瘤效果分别为 (+ +)、(+ + +)和 (+ + +)。
• Method of modifying components present in cashew nut shell liquid
  申请人：——

  公开号：US20020004576A1

  公开（公告）日：2002-01-10

  Disclosed is a process for modifying cashew nut shell liquid (CNSL) which involves the steps of subjecting the CNSL to ozonolysis to form ozonolysis reaction products, followed by reduction of the ozonolysis reaction products to give a mixture of phenolic components and aldehydes. In a preferred embodiment, the process involves reacting CNSL with ozone to form a mixture containing ozonolysis reaction products, and then treating the mixture under reducing conditions to form a further mixture containing phenolic components with an eight carbon chain having a terminal —CHO group and alkyl components of varying lengths with either one or two terminal —CHO groups. The resulting CNSL aldehydes may be used to form adhesives for use in the manufacture of composites such as wood particle board.

  本发明公开了一种腰果壳液（CNSL）改性工艺，该工艺包括以下步骤：将腰果壳液进行臭氧分解以形成臭氧分解反应产物，然后还原臭氧分解反应产物以得到酚类成分和醛类的混合物。在一个优选的实施方案中，该工艺包括将 CNSL 与臭氧反应，形成一种含有臭氧分解反应产物的混合物，然后在还原条件下处理该混合物，形成另一种混合物，其中含有具有一个末端 -CHO 基团的八碳链酚类成分和具有一个或两个末端 -CHO 基团的不同长度的烷基成分。生成的 CNSL 醛类可用于形成粘合剂，用于制造木质刨花板等复合材料。
• METHOD OF MODIFYING COMPONENTS PRESENT IN CASHEW NUT SHELL LIQUID
  申请人：Cambridge Biopolymers Limited

  公开号：EP1131277B1

  公开（公告）日：2005-07-13
• US6869989B2
  申请人：——

  公开号：US6869989B2

  公开（公告）日：2005-03-22
• US7074872B2
  申请人：——

  公开号：US7074872B2

  公开（公告）日：2006-07-11