(E)-2-甲氧基-4-(1-丙烯基苯酚) | 5932-68-3

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (E)-2-甲氧基-4-(1-丙烯基苯酚)
• 英文名称: (E)-2-methoxy-4-(1-propenyl)phenol
• 英文别名: trans-isoeugenol；(E)-isoeugenol；isoeugenol；(E)-2-methoxy-4-(prop-1-en-1-yl)phenol；2-methoxy-4-[(E)-prop-1-enyl]phenol
• CAS: 5932-68-3
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD00009285
• 分子量: 164.204
• InChiKey: BJIOGJUNALELMI-ONEGZZNKSA-N

物化性质

• 熔点：
  33°
• 沸点：
  bp12 140°
• 密度：
  d420 1.087
• LogP：
  2.1 at 25℃
• 物理描述：
  Isoeugenol is a pale yellow oily liquid with a spice-clove odor. Freezes at 14°F. Density 1.08 g / cm3. Occurs in ylang-ylang oil and other essential oils.
• 颜色/状态：
  Oily liquid; easily becomes somewhat yellow
• 气味：
  Spice-clove odor
• 闪点：
  >212 °F(>100 °C)(closed cup)
• 溶解度：
  In water, 810 mg/L at 25 °C
• 蒸汽压力：
  0.02 mm Hg at 77 °F (NTP, 1992)
• 分解：
  When heated to decomposition it emits acrid smoke and fumes.
• 粘度：
  7.476 centipoise at 20 °C
• 汽化热：
  14681.396 cal/g mole at normal boiling point
• 表面张力：
  30.813 dynes/cm
• 折光率：
  Index of refraction = 1.5739 at 19 °C
• 解离常数：
  pKa = 9.88 at 25 °C
• 保留指数：
  1429;1436.4;1420;1409;1411;1418.9

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

在口服给予（14）C-异丁子香酚（156 mg/kg，50 uCi/kg）单次剂量后，72小时内超过85%的给药剂量主要以硫酸盐或葡萄糖醛酸代谢物的形式通过尿液排出。大约10%在粪便中回收，不到0.1%以CO(2)或呼出的有机物形式回收。在任何分析的时间点，血液中均未检测到母体异丁子香酚。静脉给药（15.6 mg/kg，100 uCi/kg）后，异丁子香酚迅速从血液中消失。半衰期为12分钟，Cl(s)为1.9 L/min/kg。排泄特性与口服给药相似。在72小时内，所选组织中残留的总放射性物质量不到口服或静脉给药剂量的0.25%。这些研究的结果表明，异丁子香酚被迅速代谢，并且主要以母体化合物的第二阶段结合物形式通过尿液排出。

Following a single oral dose of (14)C-isoeugenol (156 mg/kg, 50 uCi/kg), greater than 85% of the administered dose was excreted in the urine predominantly as sulfate or glucuronide metabolites by 72 hr. Approximately 10% was recovered in the feces, and less than 0.1% was recovered as CO(2) or expired organics. No parent isoeugenol was detected in the blood at any of the time points analyzed. Following iv administration (15.6 mg/kg, 100 uCi/kg), isoeugenol disappeared rapidly from the blood. The half life was 12 min and the Cl(s) was 1.9 L/min/kg. Excretion characteristics were similar to those of oral administration. The total amount of radioactivity remaining in selected tissues by 72 hr was less than 0.25% of the dose following either oral or intravenous administration. Results of these studies show that isoeugenol is rapidly metabolized and is excreted predominantly in the urine as phase II conjugates of the parent compound.

来源:Hazardous Substances Data Bank (HSDB)

代谢

已知反式异丁子香酚在人体内的代谢物包括反式异丁子香酚-O-葡萄糖苷酸。

Trans-isoeugenol has known human metabolites that include trans-Isoeugenol-O-glucuronide.

来源:NORMAN Suspect List Exchange

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 副作用

皮肤致敏剂 - 一种可以诱导皮肤产生过敏反应的制剂。

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。根据需要执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或将其置于左侧卧位（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗救助。 /酚类及其相关化合物/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Phenols and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有必要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时进行治疗……。监测休克并在必要时进行治疗……。预期可能出现癫痫并在必要时进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。给予活性炭……。不要使用催吐剂。在去污染后，用干燥的、无菌的敷料覆盖皮肤烧伤……。保持体温。/酚类及其相关化合物/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Administer activated charcoal ... . Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑对肺水肿进行药物治疗...。监测心率和必要时治疗心律失常...。开始静脉输注D5W /SRP: "保持开放"，最低流量/。如果出现低血容量迹象，使用0.9%生理盐水（NS）或乳酸林格液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。如果病人在正常血容量下出现低血压，考虑使用血管加压药。注意液体过载的迹象...。如果病人在严重低氧血症、发绀和心脏受损（对氧疗无反应）的情况下出现症状，给予1%亚甲蓝溶液。... 使用地西泮或劳拉西泮治疗癫痫...。使用丙美卡因氢氯化物协助眼部冲洗...。/酚类及相关化合物/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... Treat seizures with diazepam or lorazepam. ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在口服给予（14）C-异丁子香酚（156 mg/kg，50 uCi/kg）单次剂量后，72小时内超过85%的给药剂量主要以硫酸盐或葡萄糖醛酸代谢物的形式通过尿液排出。大约10%在粪便中回收，不到0.1%以CO(2)或呼出的有机物形式回收。在任何分析的时间点，血液中均未检测到母体异丁子香酚。静脉给药（15.6 mg/kg，100 uCi/kg）后，异丁子香酚迅速从血液中消失。半衰期为12分钟，

Following a single oral dose of (14)C-isoeugenol (156 mg/kg, 50 uCi/kg), greater than 85% of the administered dose was excreted in the urine predominantly as sulfate or glucuronide metabolites by 72 hr. Approximately 10% was recovered in the feces, and less than 0.1% was recovered as CO(2) or expired organics. No parent isoeugenol was detected in the blood at any of the time points analyzed. Following iv administration (15.6 mg/kg, 100 uCi/kg), isoeugenol disappeared rapidly from the blood. The half life was 12 min and the Cl(s) was 1.9 L/min/kg. Excretion characteristics were similar to those of oral administration. The total amount of radioactivity remaining in selected tissues by 72 hr was less than 0.25% of the dose following either oral or intravenous administration. Results of these studies show that isoeugenol is rapidly metabolized and is excreted predominantly in the urine as phase II conjugates of the parent compound.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 在 [(t-C₄H₉)4N]3PMo₄O₁₆ 双氧水 作用下， 以 叔丁醇 为溶剂， 以100%的产率得到香草醛
  参考文献：
  名称：

  Oxidation reaction process catalyzed by phase-transfer catalyst controlling reaction

  摘要：

  本发明涉及由具有一般式(R1)(R2)(R3)(R4)N)xHy[A]A或QmMO3(L)的反应控制相转移催化剂催化的氧化反应。催化剂本身在反应介质中不溶解，但可以在其中一个反应物的作用下形成可溶解于反应介质中的活性物种。活性物种反过来可以选择性地与另一个反应物发生反应。当其中一个反应物完全消耗时，催化剂将从反应体系中分离出来，并可以通过简单的分离方法进行回收。回收的催化剂可以以与原始催化剂相当的效率进行循环利用。所述催化剂的分离类似于异相催化剂的分离，而在反应过程中，所述催化剂将完全表现出均相催化剂的特性。该催化氧化反应体系特别适用于从环己烯生产环氧环己烷或从丙烯生产环氧丙烷的大规模工业生产。

  公开号：

  US20040030054A1
• 作为产物：
  描述：

  丁香酚 在 hexaaquaruthenium(II) 作用下， 以 氘代乙醇 、 重水 为溶剂， 反应 24.0h， 以99%的产率得到(E)-2-甲氧基-4-(1-丙烯基苯酚)
  参考文献：
  名称：

  六甲基钌（2+）离子催化的烯烃异构化。初步沟通

  摘要：

  六氢化钌（2+）离子催化烯烃的异构化，特别是烯丙基向乙烯基醚的有用转化，在温和条件下产生（E）异构体。

  DOI：

  10.1002/hlca.19920750514

文献信息

• Reductive Coupling between C–N and C–O Electrophiles
  作者：Rong-De He、Chun-Ling Li、Qiu-Quan Pan、Peng Guo、Xue-Yuan Liu、Xing-Zhong Shu

  DOI：10.1021/jacs.9b05224

  日期：2019.8.14

  The cross-electrophile reaction is a promising strategy for C-C bond formation. Recent studies have focused mainly on reactions with organic halides. Here we report a coupling reaction between C-N and C-O electrophiles that demonstrates the possibility of constructing a C-C bond via C-N and C-O cleavage. Several reactions between benzyl/aryl ammonium salts and vinyl/aryl C-O electrophiles have been

  交叉亲电反应是 CC 键形成的一个有前景的策略。最近的研究主要集中在与有机卤化物的反应上。在这里，我们报告了 CN 和 CO 亲电试剂之间的偶联反应，证明了通过 CN 和 CO 裂解构建 CC 键的可能性。已经研究了苄基/芳基铵盐和乙烯基/芳基 CO 亲电试剂之间的几种反应。初步机理研究表明，苄基铵是通过自由基机制活化的。
• HAIR COLORING COMPOSITIONS
  申请人：——

  公开号：US20020032933A1

  公开（公告）日：2002-03-21

  A hair coloring composition comprising: (a) from about 0.0003 moles (per 100 g of composition) to less than about 0.09 moles (per 100 g of composition) of an inorganic peroxygen oxidizing agent; and (b) an oxidative hair coloring agent; wherein the pH of each of (a) and (b) is in the range of from about 1 to about 6 and wherein the combined mixture of (a) and (b) has a pH in the range of from about 1 to about 6. The products can provide excellent hair coloring and in-use efficacy benefits including excellent initial color and good wash fastness in combination with reduced hair damage at low pH.

  一种染发组合物，包括：(a)约0.0003摩尔（每100克组合物）至约0.09摩尔（每100克组合物）的无机过氧化氧化剂；和(b)氧化性染发剂；其中(a)和(b)的pH值在约1至约6的范围内，且(a)和(b)的混合物的pH值在约1至约6的范围内。该产品可以提供出色的染发效果和使用效果，包括出色的初始颜色和良好的耐洗性，同时在低pH值下减少头发损伤。
• Hair colouring and conditioning compositions
  申请人：The Procter & Gamble Company

  公开号：US20030113286A1

  公开（公告）日：2003-06-19

  A hair colouring and conditioning composition comprising: (a) a hair colouring agent; and (b) a hair conditioning agent; wherein the composition provides an Average Combing Index Value of greater than 1.2 as measured by the Combing Technical Test Method. The products can provide excellent hair colouring together with excellent conditioning, reduced hair damage, brittleness and dryness, and is convenient and easy to use.

  一种包括： (a) 染发剂；和 (b) 护发剂； 的染发和护理组合物； 其中该组合物通过梳理技术测试方法测得的平均梳理指数值大于1.2。 该产品可以提供优秀的染发效果以及优秀的护理效果，减少头发损伤、脆弱和干燥，且使用方便。
• Kinetic Study on the Free Radical-Scavenging and Vitamin E-Regenerating Actions of Caffeic Acid and Its Related Compounds
  作者：Keishi Ohara、Yoko Ichimura、Kumi Tsukamoto、Mayumi Ogata、Shin-ichi Nagaoka、Kazuo Mukai

  DOI：10.1246/bcsj.79.1501

  日期：2006.10

  A kinetic study involving 4-hydroxycinnamic acid derivatives (HCAs) was performed in order to clarify the mechanism for free radical-scavenging and vitamin E-regenerating. The second-order rate con...

  为了阐明自由基清除和维生素 E 再生的机制，进行了涉及 4-羟基肉桂酸衍生物 (HCA) 的动力学研究。二阶速率控制...
• PREVENTION OF BODY ODOUR
  申请人：Huchel Ursula

  公开号：US20120164097A1

  公开（公告）日：2012-06-28

  Bad odors on textile materials are often caused by body odor. The invention relates to a textile material treatment method for inhibiting body odor on textile materials, by which means the treated textiles, after having been worn, even after sweat-inducing sports activities, have a significantly reduced bad odor or even no odor. The invention also relates to a perfume composition and to a textile material treatment agent, respectively comprising urea derivatives and/or phenacylthiazolium salts, that counteract the formation of body odor.

  纺织材料上的不良气味通常是由体臭引起的。本发明涉及一种抑制纺织材料上体臭的纺织材料处理方法，通过该方法处理的纺织品，即使在进行导致出汗的运动活动后穿着，也能显著减少不良气味甚至没有气味。本发明还涉及一种香水组合物以及一种纺织材料处理剂，分别包含尿素衍生物和/或苯乙基亚砜盐，它们能对抗体臭的形成。

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