对叔丁基苯基1-(2,3-环氧)丙基醚 | 2186-24-5

• 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 - 苯酚醚
• 中文名称: 对叔丁基苯基1-(2,3-环氧)丙基醚
• 中文别名: [(甲基苯氧基)甲基]环氧乙烷；2-(4-甲基苯氧基)甲基环氧乙烷；2-对甲苯氧基甲基环氧乙烷；甲苯基缩水甘油醚
• 英文名称: cresyl-glicidyl ether
• 英文别名: 2-((p-tolyloxy)methyl)oxirane；2-(4-methylphenoxy)methyl oxirane；4-methylphenyl glycidyl ether；1-(4-methylphenoxy)-2,3-epoxypropane；Cresyl glycidyl ether；2-[(4-methylphenoxy)methyl]oxirane
• CAS: 2186-24-5；26447-14-3
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD00046991
• 分子量: 164.204
• InChiKey: CUFXMPWHOWYNSO-UHFFFAOYSA-N

物化性质

• 沸点：
  231.67°C (rough estimate)
• 密度：
  1.0041 (rough estimate)
• 物理描述：
  Cresyl glycidyl ether is a colorless liquid. Sinks and mixes with water. (USCG, 1999)
• 颜色/状态：
  Clear, colorless Liquid
• 闪点：
  less than 200 °F (NTP, 1992)
• 溶解度：
  In water, 930 mg/L at 25 °C (est)
• 蒸汽压力：
  4.3X10-2 mm Hg at 25 °C (est)
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 粘度：
  5 to 25 cm/sec at 25 °C
• 燃烧热：
  -16,500 Btu/lb = -9,190 cal/g = -384x10 5 J/kg

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

o-克利基甘油醚在体外与豚鼠肝脏匀浆孵化时，迅速转化为相应的二醇化合物。

o-Cresyl glycidyl ether was converted rapidly to the corresponding diol compounds when incubated with guinea pig liver homogenate in vitro. /o-Cresyl glycidyl ether/

来源:Hazardous Substances Data Bank (HSDB)

代谢

对来自人、大鼠和小鼠的肝脏和肺部的微粒体和细胞溶质组分的研究表明，邻甲苯基缩水甘油醚是谷胱甘肽转移酶的良好底物，其中小鼠在酶促谷胱甘肽结合反应中效率最高。总体而言，环氧化合物的酶促水解是邻甲苯基缩水甘油醚在体外生物转化的最重要途径，其中最高活性位于微粒体中。人类样本通常比小鼠或大鼠的水解效率更高。/邻甲苯基缩水甘油醚/

Studies in preparations of microsomal and cytosolic fractions of liver and lung derived from human, rat, and mouse showed that o-cresyl glycidyl ether is a good substrate for glutathione tranferase, with mice being the most efficient in enzymatic glutathione conjugation. Overall, enzymatic hydrolysis of the epoxide group is the most important route of in vitro biotransformation of o-cresyl glycidyl ether, with the highest activity located in the microsomes. Human samples generally had a higher efficiency for hydrolysis than mice or rats. /o-Cresyl glycidyl ether/

来源:Hazardous Substances Data Bank (HSDB)

代谢

大鼠在单次腹腔注射高达164 mg/kg剂量的o-环己基缩水甘油醚后，尿液中代谢物谱显示，谷胱甘肽（GSH）结合和环氧化物的水解是o-环己基缩水甘油醚的关键生物转化途径。在低剂量水平，GSH结合和水解各占尿液代谢物的大约25％；然而，在高剂量时，环氧化物的水解成为最显著的解毒途径（40％）。

The urinary metabolite profile of o-cresyl glycidyl ether in rats, following ip administration of single doses up to 164 mg/kg, indicated that glutathione (GSH) conjugation and epoxide hydrolysis were key biotransformation pathways of o-cresyl glycidyl ether. At low dose levels GSH conjugation and epoxide hydrolysis accounted each for about 25% of urinary metabolites; however at higher doses epoxide hydrolysis became the most prominent route of detoxification (40%). /o-Cresyl glycidyl ether/

来源:Hazardous Substances Data Bank (HSDB)

代谢

酚基缩水甘油醚（PGE）及其结构类似物邻甲酚缩水甘油醚（oCGE）的尿代谢物轮廓在雄性Wistar大鼠中得到了确定。使用定量分析方法研究了PGE和oCGE的代谢物、它们的剂量排泄关系以及尿排泄动力学。大鼠通过腹腔注射PGE或oCGE，剂量范围从0.033到1.0 mmol/kg。...用oCGE处理的 rats 排泄出 oCGEMA、COLA 和 NAPS，表明 PGE 和 oCGE 的代谢物轮廓相似。开发的用于确定PGE和oCGE的尿巯基酸代谢物的定量方法具有足够的选择性和灵敏度，可以测定低至0.033mmol/kg的剂量。作者认为该方法可以用于低潜在暴露的人类。应进一步调查这些缩水甘油醚的乳酸和新型丝氨酸代谢物的人类排泄，因为这些环氧化物的可能灭活是通过环氧化物的水解介导途径。

The urinary metabolite profiles of phenyl-glycidyl-ether (PGE) and its structural analogue ortho-cresyl-glycidyl-ether (oCGE) were determined in male Wistar-rats. Quantitative analytical methods were used to investigate the metabolites of PGE and oCGE, their dose excretion relationships and urinary excretion kinetics. Rats were dosed intraperitoneally with PGE or oCGE in doses ranging from 0.033 to 1.0 mmol/kg. ...Rats treated with oCGE excreted oCGEMA, COLA, and NAPS, showing that the metabolite profiles of PGE and oCGE were comparable. The quantitative methods developed to determine the urinary mercapturic-acid metabolites of PGE and oCGE offered enough selectivity and sensitivity for their determination as low as 0.033mmol/kg. The authors conclude the method can be used for humans with low potential exposures. Human excretion of lactic-acid and the novel serine metabolites of these glycidyl ethers should be further investigated, as possible inactivation of these epoxides may be by epoxide hydrolysis mediated routes.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在皮肤渗透过程中，所有的GE都被广泛代谢成相应的（双）二醇。几乎没有任何YX4000，只有非常少量的C12GE和BADGE未改变地穿透皮肤，但大量的HDDGE和o-CGE未改变地穿透了皮肤。对于o-CGE，但没有其他GE，未改变穿透皮肤的剂量百分比随时间增加。五种选定的GE在反应中观察到的大变异表明，GE不应被视为单一类化合物，而应基于它们的个别特性来考虑。

... During skin penetration, all GE were extensively metabolized to their corresponding (bis-)diols. Virtually no YX4000, and only very small amounts of C12GE and BADGE, penetrated the skin unchanged, but significant amounts of HDDGE and o-CGE penetrated the skin unchanged. For o-CGE, but none of the other GE, the percentage of the applied dose that penetrated the skin unchanged increased over time. The large variation in response observed with the five selected GE indicates that GE should not be considered as a single class of compounds but rather on the basis of their individual properties.

来源:Hazardous Substances Data Bank (HSDB)

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

• 毒性数据

LC50 (大鼠) = 1,220 ppm/4小时

LC50 (rat) = 1,220 ppm/4h

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

毒理性

• 解毒与急救

皮肤接触后应立即彻底用肥皂和水清洗，并重复多次。不要使用溶剂来去除。眼睛接触需要立即用清水冲洗，并咨询医生。

Skin contact should be followed by thorough and repeated washing with soap and water. Do not use solvents to remove it. Eye contact requires flushing with water immediately and consultation with a physician.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，并在需要时辅助通气。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……。预测并处理癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……。不要使用催吐剂。对于误食，如果患者能吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克、最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于无意识、严重肺水肿或呼吸停止的患者，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。监测心率和必要时治疗心律失常。 ... 开始静脉输液，使用D5W/SRP：“保持开放”，最低流量/。如果出现低血容量的迹象，使用乳酸钠林格氏液。注意液体过载的迹象。考虑使用药物治疗肺水肿。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象。用 Diazepam（安定）治疗癫痫。使用丙美卡因氢氯化物协助眼部冲洗。 /毒药A和B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

体外皮肤渗透研究表明，使用人鼠皮肤和整体小鼠皮肤，o-环己基缩水甘油醚具有渗透皮肤的能力。渗透性顺序为：小鼠>大鼠>人类。o-环己基缩水甘油醚渗透入皮肤后迅速被水解；然而，可能有至少10%的施用剂量以未改变的物质形式存在于通过皮肤吸收之后。

In vitro skin penetration studies with dermatomized human and rat skin and whole mouse skin indicated that o-cresyl glycidyl ether has a potential to penetrate the skin. Permeability was in the order: mouse>rat>human. o-Cresyl glycidyl ether is rapidly hydrolyzed after penetration into the skin; however, a minimum of 10% of the applied dose may be present as unchanged material after absorption through the skin. /o-Cresyl glycidyl ether/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

环氧基乙醚（GE）是一类重要的工业化学品，被认为在体内具有潜在的诱变作用，因为一些GE在短期的体外测试中被证明是直接的诱变剂。本研究在新鲜的、全层C3H小鼠、人类皮肤和Fisher 344大鼠皮肤上，研究了不同类别GE代表物质的经皮渗透和代谢，以确定表观渗透常数、滞后时间和代谢轮廓。通过将相应的醇与环氧氯丙烷反应，合成了五种不同的GE，包括双酚A的二缩水甘油醚（BADGE）、4,4'-二羟基-3,3',5,5'-四甲基联苯（Epikote YX4000）和1,6-己二醇（HDDGE）以及1-十二醇（C12GE）和邻甲酚（o-CGE）的GE。它们的放射性同位素类似物是使用[U-14C]-环氧氯丙烷合成的。五种GE之间的经皮渗透性有很大的差异（四个数量级）。一般来说，通过全层小鼠皮肤的渗透性高于通过皮肤磨削的大鼠皮肤，而人类皮肤磨削的渗透性最低。渗透性按YX4000 < BADGE < C12GE < o-CGE < HDDGE的顺序增加。五种GE的相对皮肤渗透性在很大程度上可以通过化合物的亲脂性（以log P(o/w)表示）与分子量的结合来解释。

Glycidyl ethers (GE), an important class of industrial chemicals, are considered to be potentially mutagenic in vivo because some GE have been shown to be direct mutagens in short-term in vitro tests. The percutaneous penetration and metabolism of representatives of different classes of GE was studied in the fresh, full-thickness C3H mouse, and dermatomed human and Fisher 344 rat skin to determine the apparent permeability constants, lag times and metabolic profiles. Five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabelled analogues were synthesized with a 14C-label using [U-14C]-epichlorohydrin. There was a large variation (four orders of magnitude) in percutaneous penetration between the five GE. In general, penetration through full-thickness mouse skin was higher than through dermatomed rat skin, whereas dermatomed human skin was the least permeable. The permeability increased in the order YX4000 < BADGE < C12GE < o-CGE < HDDGE. The relative skin permeability of the five GE could be explained for a significant part by the lipophilicity, expressed as log P(o/w), in combination with the molecular weight of the compounds.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2910900090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P201,P202,P261,P264,P271,P272,P273,P280,P302+P352,P304+P340,P308+P313,P312,P332+P313,P362,P391,P403+P233,P405,P501
• 危险品运输编号：
  2810
• 危险性描述：
  H315,H332,H335,H341,H411,H317,H350

反应信息

• 作为反应物：
  描述：

  对叔丁基苯基1-(2,3-环氧)丙基醚 在 sodium azide 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 以94%的产率得到1-azido-3-(4-methylphenoxy)propan-2-ol
  参考文献：
  名称：

  脂肪酶催化动力学拆分 1-Aryloxy-3-Nitrato-和 1-Aryloxy-3-Azido-2-Propanols 的外消旋混合物

  摘要：

  摘要 1-芳氧基-3-硝基-2-丙醇和1-芳氧基-3-叠氮基-2-丙醇的外消旋混合物通过脂肪酶介导的乙酸乙烯酯酰化以中等选择性拆分。研究了苯环取代基的性质、位置和空间要求对分辨率的影响。

  DOI：

  10.1080/00397919808004470
• 作为产物：
  描述：

  2-[(2-溴-4-甲基苯氧基)甲基]环氧乙烷 在 高氯酸四乙基铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 以80%的产率得到对叔丁基苯基1-(2,3-环氧)丙基醚
  参考文献：
  名称：

  Selective Reduction of the CarbonBromine Bond in Bromo Epoxides

  摘要：

  The controlled-potential electrolysis of various substituted bromo epoxides in acetonitrile at a mercury pool electrode led to selective reduction of the carbon-bromine bond affording the respective epoxide products in 80-90% yield.

  DOI：

  10.1016/s0040-4039(00)91658-7

文献信息

• METHOXYACRYLATE-BASED FUNGICIDE AND METHODS FOR PREPARING AND USING THE SAME
  申请人：YANG Guangfu

  公开号：US20100292285A1

  公开（公告）日：2010-11-18

  A pharmaceutical composition of fungicide including at least a compound represented by Formula (I). The pharmaceutical composition of fungicide can further include an emulsifier, a cosolvent, a stabilizer, and a solvent. The fungicide can prevent and treat powdery mildew, downy mildew, gray mold, brown spot, scab of vegetables and fruits, southern leaf blight of corn, rice false smut, citrus stem-end rot, and rape sclerotinia rot, with high efficiency, low toxicity, and relative environmental friendliness. A method of preparing the fungicide and a method of using thereof are also provided.

  一种包括至少一种由化学式（I）表示的化合物的杀菌剂制剂。该杀菌剂制剂还可以包括乳化剂、共溶剂、稳定剂和溶剂。该杀菌剂可以高效、低毒、相对环保地预防和治疗蔬菜和水果的白粉病、霜霉病、灰霉病、褐斑病、疮痂病、玉米南部叶枯病、水稻假穗病、柑橘果蒂腐烂病和油菜菌核病。还提供了一种制备该杀菌剂的方法和使用该杀菌剂的方法。
• An Unusual (R)-Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers
  作者：Jing Zhao、Yan-Yan Chu、Ai-Tao Li、Xin Ju、Xu-Dong Kong、Jiang Pan、Yun Tang、Jian-He Xu

  DOI：10.1002/adsc.201100031

  日期：2011.6

  ortho‐substituted phenyl glycidyl ethers and para‐nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)‐enantiopreference was unexpectedly observed for the ortho‐nitrophenyl glycidyl ether. As a proof‐of‐concept, five enantiopure epoxides (>99% ee) were obtained in high yields, and a gram‐scale preparation of

  从巨大芽孢杆菌ECU1001中克隆了一种新的环氧水解酶（BMEH），该酶具有异常的（R）-对映体选择性和很高的活性。在对位取代的苯基缩水甘油醚和对硝基苯乙烯氧化物的生物拆分中，实现了最高的对映选择性（E > 200）。值得一提的是，底物结构显着影响了酶的对映选择性，因为人们意外地观察到邻硝基硝基苯缩水甘油醚的反向（S）-对映体选择性。作为概念验证，以高收率获得了五种对映纯环氧化合物（> 99％ee），并以克级制备了（S） -邻甲基苯基缩水甘油基醚，然后成功地在几个小时内完成，这表明BMEH为光学活性的环氧化物的高效制备有吸引力的生物催化剂。
• Convenient One‐Pot Synthesis of Vinyl Ethers from Phenyl 2‐Hydroxyalkyl Selenides
  作者：Shou‐Ri Sheng、Hai‐Rong Luo、Wu‐Kang Sun、Xiao‐Ling Liu、Qin Xin、Qiu‐Ying Wang

  DOI：10.1080/00397910500296901

  日期：2005.11

  Abstract Vinyl ethers were prepared with good yields in a one‐pot, two‐step transformation by O‐alkylation reaction of phenyl 2‐hydroxyalkyl selenides with primary or secondary organic halides followed by oxidation elimination with 30% hydrogen peroxide.

  摘要 通过苯基 2-羟烷基硒化物与伯或仲有机卤化物的 O-烷基化反应，然后用 30% 的过氧化氢氧化消除，在一锅两步转化中以良好的收率制备了乙烯基醚。
• Stepwise benzylic oxygenation <i>via</i> uranyl-photocatalysis
  作者：Deqing Hu、Xuefeng Jiang

  DOI：10.1039/d1gc04042a

  日期：——

  Stepwise oxygenation of benzylic molecules with uranyl photocatalysis was realized under ambient conditions. The accuracy of the stepwise oxygenation was ensured by the tunability of redox potential in uranyl photocatalysis through solvents and additives.

  使用铀酰光催化剂，在常温下实现对苄基分子的逐步氧化。通过溶剂和添加剂调节铀酰光催化剂的氧化还原电位，确保了逐步氧化的准确性。
• Synthesis of β-hydroxy selenides using benzeneselenol and oxiranes under supramolecular catalysis in the presence of β-cyclodextrin in water
  作者：R. Sridhar、B. Srinivas、K. Surendra、N. Srilakshmi Krishnaveni、K. Rama Rao

  DOI：10.1016/j.tetlet.2005.10.094

  日期：2005.12

  efficient method for the synthesis of β-hydroxy selenides is reported at room temperature in impressive yields for the first time by the highly the regioselective ring-opening of oxiranes with benzeneselenol in water under supramolecular catalysis in the presence of β-cyclodextrin. This is a direct one-pot synthesis of β-hydroxy selenides under mild conditions using water as solvent and has many advantages

  在室温下，在超分子催化下，在β-环糊精的存在下，超氧催化下苯乙烯醇与氧杂苯环的区域选择性高开环，这是首次在室温下以高产率收率合成β-羟基硒化物的简单有效方法。这是在温和条件下使用水作为溶剂直接进行一锅法合成的β-羟基硒化物，与现有方法相比，具有许多优势。β-环糊精也可以回收再利用。

表征谱图