甲基丙烯酸异癸酯 | 142600-07-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 甲基丙烯酸异癸酯
• 中文别名: 2-甲基-2-丙烯酸异癸酯；异癸基甲基丙烯酸酯；I-甲基丙烯酸癸酯
• 英文名称: iso-decyl methacrylate
• 英文别名: isodecyl methacrylate；isodecylmethacrylate；8-methylnonyl 2-methylprop-2-enoate
• CAS: 142600-07-5；29964-84-9
• 化学式: C₁₄H₂₆O₂
• mdl: MFCD00053728
• 分子量: 226.359
• InChiKey: COCLLEMEIJQBAG-UHFFFAOYSA-N

物化性质

• 熔点：
  -22°C
• 沸点：
  126 °C10 mm Hg(lit.)
• 密度：
  0.878 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 物理描述：
  Isodecyl methacrylate is a clear liquid. (NTP, 1992)
• 溶解度：
  less than 1 mg/mL at 70° F (NTP, 1992)
• 蒸汽压力：
  0.012 mm Hg @ 25 °C /Estimated/
• 稳定性/保质期：

  Shelf life: 6 months at max. 30 °C from date of delivery (standard stabilized product).

• 分解：
  When heated to decomp it emits acrid smoke and fumes.
• 聚合：
  Methyl methacrylate, and in general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates. None the less, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper. /Methacrylates/
• 折光率：
  Index of refraction 1.4410 @ 25 °C/D

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.785
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

小量的甲基丙烯酸甲酯可以通过皂化作用轻易地代谢成醇和甲基丙烯酸。后者可以形成一个乙酰辅酶衍生物，然后进入正常的脂质代谢。/甲基丙烯酸甲酯/

Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme derivative, which then enters the normal lipid metabolism. /Methacrylates/

来源:Hazardous Substances Data Bank (HSDB)

代谢

丙烯酸酯和甲基丙烯酸酯主要通过迈克尔加成反应或谷胱甘肽-S-转移酶与谷胱甘肽结合来进行解毒。它们还可能通过羧酸酯酶发生水解。较低分子量的酯类被迅速代谢和排出，因此，不太可能引起累积毒性。/甲基丙烯酸酯/

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity. /Methacrylates/

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

• 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，如有需要，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，如有必要进行治疗……。监测休克，如有必要进行治疗……。预见并处理癫痫发作……。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。对于摄入，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。用地西泮（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)

毒理性

• 非人类毒性摘录

实验室动物：急性暴露/甲基丙烯酸iv给药增加了麻醉犬的呼吸频率，降低了心率，并产生了心电图变化。甲基丙烯酸、甲基、正丙基、正丁基、异丁基和羟乙基甲基丙烯酸酯产生双相反应，血压急剧下降后继之以二次上升。2-乙基己基、isodecyl、月桂基和叔丁基氨基乙基甲基丙烯酸酯仅产生低血压效应。二甲基氨基乙基甲基丙烯酸酯仅产生高血压效应。

/LABORATORY ANIMALS: Acute Exposure/ Methacrylic acid administration iv increased respiratory rate, decreased heart rate, & produced electrocardiogram changes in anesthetized dogs. Methacrylic acid, methyl, n-propyl, n-butyl, isobutyl, and hydroxyethyl methacrylates produced a biphasic response, an abrupt fall in blood pressure followed by a secondary rise. 2-ethylhexyl, isodecyl, lauryl, and tert-butylaminoethyl methacrylates produced only a hypotensive effect. Dimethylaminoethylmethacrylate produced only a hypertensive effect.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：发育或生殖毒性...六种甲基丙烯酸酯在怀孕大鼠的第5、10和15天给予，剂量高达急性腹膜LD50的三分之一。使用的最大剂量分别为甲基0.44、乙基0.40、正丁基0.78、异丁基0.46和isodecyl甲基丙烯酸酯0.82 ml / kg。在最高剂量下，血管瘤增加，吸收也增加。胎儿体重降低。丙烯酸剂量高达0.0075 ml / kg，与吸收和血管瘤有关。报告了胎儿死亡率和最高16%的畸形发生率...。

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... Six types of methacrylate esters /were admin/ to pregnant rats on days 5, 10 and 15 of gestation in doses up to one-third the acute intraperitoneal LD50. The maximum doses used were 0.44, 0.40, 0.78, 0.46 and 0.82 ml/kg for the methyl, ethyl, n-butyl, isobutyl, isodecyl methacrylate respectively. Hemangiomas were increased at the highest doses as were resorptions. The fetal wt was reduced by treatment. Acrylic acid was injected in volume of up to 0.0075 ml/kg and this was associated with resorptions and hemangiomas. Fetal mortality and an incidence of up to 16% malformations were reported ... .

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  TSCA listed

反应信息

• 作为反应物：
  描述：

  1,3,5-三溴-2-亚硝基-苯 、 甲基丙烯酸异癸酯 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Smith, Peter; Maples, Kirk Randall; Lau, Ramona Lillian, Canadian Journal of Chemistry, 1992, vol. 70, p. 116 - 120

  摘要：

  DOI：
• 作为产物：
  描述：

  异十醇 、 二甲基二氯化锡 、 4-甲氧基苯酚 、 甲基丙烯酸甲酯 在 sodium methylate 、 对苯二酚 作用下， 以 正庚烷 为溶剂， 以97.6%的产率得到甲基丙烯酸异癸酯
  参考文献：
  名称：

  Organotin catalyzed transesterification

  摘要：

  单羧酸酯与1,2-和1,3-多元醇通过在催化剂有效量的二烷氧化锡与过量的二烷基氯化锡混合物的存在下反应，进行酯交换反应，从而形成单羧酸酯的多元醇酯。本文还揭示了利用二甲基锡催化剂对甲基或乙基单酸酯或多酸酯与醇或多元醇进行酯交换反应，从而形成的醇或多元醇羧酸酯基本上不含有有机锡催化剂。本文还揭示了通过上述方法生产的羧酸酯，以及不含有有机锡催化剂的羧酸酯。

  公开号：

  US05498751A1

文献信息

• [EN] BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS<br/>[FR] COMPOSÉS BENZAMIDE OU BENZAMINE À UTILISER EN TANT QU'ANTICANCÉREUX POUR LE TRAITEMENT DE CANCERS HUMAINS
  申请人：UNIV TEXAS

  公开号：WO2017007634A1

  公开（公告）日：2017-01-12

  The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not affect normally dividing cells.

  所描述的发明提供了用于治疗对胆固醇生物合成抑制作出反应的肿瘤的小分子抗癌化合物。这些化合物选择性地抑制肿瘤来源的癌细胞中的胆固醇生物合成途径，但不影响正常分裂的细胞。
• AMPHOTERICIN B DERIVATIVES WITH IMPROVED THERAPEUTIC INDEX
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20160215012A1

  公开（公告）日：2016-07-28

  Provided are certain derivatives of amphotericin B (AmB) characterized by reduced toxicity and retained anti-fungal activity. Certain of the derivatives are C16 urea derivatives of AmB. Certain of the derivatives are C3, C5, C8, C9, C11, C13, or C15 deoxy derivatives of AmB. Certain of the derivatives include C3′ or C4′ modifications of the mycosamine appendage of AmB. Also provided are methods of making AmB derivatives of the invention, pharmaceutical compositions comprising AmB derivatives of the invention, and methods of use of AmB derivatives of the invention.

  提供了一些特定的两性霉素B（AmB）衍生物，其具有降低毒性和保留抗真菌活性的特点。其中一些衍生物是AmB的C16脲衍生物。其中一些衍生物是AmB的C3、C5、C8、C9、C11、C13或C15去氧衍生物。其中一些衍生物包括对AmB的甲氨葡萄糖胺附属物的C3′或C4′修饰。还提供了制备该发明的AmB衍生物的方法，包括该发明的AmB衍生物的药物组合物，以及该发明的AmB衍生物的使用方法。
• [EN] UREA DERIVATIVES OF AMPHOTERICIN B DERIVED FROM SECONDARY AMINES<br/>[FR] DÉRIVÉS D'URÉE DE L'AMPHOTÉRICINE B DÉRIVÉE D'AMINES SECONDAIRES
  申请人：UNIV ILLINOIS

  公开号：WO2016112243A1

  公开（公告）日：2016-07-14

  Provided are certain urea derivatives of amphotericin B (AmB) having improved therapeutic index compared to AmB. The compounds of the invention are less toxic than AmB and are useful to treat fungal infections. In certain embodiments the urea derivative of AmB is a compound represented by formula (I) or a pharmaceutically acceptable salt thereof: wherein, independently for each occurrence: R represents methyl, ethyl, propyl, or isopropyl; R' represents methyl, ethyl, propyl, or isopropyl; or R and R', taken together with the nitrogen atom to which they are attached, represent a radical of a cyclic secondary amine. Also provided are methods for making the urea derivatives of AmB.

  提供了与两性霉素B（AmB）相比具有改善的治疗指数的某些尿素衍生物。本发明的化合物比AmB毒性更小，并且可用于治疗真菌感染。在某些实施例中，AmB的尿素衍生物是由以下式（I）表示的化合物或其药用可接受的盐：其中，对于每次出现独立地：R代表甲基、乙基、丙基或异丙基；R'代表甲基、乙基、丙基或异丙基；或R和R'与它们连接的氮原子一起表示环状二级胺的基团。还提供了制备AmB的尿素衍生物的方法。
• Derivatives of Amphotericin B
  申请人：Revolution Medicines, Inc.

  公开号：US20160304548A1

  公开（公告）日：2016-10-20

  Disclosed are derivatives of amphotericin B (AmB) characterized by improved therapeutic index compared to AmB. The AmB derivatives include C16 ureas, carbamates, and amides according to Formula (I); C3′-substituted C16 ureas, carbamates, and amides according to Formula (II); C16 acyls according to Formula (III); C2′epi-C16 ureas, carbamates, and amides according to Formula (IV); and C16 oxazolidinone derivatives according to Formula (V). Also disclosed are pharmaceutical compositions comprising the AmB derivatives, and therapeutic methods of using the AmB derivatives.

  披露了与AmB相比具有改善的治疗指数的Amphotericin B（AmB）衍生物。这些AmB衍生物包括根据公式（I）的C16脲、碳酸酯和酰胺；根据公式（II）的C3′-取代的C16脲、碳酸酯和酰胺；根据公式（III）的C16酰基；根据公式（IV）的C2′epi-C16脲、碳酸酯和酰胺；以及根据公式（V）的C16噁唑烷酮衍生物。还披露了包括这些AmB衍生物的药物组合物，以及使用这些AmB衍生物的治疗方法。
• [EN] OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] LIGANDS DE LIAISON À UNE OPSINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2013058809A1

  公开（公告）日：2013-04-25

  Compounds are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.

  披露了一些化合物，可用于治疗由于或与在眼睛中积累的有毒视觉循环产物有关的眼科疾病，例如干性成人黄斑变性，以及由于或与突变视蛋白的错误折叠和/或视蛋白的错误定位有关的疾病。还描述了这些化合物单独或与其他治疗剂联合使用的组合物，以及使用这些化合物和/或组合物的治疗方法。还披露了合成这些药剂的方法。