iso-Bornyl acetate | 71424-71-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: iso-Bornyl acetate
• 英文别名: bornyl acetate；[(1S,2S,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] acetate
• CAS: 71424-71-0
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: KGEKLUUHTZCSIP-JBLDHEPKSA-N

物化性质

• 物理描述：
  Liquid
• 颜色/状态：
  Colorless to very pale straw-colored liquid
• 气味：
  Pine needles
• 味道：
  Fresh, burning taste
• 沸点：
  220-224 °C
• 闪点：
  190 °F (88 °C) /closed cup/
• 溶解度：
  In water 9.721 mg/L at 25 °C (est)
• 密度：
  0.978 at °C
• 蒸汽压力：
  0.107 mm Hg at 25 °C (est)
• 稳定性/保质期：
  Stable under recommended storage conditions.
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 折光率：
  Index of refraction: 1.462-1.465 at 20 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

异冰片基醋酸在生物化学途径的第一步中会迅速水解（在几小时内）成为异冰片基醇。这种醇会与葡萄糖醛酸结合并随尿液排出（预计在几小时到几天内）。

Isobornyl acetate readily hydrolyzes (within hours) to isobornyl alcohol during the first step of its biochemical pathway. The alcohol will become conjugated with glucoronic acid and be excreted in the urine (expected within hours to days).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

鉴定和使用：异冰片酯用于肥皂、洗涤剂、乳膏和香水中。人体研究：对25名志愿者进行了最大测试。该物质在10%的浓度下测试，未产生致敏反应。动物研究：将异冰片酯原液涂抹在完整或磨损的兔皮肤上，在闭合条件下保持24小时，有轻微刺激性。将异冰片酯以0、15、90或270 mg/kg bw的剂量每天给予大鼠，持续13周。雄性大鼠在90 mg/kg和270 mg/kg/天的剂量下出现肾脏毒性的迹象，在270 mg/kg的剂量下出现肝脏毒性的迹象。在一项大鼠一代繁殖研究中调查了异冰片酯，它没有产生发育毒性。在整个给药期间，父母代雄性和雌性大鼠在100和/或300 mg/kg/d的剂量下出现过度流涎的几率增加，在妊娠期间，雌性大鼠在300 mg/kg/d的剂量下观察到低几率的尿液染色的腹部毛。

IDENTIFICATION AND USE: Isobornyl acetate is used in soaps, detergents, creams and lotions and perfumes. HUMAN STUDIES: A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 10% and produced no sensitization reactions. ANIMAL STUDIES: Isobornyl acetate applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was mildly irritating. Isobornyl acetate was administered daily to rats in doses of 0, 15, 90 or 270 mg/kg bw for 13 wk. Male rats had signs of nephrotoxicity at 90 mg/kg and 270 mg/kg/day, as well as signs of hepatotoxicity at 270 mg/kg. Isobornyl acetate was investigated in a 1-generation reproduction study in rats and it did not produce developmental toxicity. Increased incidences of excess salivation occurred in parent generation male and female rats at 100 and/or 300 mg/kg/d throughout the dosage period, and low incidences of urine-stained abdominal fur were seen in females at 300 mg/kg/d during the gestation period.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，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。如有必要，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，让患者前倾或置于左侧（如果可能，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。寻求医疗关注。 /酯类及相关化合物/

/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. /Esters 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（如有需要，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，如有必要，进行治疗……。监测休克，如有必要，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）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能够吞咽、有强烈的呕吐反射且不流口水，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。给予活性炭……。/酯类及相关化合物/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilation 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 ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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. Administer activated charcoal ... . /Esters and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、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。使用气囊阀面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。监测心率和必要时治疗心律失常……。开始静脉输注D5W TKO /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格氏液（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。注意观察液体过载的迹象……。使用丙美卡因氢氯化物协助眼部冲洗……。 /酯类和相关化合物/

/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 TKO /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 ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/HUMAN EXPOSURE STUDIES/ 对25名志愿者进行了一项最大程度测试（Kligman改良法）。在10%浓度和凡士林的作用下，该材料未产生致敏反应。

/HUMAN EXPOSURE STUDIES/ A maximization test (Kligman, modified) was carried out on 25 volunteers. The material was tested at a concentration of 10% and petrolatum and produced no sesitization reactions.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

松节油、异冰片醇醋酸酯、柠檬烯、薄荷醇和α-蒎烯作为泡沫浴（Pinimenthol）成分的经皮吸收在动物身上进行了测量，使用放射性标记的成分。药代动力学测量显示，所有测试成分在经皮吸收开始后10分钟达到最大血药水平。没有成分被优先吸收。经皮吸收10分钟后所有成分的血药水平与涉及的皮肤面积大小直接相关。

The percutaneous absorptions of camphene, isoborneol-acetate, limonene, menthol and alpha-pinene as constituents of a foam bath (Pinimenthol) were measured on animals using radioactively labelled ingredients. Pharmacokinetic measurements showed maximum blood levels for all tested ingredients 10 min after the onset of percutaneous absorption. None of the ingredients was preferentially absorbed. Blood levels of all ingredients after 10 min of percutaneous absorption were a direct function of the size of the skin area involved.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  iso-Bornyl acetate 在 ferredoxin reductase 、 [2Fe-2S] ferredoxin 、 Novosphingobium aromaticivorans DSM₁₂₄₄₄ monooxygenase CYP₁₀₁B₁ 、 还原型辅酶Ⅰ 、 bovine liver catalase 作用下， 以 aq. buffer 为溶剂， 生成 5-exo-isobornyl acetate
  参考文献：
  名称：

  使用酯导向基团提高单加氧酶活性以及类萜羟基化的区域和立体选择性

  摘要：

  来自芳族新孢子虫DSM12444的单加氧酶CYP101B1比单萜类更牢固地结合去甲肾上腺素，并以高区域选择性氧化这些底物。与紫罗兰酮相比，紫罗兰醇与CYP101B1的结合较不紧密，但产物形成的水平仍然很高，并且氧化的选择性与对母体类类异戊二烯的观察到的相似。通过CYP101B1将结构上相关的倍半萜烯内酯（+）-香紫苏内酯（9）立体选择性地羟基化为（S）-（+）-3-羟基香紫苏内酯（9a）。尽管有希望的结合数据，单萜类衍生物的营业额显示出低水平的产物形成和选择性。CYP101B1催化（1 R）-（-）-nopol（14）和顺式-茉莉酮（15），分别产生> 90％（1 R）-（-）-5-hydroxynopol（14a）和4-羟基-顺式-茉莉酮（15a） 。为开发使用CYP101B1高效，选择性地氧化单萜类底物的策略，我们研究了萜类乙酸酯的结合和催化性能。这些底物的酯官能团模拟了类异戊二烯类化

  DOI：

  10.1021/acscatal.6b01882
• 作为产物：
  描述：

  莰烯 、 溶剂黄146 在 L-酒石酸 、 硼酸 作用下， 生成 iso-Bornyl acetate
  参考文献：
  名称：

  α-羟基羧酸复合催化剂由莰烯合成乙酸异冰片酯/异龙脑的研究。

  摘要：

  本研究考察了使用 α-羟基羧酸 (HCA) 复合催化剂从莰烯制备乙酸异冰片酯/异冰片的过程。通过影响因素研究发现HCA与硼酸表现出显着的协同催化作用。在最佳条件下，以酒石酸-硼酸为催化剂时，莰烯的转化率和乙酸异冰片酯的气相色谱(GC)含量和选择性分别为92.9%、88.5%和95.3%。随着水与乙酸比例的增加，产物中异冰片醇的GC含量和选择性增加，但莰烯的转化率下降。通过添加乙酸乙酯或硫酸钛/硫酸锆形成三元复合催化剂来提高异冰片醇的收率。以硫酸钛、酒石酸、硼酸三元络合物为催化剂时，产物中异冰片醇的GC含量达到55.6%。在无溶剂条件下，扁桃酸-硼酸可以催化莰烯的水合反应，产物中异龙脑的GC含量达到26.1%，异龙脑的选择性为55.9%。 HCA-硼酸复合催化剂可以使用乙酸水溶液作为原料，这也有利于催化剂的重复利用。

  DOI：

  10.3390/molecules28041875

文献信息

• [EN] SUBSTITUTED QUINAZOLINES AS FUNGICIDES<br/>[FR] QUINAZOLINES SUBSTITUÉES, UTILISÉES EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010136475A1

  公开（公告）日：2010-12-02

  The present invention relates to a compound of formula (I) wherein wherein the substituents have the definitions as defined in claim 1or a salt or a N-oxide thereof, their use and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

  本发明涉及一种具有如下式（I）的化合物，其中取代基具有权利要求1中定义的定义，或其盐或N-氧化物，它们的用途以及用于控制和/或预防植物中微生物感染，特别是真菌感染的方法，以及制备这些化合物的方法。
• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。
• FUNGICIDAL ISOXAZOLIDINES
  申请人：TSENG CHI-PING

  公开号：US20090270407A1

  公开（公告）日：2009-10-29

  Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, wherein A, B, D, R 1 , R 2 , R 3 , X and m are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  公开的是Formula 1的化合物，包括所有的几何和立体异构体、N-氧化物和盐， 其中 A、B、D、R 1 、R 2 、R 3 、X和m如披露中所定义。 还公开了含有Formula 1化合物的组合物，以及用于控制由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。
• Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
  作者：Farhad Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah、Ali-Reza Aliakbar

  DOI：10.1016/j.crci.2013.01.018

  日期：2014.2

  eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively

  摘要 以稻壳 (RiH) 为原料，开发了一种温和、高效、环保的方案，用于化学选择性保护苄基和伯和受阻较小的仲脂肪醇和酚作为三甲基甲硅烷基醚以及不同类型的胺作为 N-叔丁基氨基甲酸酯。催化剂。该试剂还能够催化醇、酚、硫醇和胺与乙酸酐的乙酰化反应。该方法的显着特点是后处理简单、反应时间相对较短、收率高、成本低、催化剂的可用性和可重复使用性是该方法的显着特点，可被认为是保护醇、酚的最佳和通用方法之一、硫醇和胺。此外，
• [EN] FUNGICIDAL PYRIDAZINES<br/>[FR] PYRIDAZINES FONGICIDES
  申请人：DU PONT

  公开号：WO2010036553A1

  公开（公告）日：2010-04-01

  Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, wherein R1, R2, R3, R4, X, Y and m are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  公开的是Formula 1的化合物，包括所有的几何和立体异构体、N-氧化物和盐，其中R1、R2、R3、R4、X、Y和m如披露中所定义。还公开了含有Formula 1化合物的组合物，以及用于控制由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。