isobornyl acetate | 28974-17-6

• 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: isobornyl acetate
• 英文别名: bornyl acetate；Isobornylacetat；(-)-borneol acetate；Pichtosin；Isoborneol, acetate；[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] acetate
• CAS: 28974-17-6
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: KGEKLUUHTZCSIP-FOGDFJRCSA-N

物化性质

• 沸点：
  223.5±0.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)
• 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
• 闪点：
  190 °F (88 °C) /closed cup/
• 溶解度：
  In water 9.721 mg/L at 25 °C (est)
• 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）成异冰片基醇。这种醇将与葡萄糖醛酸结合，并通过尿液排出（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的剂量下出现了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，让患者前倾或置于左侧（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。 /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）。必要时进行吸痰。观察呼吸不足的迹象，必要时协助通气。通过非重复呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时治疗……。监测休克，并在必要时治疗……。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……。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"，最低流量/。如果出现低血容量的迹象，使用0.9%盐水（NS）或乳酸林格氏液（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 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)

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  isobornyl acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.42h， 以96.1%的产率得到isoborneol
  参考文献：
  名称：

  一种乙酸异龙脑酯连续皂化制备异龙脑的方法

  摘要：

  本发明公开了一种乙酸异龙脑酯连续皂化制备异龙脑的方法，以氢氧化钠和乙酸异龙脑酯为原料，经皂化、精馏、分层、水洗、结晶等步骤制备出白色异龙脑晶体。其皂化反应可在振荡流反应器、静态混合器或超声混合器中实现连续操作；反应中加入极性溶剂，使皂化反应在均相中进行，可缩短反应时间，降低反应温度，其乙酸异龙脑酯的转化率在99%以上，产品收率95%以上，说明该方法生产能耗低，产品收率高。

  公开号：

  CN104478666B
• 作为产物：
  描述：

  白樟油 在 吡啶 、 lithium aluminium tetrahydride 作用下， 生成 isobornyl acetate
  参考文献：
  名称：

  Enantioselectivity in the hydrolysis of bicyclic monoterpene acetates with the cultured cells of Nicotiana tabacum

  摘要：

  DOI：

  10.1016/s0031-9422(00)83743-7

文献信息

• Poly(N-vinylimidazole) as an efficient catalyst for acetylation of alcohols, phenols, thiols and amines under solvent-free conditions
  作者：Nader Ghaffari Khaligh

  DOI：10.1039/c2ra21295a

  日期：——

  Poly(N-vinylimidazole) is able to promote instantaneous quantitative acetylation of a variety of functionalized alcohols, phenols, thiols and amines with acetic anhydride at room temperature under solvent-free conditions. This new method consistently has excellent yields and the catalyst can be reused and recovered several times. Furthermore, the reaction can even be carried out on a larger scale.

  聚（N-乙烯基咪唑）能够促进多种功能化醇，酚，硫醇和胺的瞬时定量乙酰化醋酸酐在室温下于无溶剂条件下进行。这种新方法始终具有出色的收率，并且催化剂可以重复使用和回收多次。此外，反应甚至可以更大规模地进行。
• A succinimide-N-sulfonic acid catalyst for acetylation reactions in absence of a solvent
  作者：Farhad SHIRINI、Nader Ghaffari KHALIGH

  DOI：10.1016/s1872-2067(11)60499-3

  日期：2013.4

  Abstract A small amount of succinimide-N-sulfonic acid efficiently catalyzed the acetylation of a variety alcohols, phenols, thiols, amines and aldehydes with acetic anhydride at room temperature under solvent free conditions. This catalyst has the advantages of excellent yields and short reaction times and the reaction can be carried out on a large scale, which makes it potentially useful for industrial

  摘要 在室温、无溶剂条件下，少量的琥珀酰亚胺-N-磺酸可有效催化多种醇类、酚类、硫醇类、胺类和醛类与乙酸酐的乙酰化反应。该催化剂具有收率高、反应时间短等优点，反应可以大规模进行，具有潜在的工业应用价值。
• Baptistella, Lucia Helena B.; Santos, Jose Fernando dos; Ballabio, Karin Cristina, Synthesis, 1989, # 6, p. 436 - 438
  作者：Baptistella, Lucia Helena B.、Santos, Jose Fernando dos、Ballabio, Karin Cristina、Marsaioli, Anita Jocelyne

  DOI：——

  日期：——
• Synthesis and absolute configuration of the antiparasitic furanosesquiterpenes (-)-furodysin and (-)-furodysinin. Camphor as a six-membered ring chiral pool template
  作者：Valerie Vaillancourt、Mohamad R. Agharahimi、Uma N. Sundram、Olivier Richou、D. John Faulkner、Kim F. Albizati

  DOI：10.1021/jo00001a069

  日期：1991.1

  The syntheses of (-)-furodysin ((-)-2a) and (-)-furodysinin ((-)-3a) in four steps starting from (+)-9-bromocamphor (18) has been accomplished, thus establishing the absolute configuration of these and related metabolites. This was made possible by the unexpected exo selectivity in the aldol condensation of camphor-like enolates with aldehydes. This has been found to be a general phenomenon in the camphor system. Further, anionic fragmentation of the C1-C7 bond of camphor derivatives has allowed access to synthetic intermediates containing functionalized six-membered rings, thus opening up avenues from camphor to a new class of chiral pool elements not currently available from chiral pool substances.
• Esterification of camphene over heterogeneous heteropoly acid catalysts: Synthesis of isobornyl carboxylates
  作者：Augusto L.P. de Meireles、Kelly A. da Silva Rocha、Ivan V. Kozhevnikov、Elena V. Gusevskaya

  DOI：10.1016/j.apcata.2011.09.032

  日期：2011.12

  Silica supported H3PW12O40 (PW), the strongest heteropoly acid in the Keggin series, is an active and environmentally friendly solid acid catalyst for liquid-phase esterification of camphene, a renewable biomass-based substrate, with C-2, C-4 and C-6 short-chain fatty acids. The reaction provides isobornyl carboxylates, useful as fragrances, in virtually 100% selectivity and 80-90% yield. The reaction is equilibrium-controlled and occurs under mild conditions with a catalyst turnover number of up to 3000. The use of hydrocarbon solvent prevents PW from leaching to allow easy catalyst recovery. The catalyst can be reused several times without loss of activity and selectivity. (C) 2011 Elsevier B.V. All rights reserved.