Exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl acetate | 5655-61-8

• 物质功能分类: 香精与香料 - 合成香料 - 羧酸及酯类香料
• 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: Exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl acetate
• 英文别名: [(1S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] acetate
• CAS: 5655-61-8；125-12-2；76-49-3
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: KGEKLUUHTZCSIP-RTYFJBAXSA-N

物化性质

• 熔点：
  29°C
• 沸点：
  229-233 °C (lit.)
• 密度：
  0.983 g/mL at 25 °C (lit.)
• 闪点：
  190 °F
• 溶解度：
  0.16克/升
• LogP：
  3.86
• 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
• 蒸汽压力：
  0.107 mm Hg at 25 °C (est)
• 大气OH速率常数：
  1.39e-11 cm3/molecule*sec
• 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。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的剂量下出现少量尿液染色的腹部毛。

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。如果患者呕吐，让患者身体前倾或置于左侧（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. /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）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-松烯作为泡沫浴（Pinimenthol）成分的经皮吸收情况通过使用放射性标记成分在动物身上进行了测量。药代动力学测量显示，所有测试成分在开始经皮吸收后的10分钟内达到最大血药水平。没有成分表现出优先吸收。10分钟经皮吸收后所有成分的血药水平与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

• TSCA：
  Yes
• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R20/21/22
• WGK Germany：
  1
• 海关编码：
  29153900
• 危险品运输编号：
  NA 1993 / PGIII
• 包装等级：
  III
• 危险性防范说明：
  P501,P210,P280,P370+P378,P403+P235
• 危险性描述：
  H302,H227

制备方法与用途

介绍

乙酸异龙脑酯为无色结晶状粉末，具有松香樟脑气味。

制备

乙酸异龙脑酯可由莰烯经烯硫酸催化，加成一分子乙酸，同时发生分子重排而得。工业上一般以松节油为原料，先进行分馏，切取沸程为156-161℃的馏分（主要是α-蒎烯）进行异构化，生成莰烯，再与冰醋酸反应生成乙酸异龙脑酯，经水洗、精馏而得成品。工业产品含乙酸异龙脑酯≥97%，游离酸含量小于0.1%。每吨产品消耗98.5%冰醋酸400kg、松节油1070kg。

含量分析

按酯测定法(OT-18)中方法一测定，所取试样量为1g，计算中的当量因子(e)取98.15。或按气相色谱法(GT-10-4)中用非极性柱方法测定。

毒性

GRAS(FEMA)。

使用限量

FEMA(mg/kg)：软饮料9.6；冷饮12；糖果3.9；焙烤食品9.5；布丁类70。适度为限(FDA§172．515，2000)。

食品添加剂最大允许使用量及最大允许残留量标准

乙酸异龙脑酯作为食品用香料主要用于配制香精，其用量不得超过在GB 2760中的最大允许使用量和最大允许残留量。用于浆果和各种水果型香精（用量极微）。

化学性质

无色结晶状粉末，具有松香樟脑气味。溶于乙醇和乙醚，几乎不溶于甘油和水。

用途

主要用于香料工业，也用作合成樟脑的原料。GB 2760—96规定为允许使用的食用香料，主要用于浆果和各种水果型香精（用量极微）。香料常用作日用化学品如肥皂、爽身粉、花露水、空气喷雾剂等的加香剂。

生产方法

由莰烯、冰醋酸和硫酸共热(50～60℃)后，加水离析并精馏而得。或由异龙脑醇乙酰化而成。