(1R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-OL | 124-76-5

• 物质功能分类: 香精与香料 - 合成香料 - 醇类香料
• 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: (1R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-OL
• CAS: 124-76-5
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: DTGKSKDOIYIVQL-KTOWXAHTSA-N

物化性质

• 熔点：
  212-214 °C (subl.)(lit.)
• 沸点：
  214°C
• 密度：
  0.8389 (rough estimate)
• 闪点：
  200 °F
• 溶解度：
  在甲醇中几乎透明
• LogP：
  2.32-2.92 at 20-25℃
• 物理描述：
  DryPowder; Liquid; OtherSolid
• 颜色/状态：
  White solid
• 气味：
  Camphor odor
• 蒸汽压力：
  3.53X10-2 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.
• 气味阈值：
  Detection: 2.5 to 16 ppb

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

毒理性

• 相互作用

多巴胺（DA）引起的氧化应激可能在帕金森病（PD）的发病机制中发挥重要作用。(+/-)异冰片是一种单萜醇，存在于许多药用植物的精油中，是一种已知的抗氧化剂。在本研究中，我们调查了异冰片对6-羟基多巴胺（6-OHDA）诱导的人神经母细胞瘤SH-SY5Y细胞死亡的神经保护作用。用异冰片预处理SH-SY5Y细胞显著减少了6-OHDA诱导的活性氧种（ROS）的产生和6-OHDA诱导的细胞内钙的增加。此外，异冰片处理逆转了6-OHDA诱导的凋亡。异冰片保护了细胞免受6-OHDA诱导的胱天蛋白酶-3活性增加和细胞色素C从线粒体向细胞质转位的影响。异冰片防止了6-OHDA降低Bax/Bcl-2比例。我们还观察到异冰片降低了c-Jun N末端激酶的激活，并诱导了6-OHDA抑制的蛋白激酶C（PKC）的激活。我们的结果表明，异冰片的保护功能取决于其抗氧化潜力，并且强烈建议异冰片可能是一种有效的治疗与氧化应激相关的神经退行性疾病的药物。

Oxidative stress caused by dopamine (DA) may play an important role in the pathogenesis of Parkinson's disease (PD). (+/-) Isoborneol is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and is a known antioxidant. In this study, we investigated the neuroprotective effect of isoborneol against 6-hydroxydopamine (6-OHDA)-induced cell death in human neuroblastoma SH-SY5Y cells. Pretreatment of SH-SY5Y cells with isoborneol significantly reduced 6-OHDA-induced generation of reactive oxygen species (ROS) and 6-OHDA-induced increases in intracellular calcium. Furthermore, apoptosis induced by 6-OHDA was reversed by isoborneol treatment. Isoborneol protected against 6-OHDA-induced increases in caspase-3 activity and cytochrome C translocation into the cytosol from mitochondria. Isoborneol prevented 6-OHDA from decreasing the Bax/Bcl-2 ratio. We also observed that isoborneol decreased the activation of c-Jun N-terminal kinase and induced activation of protein kinase C (PKC) which had been suppressed by 6-OHDA. Our results indicate that the protective function of isoborneol is dependent upon its antioxidant potential and strongly suggest that isoborneol may be an effective treatment for neurodegenerative diseases associated with oxidative stress.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：异冰片是一种白色固体。它被用作食品和饮料中的香料成分。它也用于香水制造和化学酯的制备。人体研究：在一项人类最大量测试中，没有观察到10%异冰片在凡士林中引起的敏感性反应。在0.016%至0.08%的浓度范围内，异冰片对人细胞系测试时没有表现出显著的细胞毒性。动物研究：在0.016%至0.08%的浓度范围内，异冰片对猴细胞系测试时没有表现出显著的细胞毒性。交叉参考化学品l-冰片和异冰片醋酸酯进行了遗传毒性、重复剂量毒性、发育和生殖毒性的评估。在针对大鼠进行的异冰片醋酸酯13周亚慢性毒性研究中，确定无观察到效应水平（NOEL）为15 mg/kg/天，基于增加的尿细胞排泄。在亲代生殖毒性的无观察到有害效应水平（NOAEL）确定为300 mg/kg/天，针对异冰片醋酸酯。l-冰片在Ames试验中不是致突变剂。异冰片在Bluescreen分析中评估了其遗传毒性潜力，发现在有和没有代谢激活的情况下对遗传毒性和细胞毒性为阴性。

IDENTIFICATION AND USE: Isoborneol is a white solid. It is used as a flavor ingredient in food and beverages. It is also used in perfumery and in preparation of chemical esters.HUMAN STUDIES: In a human maximization test, no reactions indicative of sensitization were observed with 10% isoborneol in petrolatum. Isoborneol did not exhibit significant cytotoxicity at concentrations ranging between 0.016% and 0.08% when tested against human cell lines. ANIMAL STUDIES: Isoborneol did not exhibit significant cytotoxicity at concentrations ranging between 0.016% and 0.08% when tested against monkey cell lines. Read across chemicals l-borneol and isobornyl acetate were evaluated for genotoxicity, repeated dose toxicity, developmental and reproductive toxicity. In the13-week subchronic toxicity study for isobornyl acetate conducted in rats the NOEL was determined to be 15 mg/kg/day, based on increased urinary cell excretion.The NOAEL for reproductive toxicity in the parental generation was determined to be 300 mg/kg/day for isobornyl acetate. l-borneol was not mutagenic in the Ames test. Isoborneol, was assessed for genotoxic potential in the Bluescreen assay and was found negative for genotoxicity and cytotoxicity in the presence and absence of metabolic activation.

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、球囊阀面罩设备或口袋面罩，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，让患者向前倾或将其置于左侧（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。寻求医疗帮助。 /毒物A和B/

/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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/

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，如有需要，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，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在转运过程中，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，如果患者能吞咽、有强烈的干呕反射且不流口水，则冲洗口腔并给予5毫升/千克，最多200毫升的水进行稀释……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 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 ... . /Poisons A and B/

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……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。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%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。注意液体过载的迹象……。用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/毒物A和B/

/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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as 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. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

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 labeled 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
• 危险等级：
  4.1
• 危险品标志：
  F,Xi
• 安全说明：
  S24/25
• 危险类别码：
  R11
• WGK Germany：
  2
• 海关编码：
  2906199090
• 危险品运输编号：
  25kgs
• RTECS号：
  NP7300000
• 包装等级：
  II
• 危险类别：
  4.1
• 危险性防范说明：
  P210,P240,P241,P264,P280,P302+P352
• 危险性描述：
  H228,H315

制备方法与用途

异龙脑简介

异龙脑是一种林业化工产品，又名异莰醇，性质与樟脑相近。它主要用于日化产品中的香料，并作为防腐剂使用。白色异龙脑的外观和性质与樟脑相似，成本较低，具有广阔的市场应用前景。

毒性

根据GRAS（FEMA，FDA，§1.72．515，2000）规定，异龙脑被归类为安全物质。

使用限量

• 饮料：6.2 mg/kg
• 冰淇淋：23 mg/kg
• 糖果：11 mg/kg
• 焙烤制品：8.3 mg/kg
• 胶姆糖：0.80 mg/kg

食品添加剂最大允许使用量及残留标准

• 添加剂中文名称：异龙脑
• 允许使用该种添加剂的食品中文名称：食品
• 添加剂功能：食品用香料，用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量

化学性质

异龙脑是一种白色晶体，具有类似樟脑的气味。它能溶于乙醇、乙醚、氯仿和石油醚中而不浑浊。

用途

• 香料：用于日化产品
• 防腐剂
• 食用香料

生产方法

异龙脑由一蒎烯经氯化氢加成进行分子重排生成莰烯，再水化、重排而成。

反应信息

• 作为产物：
  描述：

  camphor 在 RuCl(CO)(CH₂C₆H₃(CH₃)(P(C₆H₅)2))(C₅H₄N(CH₂NH₂)) sodium hydroxide 、 异丙醇 作用下， 反应 5.0h， 生成 (1R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-OL
  参考文献：
  名称：

  [EN] RUTHENIUM COMPLEXES, THEIR PREPARATION AND USE AS CATALYSTS
  [FR] COMPLEXES DE RUTHENIUM, PREPARATION ET UTILISATION DE CEUX-CI COMME CATALYSEURS

  摘要：

  公开号：

  WO2005051965A3

文献信息

• Neue Bindemittelkombinationen für hochbeständige Kunststofflacke
  申请人：Bayer MaterialScience AG

  公开号：EP1502926A1

  公开（公告）日：2005-02-02

  Die vorliegende Erfindung betrifft neue Bindemittelkombinationen aus Polyisocyanaten, speziellen Lacton-basierenden Polyolen und Polyesterpolyolen sowie deren Verwendung zur Herstellung von Überzügen, vorzugsweise auf Kunststoffen.

  本发明涉及多异氰酸酯、特殊内酯基多元醇和聚酯多元醇的新型粘合剂组合，以及它们在涂料生产中的应用，最好是在塑料上的应用。
• Vapor-phase corrosion inhibitors and method of preparing same
  申请人：——

  公开号：US20030031583A1

  公开（公告）日：2003-02-13

  Substance combinations which contain (1) an inorganic salt of nitrous acid, (2) a water-insoluble polysubstituted phenol, (3) an aliphatic ester of a dihydroxybenzoic acid, and (4) a tocopherol plus optionally (5) a suitable water vapor-volatile bicyclic terpene or an aliphatically substituted naphthalene which promotes sublimation of the components present in the respective substance combination, especially in air at a relatively high atmospheric humidity, and the use of such substance combinations as vapor phase corrosion inhibitors in packaging or in storage in closed spaces for protection of the conventional metals for use such as iron, chromium, nickel, tin, zinc, aluminum, copper and their alloys against atmospheric corrosion are described.

  含有(1)亚硝酸的无机盐，(2)不溶于水的多代苯酚，(3)二羟基苯甲酸的脂肪族酯，(4)生育酚，以及(5)适当的水蒸气挥发性双环萜烯或脂肪族取代的萘的物质组合，可促进相应物质组合中存在的成分升华、特别是在大气湿度相对较高的空气中，以及将此类物质组合作为气相腐蚀抑制剂用于包装或封闭空间的储存，以保护铁、铬、镍、锡、锌、铝、铜等传统金属及其合金免受大气腐蚀。
• Water-dilutable polyesters with cyclic imide structure
  申请人：——

  公开号：US20040063852A1

  公开（公告）日：2004-04-01

  The present invention relates to novel polyesterpolyols with cyclic imide structure and to their use in coating compositions.

  本发明涉及具有环状亚胺结构的新型聚酯多元醇及其在涂料组合物中的应用。
• Water-dilutable polyesters with cyclic imide and isocyanurate structure
  申请人：——

  公开号：US20040077817A1

  公开（公告）日：2004-04-22

  The present invention relates to novel polyesterpolyols with cyclic imide and isocyanurate structure and to their use in coating compositions.

  本发明涉及具有环状亚胺和异氰脲酸酯结构的新型聚酯多元醇及其在涂料组合物中的应用。
• New binder combinations for highly resistant plastic paints
  申请人：Wamprecht Christian

  公开号：US20050027095A1

  公开（公告）日：2005-02-03

  Binder combinations containing polyisocyanates, special lactone-based polyols and polyester polyols and to their use for producing coatings, preferably on plastics.

  含有多异氰酸酯、特殊内酯基多元醇和聚酯多元醇的粘合剂组合，以及它们在生产涂料（最好是塑料涂料）中的用途。