borneol | 16725-71-6

• 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: borneol
• 英文别名: isoborneol；(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 16725-71-6；124-76-5；507-70-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: DTGKSKDOIYIVQL-OYNCUSHFSA-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：
  Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes.
• 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
• 保留指数：
  1164

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

• 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：在一项人体最大量测试中，没有观察到10%异冰片在凡士林中引起敏感化的反应。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。交叉参考化学物质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，根据增加的尿细胞排泄，确定无观察到有害效应水平（NOEL）为15 mg/kg/天。在亲代生殖毒性研究中，异冰片醋酸酯的无观察到有害效应水平（NOAEL）确定为300 mg/kg/天。l-冰片在 Ames 测试中不是致突变物。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，异冰片对遗传毒性和细胞毒性均为阴性。

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

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

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

• 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，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，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，有强烈的干呕反射，并且不流口水，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……。/毒物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)

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 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

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

• 作为反应物：
  描述：

  borneol 在 双氧水