(1S,4S)-1,7,7-三甲基双环[2.2.1]庚烷-2-醇 | 791787-82-1

• 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
• 中文名称: (1S,4S)-1,7,7-三甲基双环[2.2.1]庚烷-2-醇
• 英文名称: borneol
• 英文别名: (1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 791787-82-1
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: DTGKSKDOIYIVQL-HKJUDDBKSA-N

物化性质

• 物理描述：
  DryPowder; Liquid; OtherSolid
• 颜色/状态：
  White solid
• 气味：
  Camphor odor
• 沸点：
  Sublimes
• 熔点：
  209.33333333329998 °C
• 溶解度：
  In water, 1.19X10+3 mg/L at 25 °C (est)
• 密度：
  1.10 g/cm cu at 20 °C
• 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

• 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，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，我们探讨了异冰片对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诱导的细胞内钙增加。此外，6-OHDA诱导的凋亡被异冰片处理逆转。异冰片防止了6-OHDA诱导的胱天蛋白酶-3活性增加和细胞色素C从线粒体转移到细胞质。异冰片阻止了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所抑制的蛋白激酶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，并强烈提示异冰片可能是治疗与氧化应激相关的神经退行性疾病的有效治疗方法。

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。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）。必要时进行吸痰。观察呼吸不足的迹象，如有需要，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，并在必要时进行治疗……。监测休克，并在必要时进行治疗……。预期癫痫发作，并在必要时进行治疗……。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……。/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)

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)

反应信息

• 作为反应物：
  描述：

  (1S,4S)-1,7,7-三甲基双环[2.2.1]庚烷-2-醇 在 2,2,6,6-四甲基哌啶氧化物 、 3-[4'-(diacetoxyiodo)phenoxy]-1-propyl-N,N,N-trimethylammonium 4-methylbenzenesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以99%的产率得到左旋樟脑
  参考文献：
  名称：

  TEMPO 介导的醇与离子负载（二乙酰氧基碘）苯的氧化

  摘要：

  在二氯甲烷中催化量的 2,2,6,6-四甲基哌啶-1-氧基（TEMPO）存在下，用新型离子负载（二乙酰氧基碘）苯（IS-DIB）氧化仲醇和伯醇在室温下进行有效地分别以高纯度的良好收率提供相应的酮和醛。通过简单的乙醚萃取反应混合物并随后从萃取物中除去溶剂，很容易实现产物的分离。此外，离子负载的碘苯是目前氧化中由 IS-DIB 衍生的副产物，以良好的收率回收，并且可以重新氧化为 IS-DIB，以便在相同的氧化中重复使用。

  DOI：

  10.1055/s-0031-1290766
• 作为产物：
  描述：

  左旋樟脑 在 lithium aluminium tetrahydride 作用下， 生成 (1S,4S)-1,7,7-三甲基双环[2.2.1]庚烷-2-醇
  参考文献：
  名称：

  高等植物环状单萜生物合成中无环烯丙基焦磷酸酯的互变和环化

  摘要：

  摘要 环状单萜类化合物的生物合成已在几种高等植物的完整植物和无细胞提取物中进行了研究。通过保留所有源自 [2- 14 C,5- 3 H 2 ] 甲羟戊酸和 [1- 14 C,1- 3 H 2 ]香叶基、橙花基和芳樟基焦磷酸酯。无细胞提取物催化香叶基、橙花基和焦磷酸芳樟基相互之间的非氧化还原相互转化。相比之下，在完整植物和无细胞提取物中，焦磷酸芳樟酯掺入环状单萜类化合物的发生优先于橙花酯和香叶基焦磷酸酯掺入。

  DOI：

  10.1016/s0031-9422(00)83738-3

文献信息

• A Convenient and Selective Palladium-Catalyzed Aerobic Oxidation of Alcohols
  作者：Saravanan Gowrisankar、Helfried Neumann、Dirk Gördes、Kerstin Thurow、Haijun Jiao、Matthias Beller

  DOI：10.1002/chem.201302526

  日期：2013.11.18

  An efficient procedure for the oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, with molecular oxygen under ambient conditions has been achieved. By applying catalytic amounts of Pd(OAc)2 in the presence of tertiary phosphine oxides (OPR3) as ligands, a variety of substrates are selectively oxidized without formation of ester byproducts. Spectroscopic investigations

  已经实现了在环境条件下用分子氧将伯醇和仲醇分别氧化为醛和酮的有效方法。通过应用催化量的Pd（OAC）的2在叔膦氧化物（OPR的存在3）作为配体，在各种基材的而不形成酯的副产物的选择性氧化。光谱研究和DFT计算表明，氧化膦配体可稳定活性钯（II）催化剂。
• [Pd(NHC)(PR3)] (NHC = N-heterocyclic carbene) catalysed alcohol oxidation using molecular oxygen
  作者：Václav Jurčík、Thibault E. Schmid、Quentin Dumont、Alexandra M. Z. Slawin、Catherine S. J. Cazin

  DOI：10.1039/c2dt30133d

  日期：——

  [Pd(NHC)(PR3)] complexes quantitatively form [Pd(η2-O2)(NHC)(PR3)] products when submitted to an dioxygen atmosphere. Synthetic details and structural features of these Pd–peroxo complexes are described. The palladium compounds were found to be efficient catalysts in the oxidation of alcohols into corresponding carbonyl compounds using O2 or air as oxidant. Reactions proceed at low catalyst loadings

  一系列[钯（NHC）（PR的3）]配合物定量形式[钯（η 2 -O 2）（NHC）（PR 3）]时提交到双氧气氛产品。描述了这些Pd-过氧配合物的合成细节和结构特征。发现钯化合物是使用O 2或空气作为氧化剂将醇氧化成相应的羰基化合物的有效催化剂。反应在低催化剂负载下与多种醇一起进行。
• (PhCH₂PPh₃)⁺Br₃⁻: A Versatile Reagent for the Preparation, Deprotection, and Oxidation of Trimethylsilyl Ethers
  作者：F. Shirini、G. H. Imanzadeh、A. R. Mousazadeh、I. Mohammadpoor-Baltork、A. R. Aliakbar、M. Abedini

  DOI：10.1080/10426500902915440

  日期：2010.2.23

  Benzyltriphenylphosphonium tribromide (BTPTB), as a stable solid reagent, is easily prepared by the reaction of benzyltriphenylphosphonium bromide with Br2. This reagent can be used as an efficient catalyst for the conversion of alcohols to their corresponding trimethylsilyl ethers (TMS ethers) with hexamethyldisilazane (HMDS). Desilylation of TMS ethers is also catalyzed by BTPTB in MeOH at room temperature

  苄基三苯基三溴化鏻 (BTPTB) 作为一种稳定的固体试剂，很容易通过苄基三苯基溴化鏻与 Br2 反应制备。该试剂可用作将醇与六甲基二硅氮烷 (HMDS) 转化为相应的三甲基甲硅烷基醚 (TMS 醚) 的有效催化剂。TMS 醚的脱甲硅烷基化也在室温下由甲醇中的 BTPTB 以高产率催化。BTPTB 还能够在 MeOH/H2O 混合物中以良好到高产率将 TMS 醚氧化为其相应的羰基化合物。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。
• IBX-TfOH mediated oxidation of alcohols to aldehydes and ketones under mild reaction conditions
  作者：Kamlesh Kumar、Prashant Kumar、Penny Joshi、Diwan S Rawat

  DOI：10.1016/j.tetlet.2020.151749

  日期：2020.4

  secondary alcohols using IBX-TfOH catalytic system in 1,4-dioxane at ambient temperature. The reaction affords quantitative yields of the corresponding carbonyl compounds without the formation of over oxidized products. The present synthetic protocol is compatible with a variety of substrates having arene, heteroarene and alkene functionalities. The developed synthetic protocol can be used for higher scale

  已经开发了一种在环境温度下使用IBX-TfOH催化系统在1,4-二恶烷中氧化伯醇和仲醇的有效，实用且简便的方法。该反应提供定量产率的相应羰基化合物，而不会形成过氧化产物。本合成方案与具有芳烃，杂芳烃和烯烃官能度的多种底物相容。所开发的合成方案可用于更大规模的反应，如通过简单的过滤过程以1 gm规模规模氧化醇以更高的收率所证明。
• Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide
  作者：Amey Palav、Balu Misal、Prerna Ganwir、Purav Badani、Ganesh Chaturbhuj

  DOI：10.1016/j.tetlet.2021.153094

  日期：2021.6

  most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst

  与溴、碘和氟（一种磺酰亚胺试剂）相比，氯是地球上第20 位最丰富的元素，N-氯-N-（苯磺酰基）苯磺酰胺 (NCBSI) 被确定为一种温和的选择性氧化剂。在没有活化的情况下，该试剂被证明可以将伯醇和仲醇以及它们的对称和混合醚氧化成相应的醛和酮。使用可回收的 PS-TEMPO 催化剂，实现了伯醇和仲醇及其醚与给电子取代基的氯化选择性氧化。NCBSI的试剂前体被定量回收，可重复用于合成NCBSI。