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borneol | 16725-71-6

中文名称
——
中文别名
——
英文名称
borneol
英文别名
isoborneol;(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
borneol化学式
CAS
16725-71-6;124-76-5;507-70-0
化学式
C10H18O
mdl
——
分子量
154.252
InChiKey
DTGKSKDOIYIVQL-OYNCUSHFSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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。

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2

反应信息

  • 作为反应物:
    描述:
    borneol双氧水 作用下, 以 为溶剂, 反应 5.5h, 以90%的产率得到
    参考文献:
    名称:
    磺化多孔碳和过氧化氢氧化有机化合物
    摘要:
    摘要 研究了室温下磺化多孔碳和H2O2对有机化合物的氧化反应。烷基和芳基硫化物以极好的收率被氧化成相应的亚砜或砜。仲醇也以良好的产率转化为相应的酯/内酯和醛转化为甲酯。此外,脂肪族叔胺和取代的吡啶被氧化成 N-氧化物。
    DOI:
    10.1016/s1872-2067(10)60127-1
  • 作为产物:
    描述:
    左旋樟脑 在 {PPN}{HCr(CO)5} 、 溶剂黄146 作用下, 以 四氢呋喃 为溶剂, 反应 24.0h, 以5%的产率得到borneol
    参考文献:
    名称:
    阴离子基团 6 过渡金属羰基氢化物作为还原剂。酮、醛和环氧化物
    摘要:
    Etude des proprietes reductrices des complexes suivants: HM(CO) 5 − et cis-HM(CO) 4 P(OCH 3 ) 3 − (M=Cr, W)
    DOI:
    10.1021/ja00294a038
  • 作为试剂:
    描述:
    2-乙酰基吡啶 在 lithium aluminium tetrahydride 、 三氯化铝borneol 作用下, 以 乙醚 为溶剂, 生成 (S)-1-(吡啶-2-基)乙醇(R)-2-(1-羟乙基)吡啶
    参考文献:
    名称:
    Samaddar, Ashis K.; Konar, Samir K.; Nasipuri, Dhanonjoy, Journal of the Chemical Society. Perkin transactions I, 1983, # 7, p. 1449 - 1451
    摘要:
    DOI:
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文献信息

  • The Oxidation of Alcohols in<i>N</i>-Oxyl-Immobilized Silica Gel/Aqueous NaOCl Disperse Systems. A Prominent Access to a Column-Flow System
    作者:Hideo Tanaka、Jingyu Chou、Machiko Mine、Manabu Kuroboshi
    DOI:10.1246/bcsj.77.1745
    日期:2004.9
    The oxidation of alcohols was performed successfully in a disperse system with N-oxyl-adsorbed or immobilized silica gel as a disperse phase and aqueous NaOCl as a disperse medium. In the disperse system, the oxidation of sec-alcohols afforded the corresponding ketones, while prim-alcohols were oxidized to aldehydes and/or carboxylic acids depending on their structures and reaction conditions. The N-oxyl-immobilized silica gel was recovered and repeatedly used without a significant change in the product yields. A column-flow system was also investigated for the oxidation of alcohols by use of a newly devised column packed with the N-oxyl-immobilized silica gel.
    在分散体系中,以N-氧杂-吸附或固定化硅胶为分散相,以水合NaOCl为分散介质,成功地进行了醇的氧化反应。在分散体系中,二级醇被氧化成相应的酮,而一级醇则根据其结构和反应条件的不同被氧化成醛和/或羧酸。N-氧杂固定化硅胶可被回收并在不显著影响产物收率的情况下重复使用。还研究了一种新的柱流系统,该系统采用新设计的填充N-氧杂固定化硅胶的柱子来进行醇的氧化反应。
  • Catalytic oxidation of alcohols with novel non-heme <i>N</i><sub>4</sub>-tetradentate manganese(<scp>ii</scp>) complexes
    作者:Vincent Vermaak、Desmond A. Young、Andrew J. Swarts
    DOI:10.1039/c8dt03808b
    日期:——
    non-heme N4-tetradentate Mn(OTf)2 complexes of the type, [(L)MnOTf2], where L = R,R and S,S enantiomers of BPMCN, its 6-methyl and 6-bromo derivatives as well as the novel ligand BMIMCN (BPMCN = N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-(R,R/S,S)-1,2-diaminocyclohexane, BMIMCN = N,N′-dimethyl-N,N′-bis(1-methyl-2-imidazolemethyl)-(R,R/S,S)-1,2-diaminocyclohexane). Solid state structural analysis of the BMIMCN-ligated
    我们报道了[[L] MnOTf 2 ]类型的一系列新型非血红素N 4-四齿Mn(OTf)2配合物的制备和表征,其中L = BPMCN的R,R和S,S对映体,其6-甲基和6-溴衍生物以及新型配体BMIMCN(BPMCN = N,N'-二甲基-N,N'-双(2-吡啶基甲基)-(R,R / S,S)-1, 2-二氨基环己烷,BMIMCN = N,N'-二甲基-N,N′-双(1-甲基-2-咪唑甲基)-(R,R / S,S)-1,2-二氨基环己烷)。BMIMCN连接的Mn-三氟甲磺酸盐配合物(R,R -C4和S,S -C4)的固态结构分析显示相反的螺旋度,但相同的金属位点可及性。在过氧化氢为氧化剂,乙酸为助催化剂的伯醇和仲醇的催化氧化中,利用了这一特性。配合物R,R -C4和S,S -C4由于BMIMCN配体的供电子特性,苯甲醇具有最高的苯甲醇氧化活性。络合物S,S -C4,对多种伯醇底物显示出高活
  • Silver-Catalyzed Hydrogenation of Ketones under Mild Conditions
    作者:Shengdong Wang、Haiyun Huang、Svetlana Tsareva、Christian Bruneau、Cédric Fischmeister
    DOI:10.1002/adsc.201801523
    日期:2019.2.19
    silver‐catalyzed hydrogenation of ketones using H2 as hydrogen source is reported. Silver nanoparticles are generated from simple silver (I) salts and operate at 25 °C under 20 bar of hydrogen pressure. Various aliphatic and aromatic ketones, including natural products were reduced into the corresponding alcohols in high yields. This silver catalyst allows for the selective hydrogenation of ketones in
    据报道,使用H 2作为氢源,银催化了酮的氢化反应。银纳米粒子由简单的银(I)盐生成,并在25°C和20 bar的氢气压力下运行。各种脂肪族和芳香族酮,包括天然产物,都以高收率被还原成相应的醇。这种银催化剂可以在其他官能团存在的情况下对酮进行选择性加氢。
  • Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
    作者:Farhad Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah、Ali-Reza Aliakbar
    DOI:10.1016/j.crci.2013.01.018
    日期:2014.2
    eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively
    摘要 以稻壳 (RiH) 为原料,开发了一种温和、高效、环保的方案,用于化学选择性保护苄基和伯和受阻较小的仲脂肪醇和酚作为三甲基甲硅烷基醚以及不同类型的胺作为 N-叔丁基氨基甲酸酯。催化剂。该试剂还能够催化醇、酚、硫醇和胺与乙酸酐的乙酰化反应。该方法的显着特点是后处理简单、反应时间相对较短、收率高、成本低、催化剂的可用性和可重复使用性是该方法的显着特点,可被认为是保护醇、酚的最佳和通用方法之一、硫醇和胺。此外,
  • Bis(sym-collidine)bromine(I) hexafluorophosphate as oxidant
    作者:Gérard Rousseau、Sylvie Robin
    DOI:10.1016/s0040-4039(00)01598-7
    日期:2000.11
    Primary and secondary alcohols in solution in methylene chloride are oxidised with bis(sym-collidine)bromine(I) hexafluorophosphate in good yields to the carbonyl compounds. For secondary and tertiary alcohols in which one of the substituents is a 4-methoxyphenyl group the oxidation takes place by cleavage of the phenyl-sp3 carbon bond and formation of bromoanisole and carbonyl compounds.
    在二氯甲烷溶液中伯醇和仲醇被氧化与双(符号-collidine)溴(I)以良好的收率以羰基化合物六氟磷酸盐。对于其中一个取代基是4-甲氧基苯基的仲和叔醇,氧化是通过裂解苯基-sp 3碳键并形成溴茴香醚和羰基化合物来进行的。
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同类化合物

(5β,6α,8α,10α,13α)-6-羟基-15-氧代黄-9(11),16-二烯-18-油酸 (3S,3aR,8aR)-3,8a-二羟基-5-异丙基-3,8-二甲基-2,3,3a,4,5,8a-六氢-1H-天青-6-酮 (2Z)-2-(羟甲基)丁-2-烯酸乙酯 (2S,4aR,6aR,7R,9S,10aS,10bR)-甲基9-(苯甲酰氧基)-2-(呋喃-3-基)-十二烷基-6a,10b-二甲基-4,10-dioxo-1H-苯并[f]异亚甲基-7-羧酸盐 (+)顺式,反式-脱落酸-d6 龙舌兰皂苷乙酯 龙脑香醇酮 龙脑烯醛 龙脑7-O-[Β-D-呋喃芹菜糖基-(1→6)]-Β-D-吡喃葡萄糖苷 龙牙楤木皂甙VII 龙吉甙元 齿孔醇 齐墩果醛 齐墩果酸苄酯 齐墩果酸甲酯 齐墩果酸乙酯 齐墩果酸3-O-alpha-L-吡喃鼠李糖基(1-3)-beta-D-吡喃木糖基(1-3)-alpha-L-吡喃鼠李糖基(1-2)-alpha-L-阿拉伯糖吡喃糖苷 齐墩果酸 beta-D-葡萄糖酯 齐墩果酸 beta-D-吡喃葡萄糖基酯 齐墩果酸 3-乙酸酯 齐墩果酸 3-O-beta-D-葡吡喃糖基 (1→2)-alpha-L-吡喃阿拉伯糖苷 齐墩果酸 齐墩果-12-烯-3b,6b-二醇 齐墩果-12-烯-3,24-二醇 齐墩果-12-烯-3,21,23-三醇,(3b,4b,21a)-(9CI) 齐墩果-12-烯-3,11-二酮 齐墩果-12-烯-2α,3β,28-三醇 齐墩果-12-烯-29-酸,3,22-二羟基-11-羰基-,g-内酯,(3b,20b,22b)- 齐墩果-12-烯-28-酸,3-[(6-脱氧-4-O-b-D-吡喃木糖基-a-L-吡喃鼠李糖基)氧代]-,(3b)-(9CI) 鼠特灵 鼠尾草酸醌 鼠尾草酸 鼠尾草酚酮 鼠尾草苦内脂 黑蚁素 黑蔓醇酯B 黑蔓醇酯A 黑蔓酮酯D 黑海常春藤皂苷A1 黑檀醇 黑果茜草萜 B 黑五味子酸 黏黴酮 黏帚霉酸 黄黄质 黄钟花醌 黄质醛 黄褐毛忍冬皂苷A 黄蝉花素 黄蝉花定

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