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(-)-borneol | 507-70-0

中文名称
——
中文别名
——
英文名称
(-)-borneol
英文别名
isoborneol;d-borneol;(1R,2R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
(-)-borneol化学式
CAS
507-70-0;124-76-5
化学式
C10H18O
mdl
——
分子量
154.252
InChiKey
DTGKSKDOIYIVQL-VWHDNNRLSA-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 to off-white crystals
  • 气味:
    Piney, camphor-like odor
  • 味道:
    Burning taste somewhat reminiscent of mint
  • 蒸汽压力:
    5.02X10-2 mm Hg at 25 °C
  • 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13周亚慢性毒性研究中,异冰片酯的无观察到有害作用水平(NOEL)确定为15 mg/kg/天,基于尿细胞排出的增加。异冰片酯在亲代生殖毒性的无观察到有害作用水平(NOAEL)确定为300 mg/kg/天。l-冰片在Ames试验中不是致突变剂。异冰片在Bluescreen试验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
  • 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
  • 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,并且强烈表明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)
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
  • 危险品标志:
    F
  • 安全说明:
    S16,S36/37
  • 危险类别码:
    R22,R11
  • WGK Germany:
    2
  • 海关编码:
    2906199090
  • 危险品运输编号:
    UN 1312
  • 危险类别:
    4.1
  • RTECS号:
    DT5095000
  • 包装等级:
    III

SDS

SDS:c0495047a2b478a411676212e2d27658
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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:
    (-)-borneolsilica gelpyridinium chlorochromate 作用下, 以 二氯甲烷 为溶剂, 反应 0.33h, 以87%的产率得到camphor
    参考文献:
    名称:
    Ultrasound in oxochromium(VI)-amine-mediated oxidations - modifications of the Corey-Suggs oxidation for the facile conversion of alcohols to carbonyl compounds
    摘要:
    DOI:
    10.1021/jo00283a041
  • 作为产物:
    描述:
    d-chimgin 在 吡啶sodium hydroxide 作用下, 以 乙醇 为溶剂, 反应 2.0h, 生成 (-)-borneol
    参考文献:
    名称:
    Structures of fersin and fersinin
    摘要:
    DOI:
    10.1007/bf00630400
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文献信息

  • Metal‐Free Tandem Rearrangement/Lactonization: Access to 3,3‐Disubstituted Benzofuran‐2‐(3 <i>H</i> )‐ones
    作者:Micol Santi、Darren M. C. Ould、Jan Wenz、Yashar Soltani、Rebecca L. Melen、Thomas Wirth
    DOI:10.1002/anie.201902985
    日期:2019.6.3
    A novel metal‐free synthesis of 3,3‐disubstituted benzofuran‐2‐(3H)‐ones through reacting α‐aryl‐α‐diazoacetates with triarylboranes is presented. Initially, triarylboranes were successfully investigated in α‐arylations of α‐diazoacetates, however in the presence of a heteroatom in the ortho position, the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center
    通过α-芳基-α-重氮乙酸酯与三芳基硼烷的反应,提出了一种新颖的无金属合成3,3-二取代的苯并呋喃-2-(3 H)-酮的方法。最初,已经成功地研究了三芳基硼烷在α-重氮乙酸酯的α-芳基化中的作用,但是在邻位存在杂原子的情况下,烯醇硼中间体发生分子内重排以形成季中心。该中间体环化以良好的收率提供有价值的3,3-二取代的苯并呋喃酮。
  • The Stereochemical Outcomes - the Isoborneol/Borneol Ratios - in Lithium, Sodium and Potassium/Ammonia Reductions without a Proton Source of the Enantiomers and the Racemate of Camphor Differ Strongly
    作者:Valentin Rautenstrauch
    DOI:10.1002/hlca.19820650143
    日期:1982.2.3
    RS)-borneol] in lithium, sodium and potassium/ammonia reductions without a proton source of the enantiomeric [(1 R, 4 R) or (1 S, 4 S)] and racemic (1RS, 4RS) forms of camphor under the same conditions differ strongly. This explains contradictory reports in the literature and, in the case of the reductions with potassium in which pinacol coupling does not compete, proves that the reductions involve bimolecular
    立体化学结果[比率(1 R,2 R,4 R)-异冰片//(l R,2 S,4 R)异冰片或(1 R,2 S,4 S)-异冰片(l S,2 R,4小号)-borneol和(1个RS,RS 2,RS 4)-isoborneol /(升RS,2 SR,4个RS)-borneol]在锂,钠和钾/氨的减少,而不对映体的质子源[(1- R,4 R)或(1 S,4 S)]和消旋体(1 RS,4 RS)在相同条件下的樟脑形式差异很大。这解释了文献中相互矛盾的报道,并且在与频哪醇偶联不竞争的钾的还原的情况下,证明了还原涉及两个酮基之间,或酮与酮基或酮二价阴离子之间的双分子反应。
  • OPTICAL RESOLVER AND METHOD OF OPTICALLY RESOLVING ALCOHOL WITH THE SAME
    申请人:ZEON CORPORATION
    公开号:EP1364933B1
    公开(公告)日:2007-10-03
  • Enantioselective metal complex catalysis. 6. Rhodium catalysts for asymmetric hydrosilylation based on chiral phosphites
    作者:E. Yu. Zhorov、K. N. Gavrilov、V. A. Pavlov、A. T. Teleshev、L. S. Gorshkova、�. E. Nifant'ev、E. I. Klabunovskii
    DOI:10.1007/bf00961341
    日期:1991.5
    A study has been made of the asymmetric hydrosilylation of acetophenone by diphenylsilane under the influence of rhodium complexes with chiral phosphites. The enantioselective nature of the reaction depends on the phosphite structure, the acetophenone/rhodium and ligand/rhodium ratios, and the temperature. The maximum optical yield (24%) is attained on the complex [Rh(COD)Cl]2/(S, S)-2-ethoxy-4,5-dicarbisopropoxy-1,3-2-dioxophospholane.
  • PELED M.; GINSBURG D., TETRAHEDRON, 1981, 37, NO 1, 161-165
    作者:PELED M.、 GINSBURG D.
    DOI:——
    日期:——
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