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falcarinol | 21852-80-2

中文名称
——
中文别名
——
英文名称
falcarinol
英文别名
(+/-)-heptadeca-1,9E-diene-4,6-diyn-3-ol;cis-(-)-Heptadeca-1,9-dien-4,6-diyn-3-ol;(9E)-heptadeca-1,9-dien-4,6-diyn-3-ol
falcarinol化学式
CAS
21852-80-2;81203-57-8
化学式
C17H24O
mdl
——
分子量
244.377
InChiKey
UGJAEDFOKNAMQD-ZHACJKMWSA-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

  • 沸点:
    115 °C(Press: 0.02 Torr)
  • 密度:
    0.931±0.06 g/cm3(Predicted)
  • 溶解度:
    DMF:20mg/mL; DMSO:30mg/mL; DMSO:PBS (pH 7.2) (1:1):0.5 mg/ml;乙醇:20mg/mL
  • LogP:
    6.257 (est)
  • 保留指数:
    2000

计算性质

  • 辛醇/水分配系数(LogP):
    5.5
  • 重原子数:
    18
  • 可旋转键数:
    9
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.53
  • 拓扑面积:
    20.2
  • 氢给体数:
    1
  • 氢受体数:
    1

ADMET

毒理性
  • 副作用
皮肤致敏剂 - 一种可以诱导皮肤产生过敏反应的制剂。
Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 解毒与急救
基本治疗:建立通畅气道。如有必要,进行吸痰。鼓励患者深呼吸。观察呼吸不足的迹象,如有必要,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,并在必要时进行治疗……。监测休克,并在必要时进行治疗……。预期可能出现癫痫,并在必要时进行治疗……。对于眼睛污染,立即用水冲洗眼睛。在转运过程中,用生理盐水连续冲洗每只眼睛……。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……。/刺激物/
Basic Treatment: Establish a patent airway. Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. 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 normal saline 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 ... . /Irritating materials/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
高级治疗:对于昏迷、严重肺水肿或呼吸停止的患者,考虑进行口对口或鼻对鼻气管插管以控制气道。在上呼吸道阻塞的第一个迹象出现时,可能需要早期插管。使用气囊面罩装置的正压通气技术可能有益。监测心率和必要时治疗心律失常...。开始静脉输液,使用D5W/SRP:“保持开放”,最低流量/。如果出现低血容量的迹象,使用乳酸钠林格液。注意液体过载的迹象。考虑使用药物治疗肺水肿...。用安定(Valium)治疗癫痫...使用丙美卡因氢氯化物协助眼部冲洗...。/刺激性材料/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation at the first sign of upper airway obstruction may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
人类暴露研究/皮肤:从据报道能引起过敏性接触性皮炎的植物Schefflera arboricola中,分离并确定了过敏性接触性皮炎的诱因为falcarinol,即十七烷-1,9-(Z)-二烯-4,6-二炔-3-醇。同时测试了与falcarinol密切相关的三种聚乙炔,分别为falcarindiol、falcarinone和dehydrofalcarinone。在一位38岁的女性苗圃工人身上,falcarinol引起了过敏性接触性皮炎,而falcarindiol、falcarinone和dehydrofalcarinone则没有引起。
/HUMAN EXPOSURE STUDIES/ Skin: From the plant Schefflera arboricola, which has been reported to cause allergic contact dermatitis, ... the elicitor of allergic contact dermatitis /was isolated and determined to be/ falcarinol, heptadeca-1,9(Z)-diene-4,6-diyne-3-ol. Three polyacetylenes closely related to falcarinol, namely falcarindiol, falcarinone and dehydrofalcarinone were tested simultaneously. Falcarinol, but not falcarindiol, falcarinone and dehydrofalcarinone, elicited allergic contact dermatitis in a 38-year-old female plant-nursery worker.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
人类暴露研究/实验和化学研究揭示了常春藤(Hedera helix susp. helix)含有3种化合物,这些化合物是强烈的刺激物和中等程度的致敏剂。其中只有2种成分,falcarinol和didehydrofalcarinol,在整年中都存在于植物中。除了人参(Panax ginseng)和鹅掌柴(Schefflera arboricola)外,这是第三个发现这些聚乙炔基致敏剂的五加科植物。Falcarinol和didehydrofalcarinol也出现在常春藤变种Hedera helix subsp. canariensis中。对4名患者进行了贴片测试。即使在低浓度(0.03%)下,主要过敏原falcarinol也能在所有受试者中引起强烈的反应。其中一名作者在调查期间变得敏感。
/HUMAN EXPOSURE STUDIES/ Experimental and chemical investigations revealed that common ivy (Hedera helix susp. helix) contains 3 compounds which are powerful irritants and moderate sensitizers. Only 2 of these constituents, falcarinol and didehydrofalcarinol, are present in the plant during the whole year. Besides Panax ginseng and Schefflera arboricola, this is the third species of the Araliaceae in which these polyacetylenic sensitizers have been found. Falcarinol and didehydrofalcarinol also occur in Hedera helix subsp. canariensis. 4 patients have been patch tested. Even in low concentrations (0.03%), the main allergen falcarinol elicited strong reactions in all of them. One of the authors became sensitized during the investigations.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 海关编码:
    2905290000

SDS

SDS:dd1733d21e7fa37d755446af289e9af1
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制备方法与用途

概述

镰叶芹醇(Panaxynol)又被称为人参炔醇(Falcarinol),是一种聚乙炔醇类化合物。它主要存在于多种植物中,尤其是三七。研究表明,镰叶芹醇具有广泛的生物活性。

提取分离

应用超临界CO2萃取技术可以有效提取和纯化三七中的脂溶性成分,得到高纯度的镰叶芹醇(纯度>98%,得率0.077%)。这一方法显著提高了产品的质量和效率,为进一步开发提供了广阔的空间。

生物活性 抗肿瘤作用
  • 镰叶芹醇能够抑制非小细胞肺癌干细胞形成球体的能力,并通过诱导凋亡抑制其存活。
  • 对正常细胞无明显影响。
神经保护作用
  • 促进神经元突触生长,为神经系统提供营养和保护。
  • 提高cAMP水平,对缺氧缺糖和过氧化氢引起的损伤有显著的保护效果,但对谷氨酸引发的损伤无效。这种作用可能在治疗阿尔茨海默病中发挥作用。
其他活性
  • 抑制Hsp90(热休克蛋白90),是一种口服活性的抗肿瘤药物。
  • 对大鼠心功能、主动脉平滑肌细胞增殖等方面也表现出一定的影响。
参考文献
  1. 段贤春, 汪永忠, 居靖等. 镰叶芹醇研究进展[J]. 安徽医药,2008, 12(1):1-3.
  2. 王泽剑, 陈红专, 陆阳. 镰叶芹醇对神经细胞的营养和保护作用[J]. 中国药学杂志,2005, 40(14):1073-1076.
  3. 李海清, 刘蓉, 赵倩倩等. 镰叶芹醇对大鼠心功能的影响[J]. 中国医学创新,2016, 13(17):1-7.
  4. 蒋丽萍, 聂宝明, 卢慧敏等. 镰叶芹醇对大鼠主动脉平滑肌细胞增殖的抑制作用及机制[J]. 中国药理学通报,2005, 21(11):1313-1319.
  5. 段贤春, 汪永忠, 周安等. 三七中镰叶芹醇的提取、分离和鉴定[J]. 安徽中医药大学学报,2008, 27(2):50-52.
生物活性

Falcarinol (Panaxynol) 是一种天然的、口服活性的 Hsp90 抑制剂,具有有限的毒性,并诱导细胞凋亡。

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

反应信息

  • 作为反应物:
    描述:
    falcarinol间氯过氧苯甲酸 作用下, 以 氯仿 为溶剂, 反应 24.0h, 以36%的产率得到trans-panaxydol
    参考文献:
    名称:
    Synthesis of Ginseng Diyne Analogues and Their Antiproliferative Activity against L1210 Cells
    摘要:
    Some analogues of Ginseng diyne were synthesized and tested for antiproliferative activity against L1210 cells. The epoxy moiety of panaxydol, isolated from the root of Panax ginseng, proved to be in the cis-form on comparison with synthetic specimens. Analysis of structure-activity relationship revealed that the presence of the heptadec-1-ene-4,6-diyn-3-ol moiety in the structure of the analogues was essential for their antiproliferative activity and that the epoxy and alkyl groups in the structure contributed to enhancement of the antiproliferative activity.
    DOI:
    10.1002/(sici)1521-4184(19994)332:4<133::aid-ardp133>3.0.co;2-g
  • 作为产物:
    描述:
    反式-1-溴-2-癸烯rac-hept-1-ene-4,6-diyn-3-ol乙基溴化镁 、 copper dichloride 作用下, 生成 falcarinol
    参考文献:
    名称:
    Synthesis of Ginseng Diyne Analogues and Their Antiproliferative Activity against L1210 Cells
    摘要:
    Some analogues of Ginseng diyne were synthesized and tested for antiproliferative activity against L1210 cells. The epoxy moiety of panaxydol, isolated from the root of Panax ginseng, proved to be in the cis-form on comparison with synthetic specimens. Analysis of structure-activity relationship revealed that the presence of the heptadec-1-ene-4,6-diyn-3-ol moiety in the structure of the analogues was essential for their antiproliferative activity and that the epoxy and alkyl groups in the structure contributed to enhancement of the antiproliferative activity.
    DOI:
    10.1002/(sici)1521-4184(19994)332:4<133::aid-ardp133>3.0.co;2-g
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文献信息

  • A short synthesis of (+) and (−)-falcarinol
    作者:Noel P. McLaughlin、Eibhlín Butler、Paul Evans、Nigel P. Brunton、Anastasios Koidis、Dilip K. Rai
    DOI:10.1016/j.tet.2010.10.049
    日期:2010.12
    A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess
    报道了双炔天然产物falcarinol 1的短而实用的合成。该方法依赖于双-三甲基甲硅烷基丁二炔10的替代功能化。这可以在一锅中实现,但是,更常规地获得了更好的产量。脂肪酶介导的外消旋加合物在有机溶剂中的酶促动力学拆分,得到(+)- 1的对映体过量为97%。在水性条件下用外消旋的3-乙酰氧基福尔卡诺醇11进行的类似过程得到(-)- 1。用Dess-Martin高碘烷氧化1可以得到falcarinone 2。
  • COMPOSITIONS AND METHODS COMPRISING PANAX SPECIES
    申请人:Herbalscience Singapore Pte. Ltd.
    公开号:EP1937289A2
    公开(公告)日:2008-07-02
  • EP1937289A4
    申请人:——
    公开号:EP1937289A4
    公开(公告)日:2009-07-29
  • Methods and compositions comprising Panax species
    申请人:Gow T. Robert
    公开号:US20070065526A1
    公开(公告)日:2007-03-22
    The present invention comprises compositions comprising essential oils, ginsenosides, and polysaccharides. The present invention comprises methods comprising sequential solvent extraction and polymer absorbent purification to obtain fractions comprising essential oils, ginsenosides, and polysaccharides. The compositions of the present invention may be used in forms such as tablets, gel caps, or fast-dissolve tablets for use as dietary supplements or pharmaceutical compositions. The compositions of the present invention may be used for treatment of cardiovascular diseases, neurodegenerative diseases, inflammatory diseases, hepatic disorders, viral diseases, and cancer.
  • US9163307B2
    申请人:——
    公开号:US9163307B2
    公开(公告)日:2015-10-20
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