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人参炔醇 | 81203-57-8

中文名称
人参炔醇
中文别名
——
英文名称
(3S,9Z)-heptadeca-1,9-diene-4,6-diyn-3-ol
英文别名
(3S,9Z)-1,9-heptadecadiene-4,6-diyn-3-ol;(3S)-falcarinol;(S)-Falcarinol;(Z)-falcarinol;(S)-Panaxynol;3S-falcarinol;Panaxynol;(3S,9Z)-heptadeca-1,9-dien-4,6-diyn-3-ol
人参炔醇化学式
CAS
81203-57-8
化学式
C17H24O
mdl
——
分子量
244.377
InChiKey
UGJAEDFOKNAMQD-MQNTZWLQSA-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:
    370.6±42.0 °C(Predicted)
  • 密度:
    0.931±0.06 g/cm3(Predicted)
  • 溶解度:
    溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
  • 保留指数:
    1997

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:建立专利气道。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,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……。预见并治疗癫痫发作……。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。对于误食,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……。/刺激性材料/
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,考虑进行口咽或鼻咽气管插管以控制气道。在上呼吸道梗阻的第一个迹象出现时,可能需要早期插管。使用气囊阀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”,最低流速。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。 ... 使用地西泮(安定)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:从据报道会导致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是falcarinol,即庚癸-1,9(Z)-二烯-4,6-二炔-3-醇。同时测试了三种与falcarinol密切相关的聚乙炔,分别为falcarindiol、falcarinone和dehydrofalcarinone。在一位38岁的女性园艺工作者身上,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/实验和化学调查发现,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物。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)之外,这是第三个发现这些聚乙炔类致敏剂的五加科植物。Falcarinol和didehydrofalcarinol也出现在常春藤的加那利群岛亚种(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也能在所有人中引起强烈反应。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)

SDS

SDS:4ca134831475f1e2171d3d6f071e9789
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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:
    (R)-methoxytrifluoromethylphenylacetyl chloride人参炔醇吡啶4-二甲氨基吡啶 作用下, 以75%的产率得到[(3S,9Z)-heptadeca-1,9-dien-4,6-diyn-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
    参考文献:
    名称:
    Cytotoxic Falcarinol Oxylipins from Dendropanax arboreus
    摘要:
    The crude organic extract of Dendropanax arboreus was selected as a candidate for bioassay-guided fractionation on the basis of its relatively selective cytotoxicity to a subset of cell lines within the National Cancer Institute's disease-oriented in vitro tumor-screening panel. The major compound responsible for the in vitro cytotoxicity was falcarinol (1). Several other known compounds were isolated and found to be cytotoxic, including dehydrofalcarinol (2), a diynene (3), falcarindiol (4), and dehydrofalcarindiol (5). In addition, two novel polyacetylenes, dendroarboreols A (6) and B (7), were isolated and characterized by standard and inverse-detected NMR methods. Compounds were selected from this series for absolute stereochemical determination using the modified Mosher method and preliminary in vivo evaluation using a LOX melanoma mouse xenograft model.
    DOI:
    10.1021/np960224o
  • 作为产物:
    描述:
    2-癸炔-1-醇 在 Lindlar's catalyst 喹啉四氯化碳氢氧化钾copper(l) iodide四丁基氯化铵氢气potassium carbonate三苯基膦 作用下, 以 乙醇N,N-二甲基甲酰胺 为溶剂, 反应 39.25h, 生成 人参炔醇
    参考文献:
    名称:
    Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction
    摘要:
    Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.
    DOI:
    10.1021/jo020073w
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文献信息

  • [EN] HUMANIZED ANTI-TN-MUC1 ANTIBODIES AND THEIR CONJUGATES<br/>[FR] ANTICORPS ANTI-TN-MUC1 HUMANISÉS ET LEURS CONJUGUÉS
    申请人:CANCER REC TECH LTD
    公开号:WO2015159076A1
    公开(公告)日:2015-10-22
    Humanized anti-Tn-MUC1 antibodies and conjugates thereof. Conjugates comprising pyrrolobenzodiazepines (PBDs) having a labile protecting group in the form of a linker to the antibody are described.
    人性化抗Tn-MUC1抗体及其结合物。描述了包含吡咯苯并二氮杂环己烷(PBDs)的结合物,其具有作为连接物的不稳定保护基团。
  • [EN] METHOD AND MOLECULES<br/>[FR] MÉTHODE ET MOLÉCULES
    申请人:MEDIMMUNE LLC
    公开号:WO2018218093A1
    公开(公告)日:2018-11-29
    The present invention provides a bioconjugation method and compounds for use therein. The bioconjugation method comprises the step of conjugating a biological molecule containing a first unsaturated functional group with a payload comprising a second unsaturated functional group, wherein the first and second unsaturated functional groups are complementary to each other such that conjugation is a reaction of said functional groups via a Diels-Alder reaction which forms a cyclohexene ring.
    本发明提供了一种生物共轭方法和其中使用的化合物。该生物共轭方法包括将含有第一不饱和官能团的生物分子与包含第二不饱和官能团的荷载物质共轭的步骤,其中第一和第二不饱和官能团互补,使得通过 Diels-Alder 反应发生官能团之间的结合,形成一个环己烯环。
  • TASTE MODULATOR AND METHOD OF USE THEREOF
    申请人:International Flavors & Fragrances Inc.
    公开号:US20150104398A1
    公开(公告)日:2015-04-16
    The present invention is directed to a novel taste-masking composition comprising a taste-masking effective amount of an Angelica root extract, which shows unexpected effectiveness in reducing an undesirable taste in a food product (e.g., a beverage, broth, or whole grain food product), a dental product, an oral hygiene product or a medicinal product.
    本发明涉及一种新型掩味组合物,包括一定量的Angelica根提取物,该提取物在减少食品产品(例如饮料、汤、全谷食品产品)、口腔产品、口腔卫生产品或药品中的不良味道方面表现出意想不到的有效性。
  • [EN] SITE-SPECIFIC ANTIBODY-DRUG CONJUGATES<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT SITE-SPÉCIFIQUES
    申请人:VAN BERKEL PATRICIUS HENDRIKUS CORNELIS
    公开号:WO2016166299A1
    公开(公告)日:2016-10-20
    Site-specific antibody-drug conjugates are described, in particular conjugates comprising an antibody which binds PSMA, and which comprises an amino acid substitution of an interchain cysteine residue by an amino acid that is not cysteine and pyrrolobenzodiazepines (PBDs) having a labile protecting group in the form of a linker. The site of conjugation, along with modification of the antiobody moiety, allows for improved safety and efficacy of the ADC.
    特定于位点的抗体药物偶联物被描述,特别是包括结合PSMA的抗体的偶联物,其包括通过将链间半胱氨酸残基替换为非半胱氨酸和具有易裂解保护基的吡咯并苯二氮䓬啉(PBDs)的氨基酸的偶联物。偶联位置以及抗体部分的修饰,可以提高ADC的安全性和有效性。
  • [EN] SITE-SPECIFIC ANTIBODY-DRUG CONJUGATES<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT SPÉCIFIQUES À UN SITE
    申请人:VAN BERKEL PATRICIUS HENDRIKUS CORNELIS
    公开号:WO2016166341A1
    公开(公告)日:2016-10-20
    Site-specific antibody-drug conjugates are described, in particular conjugates comprising an antibody, which binds CD25 and comprises an amino acid substitution of an interchain cysteine residue by an amino acid that is not cysteine, and pyrrolobenzodiazepines (PBDs) having a labile protecting group in the form of a linker. The site of conjugation, along with modification of the antibody moiety, allows for improved safety and efficacy of the ADC.
    描述了特定于位点的抗体药物共轭物,特别是包括一种抗体的共轭物,该抗体结合CD25并包括通过氨基酸替换使一个链间半胱氨酸残基成为非半胱氨酸的氨基酸,以及具有以连接物形式的易降解保护基团的吡咯苯并二氮杂环己烯酮(PBDs)。结合位点以及抗体部分的修饰,可提高ADC的安全性和有效性。
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