6659-45-6

• 常用中文名：二氢鱼藤酮
• 常用英文名：Dihydrorotenone
• CAS号：6659-45-6
• 分子式：C₂₃H₂₄O₆
• 分子量：396.433
• 相关类别： 信号通路 细胞凋亡 细胞凋亡
• 发布时间：2018-05-22 08:00:00
• 更新时间：2025-08-20 13:51:49
• Dihydrorotenone 是一种天然杀虫剂,是一种线粒体 (mitochondrial) 抑制剂。Dihydrorotenone 可能诱发帕金森综合症。Dihydrorotenone 通过触发内质网应激并激活 p38 信号通路来诱导人浆细胞凋亡 (apoptosis)

名称

• 中文名: 二氢鱼藤酮
• 英文名: Dihydrorotenone (VAN)
• 英文别名: 1',2'-dihydrorotenone; 1-Dihydrorotenon; Furo[2',3':7,8][1]benzopyrano[2,3-c][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethyl)-, (2R,6aS,12aS)-; Dihydrorotenone; 6'.7'-Dihydro-rotenon; (2R,6aS,12aS)-2-Isopropyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one; 6',7'-dihydrorotenone

物化性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 553.9±50.0 °C at 760 mmHg
• 熔点: 216 °C
• 分子式: C₂₃H₂₄O₆
• 分子量: 396.433
• 闪点: 241.6±30.2 °C
• 精确质量: 396.157288
• PSA: 63.22000
• LogP: 4.82
• 外观性状: 粉末
• 蒸汽压: 0.0±1.5 mmHg at 25°C
• 折射率: 1.580
• 储存条件: 2-8°C，密封，干燥

生物活性

• 描述: Dihydrorotenone 是一种天然杀虫剂,是一种线粒体 (mitochondrial) 抑制剂。Dihydrorotenone 可能诱发帕金森综合症。Dihydrorotenone 通过触发内质网应激并激活 p38 信号通路来诱导人浆细胞凋亡 (apoptosis)
• 相关类别:
  信号通路 >> 细胞凋亡 >> 细胞凋亡
  信号通路 >> 代谢酶/蛋白酶 >> 线粒体代谢
  研究领域 >> 神经疾病
• 参考文献:

  [1]. Zhang J, et al. The natural pesticide dihydrorotenone induces human plasma cell apoptosis by triggering endoplasmic reticulum stress and activating p38 signaling pathway. PLoS One. 2013 Jul 26;8(7):e69911.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : DJ2623100 CHEMICAL NAME : (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6a-al phah)-one, 1,2,12,12a-alpha-tetrahydro- 2-alpha-isopropyl-8,9-dimethoxy- CAS REGISTRY NUMBER : 6659-45-6 LAST UPDATED : 199512 DATA ITEMS CITED : 4 MOLECULAR FORMULA : C23-H24-O6 MOLECULAR WEIGHT : 396.47 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2500 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - other changes REFERENCE : JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 42,364,1953 TYPE OF TEST : LD - Lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : >2 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : IECHAD Industrial and Engineering Chemistry. (Washington, DC) V.15-62, 1923-70. For publisher information, see CHMTBL. Volume(issue)/page/year: 29,429,1937 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 150 mg/kg TOXIC EFFECTS : Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes REFERENCE : IECHAD Industrial and Engineering Chemistry. (Washington, DC) V.15-62, 1923-70. For publisher information, see CHMTBL. Volume(issue)/page/year: 29,429,1937 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 4616 mg/kg/57W-C TOXIC EFFECTS : Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death REFERENCE : JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 42,364,1953

合成路线

83-79-4 ~91% 6659-45-6

文献：O'Neil, James P.; VanBrocklin, Henry F.; Morimoto, Hiromi; Williams, Philip G. Journal of Labelled Compounds and Radiopharmaceuticals, 1997 , vol. 39, # 3 p. 215 - 221

34487-52-0 ~% 6659-45-6

文献：Carson, David; Crombie, Leslie; Kilbee, Geoffrey W.; Moffatt, Frank; Whiting, Donald A. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982 , p. 779 - 788

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