468-28-0

• 常用中文名：蛇床酮
• 常用英文名：Lupulone
• CAS号：468-28-0
• 分子式：C₂₆H₃₈O₄
• 分子量：414.58
• 相关类别： 信号通路 抗感染 细菌
• 发布时间：2018-06-21 09:35:26
• 更新时间：2024-01-09 11:33:46
• 羽扇豆酮是一种来自啤酒花植物H.lupulus的β酸,具有多种生物活性,包括抗菌、抗氧化和抗癌特性[1][2][3]。

名称

• 中文名: 蛇床酮
• 英文名: 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• 中文别名: 蛇麻酮
• 英文别名: 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-; β-Lupulic acid; B'-Acid; EINECS 207-405-3; 3,5-Dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one; β-Bitter acid; b-Lupulic Acid; 3,5-Dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methyl-2-buten-1-yl)-2,4-cyclohexadien-1-one; b-Bitter Acid; Lupulon; Lupulone; 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-

物化性质

• 密度: 1.0±0.1 g/cm3
• 沸点: 498.4±45.0 °C at 760 mmHg
• 熔点: 93ºC
• 分子式: C₂₆H₃₈O₄
• 分子量: 414.58
• 闪点: 269.3±25.2 °C
• 精确质量: 414.277008
• PSA: 74.60000
• LogP: 8.77
• 蒸汽压: 0.0±2.9 mmHg at 25°C
• 折射率: 1.530

生物活性

• 描述: 羽扇豆酮是一种来自啤酒花植物H.lupulus的β酸,具有多种生物活性,包括抗菌、抗氧化和抗癌特性[1][2][3]。
• 相关类别:
  研究领域 >> 癌症
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 参考文献:

  [1]. Tagashira M, et al. Antioxidative activity of hop bitter acids and their analogues. Biosci Biotechnol Biochem. 1995 Apr;59(4):740-2.

  [2]. Lamy V, et al. Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells. Apoptosis 13(10), 1232-1242 (2008).

  [3]. Bocquet L, et al. Phenolic Compounds from Humulus lupulus as Natural Antimicrobial Products: New Weapons in the Fight against Methicillin Resistant Staphylococcus aureus, Leishmania mexicana and Trypanosoma brucei Strains. Molecules. 2019 Mar 14;24(6):1024.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : OK5950000 CHEMICAL NAME : Lupulone CAS REGISTRY NUMBER : 468-28-0 LAST UPDATED : 199309 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C26-H38-O4 MOLECULAR WEIGHT : 414.64 WISWESSER LINE NOTATION : L6V BHJ B2UY1&1 B2UY1&1 CQ DV1Y1&1 EQ F2UY1&1 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 : 100 mg/kg TOXIC EFFECTS : Behavioral - ataxia Lungs, Thorax, or Respiration - cyanosis REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 17,79,1967 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 330 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold REFERENCE : FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 8,281,1949 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 525 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - excitement Lungs, Thorax, or Respiration - other changes REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 17,79,1967 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 600 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),39,1982 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 600 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold REFERENCE : FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 8,281,1949 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 1 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 82,1,1950 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 130 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold REFERENCE : FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 8,281,1949

安全

• 危害码 (欧洲): T: Toxic;
• 风险声明 (欧洲): R25
• 危险品运输编码: UN 2811
• 包装等级: III
• 危险类别: 6.1(b)