Emodin 大黄素

CAS 518-82-1 MFCD00001207

化学结构图

518-82-1
SMILES: Cc1cc(O)c2c(c1)C(=O)c1cc(O)cc(O)c1C2=O

化学属性

Mol. FormulaC15H10O5
Mol. Weight270
Density1.583
Melting Point255
SolubilitySoluble in ethanol, sodium carbonate solution, DMSO (1 mg/ml), aqueous alkali, 1eq. NaOH (100 mM), ammonium hydroxide (10 mg/ml), ether, chloroform, benzene , and THF. Insoluble in water.
Appearance 橙色针状结晶。熔点256-257℃（259-260℃）。溶于乙醇，略溶于乙醚、氯仿、苯，不溶于水。溶于苛性碱水溶液、碳本酸钠水溶液，氨溶液中显樱红色。 powder
StabilityLight,Air sensitive
Boiling Point

别名和识别编码

Chemical NameEmodin, from Rhubarb root and rhizome, content ≥90%, NIFDC traceable
CAS Number518-82-1
Synonym 1 1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione 1,3,8-Trihydroxy-6-methylanthraquinone, 6-Methyl-1,3,8-trihydroxyanthraquinone, Emodol, Frangula-emodin 1,3,8-Tri­hydroxy-6-methyl­anthra­quinone, 6-Methyl-1,3,8-tri­hydroxy­anthra­quinone, Emodol, Frangula-emodin 1,3,8-trihydroxy-6-methyl-anthraquinon 1,3,8-三羥-6-甲蒽醌 4,5,7-TRIHYDROXY-2-METHYL ANTHRAQUINONE 6-METHYL-1,3,8-TRIHYDROXYANTHROQUINONE 6-Methyl-1,3,8-trihydroxyanthraquinone 8-三羟基-6-甲基蒽醌 9,10-ANTHRACENEDIONE, 1,3,8-TRIHYDROXY-6-METHYL- 9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl- ALOE EMODIN Archin Casanthranol EMODIN EMODOL Emodin Emodin, Frangula Emodin, Rheum Frangula Emodin Frangulic Acid Peristim Persian Berry Lake Rheum Emodin {} {} {
MDL NumberMFCD00001207
Beilstein Registry Number1888141
EC Number208-258-8
PubChem Substance ID3220
Reaxys-RN1888141
Merck Number3561
Chemical Name Translation大黄素
Wiswesser Line NotationL C666 BV IVJ DQ FQ L1 NQ
LabNetwork Molecule IDLN00220710
InChIInChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3
Canonical SMILESO=C1C2=C(C=C(C)C=C2O)C(C3=CC(O)=CC(O)=C31)=O
信息真实价格透明    资金保障    专业采购外包团队在线服务   
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分类

  • {SNA} Anti-Proliferative Agents,
  • Anti-Proliferative Agents, Antitumor Agents, Bioactive Small Molecules, Cancer Research, Casein Kinase (CK), Cell Biology, Cell Signaling and Neuroscience, E, Glycosides, Including Glucosinolates,
  • {S
  • {SNA} Anti-Proliferative Agents, Antitumor Agents, Bioactive Small Molecules, Casein Kinase (CK), Cell Signaling and Neuroscience, E, Glycosides, Including Glucosinolates, Kinase/Phosphatase Biology, Nutrition Research, Phytochemicals by Chemical Classification, Protein Kinase Inhibitors, Serine/Threonine Kinase Biology, Serine/Threonine Kinase Inhibitors, 癌症研究, 细胞生物学

产品应用

  • 抑制NF -κB活化及粘附分子的表达。酪蛋白激酶2（CK2的）抑制剂.

相关文献及参考

  • Ba, X., et al., Trypanosoma Cruzi Induces The Reactive Oxygen Species-PARP-1-RelA Pathway For Up-regulation Of Cytokine Expression In Cardiomyocytes. J. Thorac. Cardiovasc. Surg. 285 , 11596-606, (2010)
  • Merck: 14,3561 Beilstein:8(4)3575
  • Zhang, et al., Tyrosine kinase inhibitor emodin suppresses growth of HER-2/neu-overexpressing breast cancer cells in athymic mice and sensitizes these cells to the inhibitory effect of paclitaxel. Clin. Cancer Res. 5 , 343-353, (1999) 摘要
  • Kumar, et al., Emodin (3-methyl-1,6,8-trihydroxyanthraquinone) inhibits TNF-induced NF-kappaB activation, IkappaB degradation, and expression of cell surface adhesion proteins in human vascular endothelial cells. Oncogene 17 , 913-918, (1998) 摘要
  • Pan, X., et al.: Biochem. Eng. J., 5, 173
  • Merck: 14,3561

安全信息

GHS Symbol
RTECSCB7920600
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P264+P265
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P302+P350
  • P302+P352
  • P302+P352+P332+P313+P362+P364
  • P304+P340
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P319
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P332+P313
  • P332+P317
  • P337+P313
  • P337+P317
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P362+P364
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
WGK Germany3
Signal word Warning {} {} {} {} {} {} {} {} {} {} {} {TCI}
Hazard Codes Xi
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Storage condition 2-8°C 储存温度 2-8°C 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 35 mg/kg
TOXIC EFFECTS :
   Gastrointestinal - other changes
REFERENCE :
   JAFCAU Journal of Agricultural and Food Chemistry.  (American Chemical Soc.,
   Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC
   20037)  V.1-    1953-  Volume(issue)/page/year: 27,1342,1979

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - hamster Lung
DOSE/DURATION           : 10 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 240,1,1990

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 50 ug/plate
REFERENCE :
   BCSTB5 Biochemical Society Transactions.  (Biochemical Soc. Book Depot, POB
   32, Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1973-
   Volume(issue)/page/year: 5,1489,

TYPE OF TEST            : Unscheduled DNA synthesis
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 10 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 240,1,1990

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 2 ug/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 188,161,1987

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 5 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 269,27,1992

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - mouse Fibroblast
DOSE/DURATION           : 3 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 240,1,1990

{hazard_

UN Number
Packing Group

其他信息

  • 理化性质:大黄素学名“1，3，8-三羟基-6-甲基蒽醌”。分子式C15H10O5。分子量270.24。以游离和苷形式存在于蓼科植物掌叶大黄、大黄、唐古特大黄的根茎及根中。橘黄色结晶。熔点256～257℃。能真空升华(1,600帕)。溶于乙醇、氢氧化钠、碳酸钠、氨的水溶液中，微溶于乙醚、氯仿、四氯化碳、苯，几乎不溶于水。其三醋酸酯为黄色结晶，熔点197℃。其3-甲醚 (亦称大黄素甲醚)为深红色针状结晶，熔点207℃。可由植物提取或通过化学合成。 芦荟大黄素为芦荟精油主要组分之一，以游离状态存在于芦荟中，或以配糖体存在于大黄、番泻叶及芦荟中。 以上信息由Chemicalbook的彤彤编辑整理。
  • 利尿作用:大黄酸、大黄素有明显的利尿作用，服药后2～4小时尿量增加达到高峰，同时Na+、K+的排出量也达到高峰。芦荟大黄素和大黄酚作用较弱。作用机理是由于大黄酸、大黄素对肾髓质Na+-K+-ATP酶有抑制作用。肾小管内Na+的
  • 抗肿瘤作用:药理研究发现，大黄蒽醌衍生物、大黄酸、大黄素和芦荟大黄素均有明显的抗癌作用，较敏感者有黑色素瘤、P388白血病和艾氏腹水癌。大黄多糖对肉瘤S180有明显抑制作用。大黄素浓度10μg/mL，可使人肺癌A-549细胞的最大生长密度减少，分裂指数降低，氚标法胸腺嘧啶核苷的掺入量明显减少。细胞的DNA含量明显降低。并发现此药可使 G1和S期细胞相对增加，G2+M期和异倍体细胞相对减少，组方图的峰值左旋，出现在较低通道上。表明大黄素对人体肺癌A-549细胞的分裂有明显的抑制作用。大黄的抗肿瘤作用机理目前认为是抑制了癌细胞的呼吸和DNA的生物合成。也有人认为大黄酸、大黄素对癌细胞有直接破坏作用。
  • {Chemical
  • 方法一:大黄素广泛存在于植物性泻药，如大黄的根茎、鼠李的树皮和根皮、决明的种子中。从大黄的根茎可提取大黄素。通过合成也可以制备大黄素，例如以2-甲基蒽醌，或以3，5-二硝基苯酐和间甲酚为原料，者可以制得大黄素。
  • 用途一:该品可用作泻药，大黄素虽有泻下活性，但由于体内易被氧化破坏，实际上泻下作用很弱，如与糖结合成苷类，则可发挥泻下作用。大黄素-1-O-β-D-葡萄糖苷和大黄素-8-O-β-D-葡萄糖苷者是大黄素
  • 溶于乙醇，略溶于乙醚、氯仿、苯，不溶于水。溶于苛性碱水溶液、碳本酸钠水溶液，氨溶液中显樱红色。
  • TCI Shanghai:大黄素 Emodin,>;96.0%(LC)(518-82-1)
  • 大黄的化学成分:从各种大黄中已分离并鉴定的化合物达130余种，包括蒽醌及其甙类、蒽酮类、双蒽酮及其甙类、茋类及其甙和没食子酸酯、萘类衍生物、色满酮及其甙类、苯基丁酮类、鞣质类等。其中蒽醌类为其重要的代表性成分。游离蒽醌主要有：大黄酸(Rhei
  • 存储注意事项:光敏感;空气敏感
  • 大黄:大黄为蓼科大黄属植物掌叶大黄Rheum palmatum L.、唐古特大黄Rheum tanguticum Maxim. ex Balf. 或药用大黄Rheum officinale Baill. 的干燥根茎。唐古特大黄与掌叶大黄的主要区别为叶片深3裂，呈细长羽片状。花序分枝紧密，常直立，紧贴于茎上。药用大黄与以上两种大黄的主要区别是叶浅裂，浅裂片呈大齿形或宽三角形，花较大，黄白色，花蕾椭圆形果枝开展。大黄属全世界约60种，中国约50种。 形态：大黄为多年生高大草本，高2m左右。根茎及根肥厚，黄褐色。茎直立，光滑无毛，中空。基生叶有肉质粗状的长柄，约与叶片等长，叶片宽卵形或近圆形，径可达40cm，掌状半裂，裂片3～5(-7)，每1裂片有时再羽裂或具粗齿，基部略呈心脏形；茎生叶较小，具短柄；托叶鞘状，膜质，密生短柔毛。 生境与分布：生于山地林缘或草坡，野生或栽培。分布于陕西、甘肃东南部、青海、四川西部、云南西北部及西藏东部。 栽培：宜于凉爽湿润气候，耐寒，怕高温多湿;以土层深厚、富含腐殖质的砂质壤土及石灰质壤土种植为好。 采集：9～10月选择生长3年以上的植株，挖取根茎，切除茎叶、支根、刮去粗皮及顶芽，风干、烘干或切片晒干。 图1为大黄图片。
  • Sigma Aldrich:518-82-1(sigmaaldrich)
  • 用途一:该品可用作泻药，大黄素虽有泻下活性，但由于体内易被氧化破坏，实际上泻下作用很弱，如与糖结合成苷类

系列性分类

  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Chemical Classification - Nutrition Research
  4. Glycosides, Including Glucosinolates - Phytochemicals by Chemical Classification
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Ketones - Carbonyl Compounds
  6. C15 to C38 - Ketones
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Life Sciences Standards - Chromatography
  5. Phytopharma Standards - Life Sciences Standards
  6. Alphabetical - Phytopharma Standards
  7. E - H - Alphabetical
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Kinase/Phosphatase Biology - Cell Signaling and Neuroscience
  5. Serine/Threonine Kinase Biology - Kinase/Phosphatase Biology
  6. Serine/Threonine Kinase Inhibitors - Serine/Threonine Kinase Biology
  7. Casein Kinase (CK) - Serine/Threonine Kinase Inhibitors
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Kinase/Phosphatase Biology - Cell Signaling and Neuroscience
  5. Serine/Threonine Kinase Biology - Kinase/Phosphatase Biology
  6. Serine/Threonine Kinase Inhibitors - Serine/Threonine Kinase Biology
  7. Casein Kinase (CK) - Serine/Threonine Kinase Inhibitors
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Chemicals by Class 化学分类法
  4. Anthraquinones
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Ketones 酮
  6. C13 to C14
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Protein Kinases and Phosphatases
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Kinase/Phosphatase Biology
  5. Protein Kinase Activators
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Peptides and Proteins
  5. Kinases and Phosphatases
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Proteins and Derivatives
  4. Proteins for Cell Biology
  5. Kinases and Phosphatases
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Kinase/Phosphatase Biology
  5. Serine/Threonine Kinase Biology
  6. Serine/Threonine Kinase Inhibitors
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Peptides and Proteins
  5. Proteins for Cell Biology
  6. Immune System Proteins

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