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   
信息真实价格透明    资金保障    专业采购外包团队在线服务   
品牌质保精细包装    现货库存    一流品牌服务   

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


相关产品推荐