Rhein 大黄酸

CAS 478-43-3 MFCD00009618

化学结构图

478-43-3
SMILES: O=C(O)c1cc(O)c2c(c1)C(=O)c1cccc(O)c1C2=O

化学属性

Mol. FormulaC15H8O6
Mol. Weight284.22
Melting Point>300°C
Solubility<0.1 G/100 ML AT 17 ºC
TSCANo
Density1.687
Appearance 为咖啡色针晶,升华后为黄色针晶。熔点 321-322℃,水溶性<;0.1g/100mL
Boiling Point597.8°C at 760 mmHg

别名和识别编码

Chemical NameRhein
MDL NumberMFCD00009618
CAS Number478-43-3
Synonym 1 1,8-DIHYDROXYANTHRAQUINONE-3-CARBOXYLIC ACID 2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo- 4,5-DIHYDROXYANTHRAQUINONE-2-CARBOXYLIC ACID 4,5-Dihydroxy-2-anthraquinonecarboxylic Acid 4,5-Dihydroxyanthraquinone-2-carboxylic acid 4,5-Dihydroxyanthraquinone-2-carboxylic acid, 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, Rhubarb yellow 4,5-Dihydroxyanthraquinone-2-carboxylic acid; 1,8-Dihydroxy-3-carboxyanthraquinone; 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid; Rhubarb yellow; Cassic acid 9,10-DIHYDRO-4,5-DIHYDROXY-9,10-DIOXO-2-ANTHRACENECARBOXYLIC ACID 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroicaci CASSIC ACID Monorhein NSC 38629 RHEIN RHEIN90%,95% RHUBARB YELLOW Rheic acid Rhein Rhein (
Beilstein Registry Number2222155
EC Number207-521-4
PubChem Substance ID10168
Reaxys-RN2222155
Merck Number8176
Chemical Name Translation大黄酸
InChIKeyFCDLCPWAQCPTKC-UHFFFAOYSA-N
LabNetwork Molecule IDLN00189427
InChIInChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
Canonical SMILESO=C(C(C=C1C2=O)=CC(O)=C1C(C3=C2C=CC=C3O)=O)O
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分类

  • {SNA} Building Blocks, C13 to C42+, Carbonyl Compounds, Carboxylic Acids, Chemical Synthesis, Organic Building Blocks
  • {
  • {SNA} Alphabetical Index of Phytochemical Standards, Analytical Standards, Cassia, N - R, Phytochemical Standards, Phytochemical Standards by Plant Genus, Polygonum, Quinones, Rheum, 分析/色谱
  • {SNA} Aloe Ve
  • {SNA} Bioactive Small Molecules, Building Blocks, C13 to C42+, Carbonyl Compounds, Carboxylic Acids, Cell Biology, Chemical Synthesis, Organic Building Blocks, R
  • {SNA} Aloe Vera, Ant

产品应用

  • 具抗炎,抗骨关节炎,及抗癌活性。它降低IL -1β的产生和分泌,诱导一氧化氮合成酶的活性,磷酸化的c - Jun和c - Jun氨基末端激酶(JNK)的磷酸化。

相关文献及参考

  • [2]. Hou ML, et al. The Drug-Drug Effects of Rhein on the Pharmacokinetics and Pharmacodynamics of Clozapine in Rat Brain Extracellular Fluid by In Vivo Microdialysis. J Pharmacol Exp Ther. 2015 Oct;355(1):125-34.
  • [3]. Yan-Xi Zhou, et al. Rhein: A Review of Pharmacological Activities. Evid Based Complement Alternat Med. 2015; 2015: 578107.
  • Merck: 14,8176
  • Merck: 14,8176 Beilstein:10(4)4088
  • [1]. Xiaowen Chen, et al. Toll-like receptor 4 is involved in a protective effect of rhein on immunoglobulin A nephropathy. Indian J Pharmacol. 2015 Jan-Feb; 47(1): 27–33.
  • [1]. Xiaowen Chen, et al. Toll-like receptor 4 is involved in a protective effect of rhein on immunoglobulin A nephropathy. Indian J Pharmacol. 2015 Jan-Feb; 47(1): 27–33.
  • [2]. Hou ML, et al. The Drug-Drug Effects of Rhein on the Pharmacokinetics and Pharmacodynamics of Clozapine in Rat Brain Extracellular Fluid by In Vivo Microdialysis. J Pharmacol Exp Ther. 2015 Oct;355(1):1

安全信息

GHS Symbol
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。
  • 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。
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • 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
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 Germany2
Signal word Warning
RTECSCA9516000
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xi
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;
  • 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       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >5 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   PHTOEH Pharmacology and Toxicology (Copenhagen).  (Munksgaard International
   Pub., POB 2148, DK-1016 Copenhagen K, Denmark)  V.60-    1987-
   Volume(issue)/page/year: 61,153,1987

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >25 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   PHTOEH Pharmacology and Toxicology (Copenhagen).  (Munksgaard International
   Pub., POB 2148, DK-1016 Copenhagen K, Denmark)  V.60-    1987-
   Volume(issue)/page/year: 61,153,1987

其他信息

  • 用途一:医药中间体、保健食品原料
  • 理化性质:大黄酸的化学名称为“1,8-二羟基蒽醌-3-羧酸”。分子式C15H8O6。分子量284.21。升华得黄色针状晶体。熔点321~322℃,分解温度330℃,UVλmax(甲醇)229、258、435nm。溶于碱及吡啶,微溶于醇、醚、苯、氯仿、石油醚,不溶于水。能形成红色钾盐、桃红色钠盐,与氢氧化钙及氢氧化钡形成红色沉淀。制法:从大黄酸二乙酸酯水解而得。用途:目前临床上治风湿病药物中常含有大黄酸。 大黄酸是从蓼科植物掌叶中药大黄(Rheum palmatum L.)的根中提取的一种蒽醌类化合物,具有抗菌、抗癌、导泻、利尿的作用,大黄中大黄酸、芦荟大黄素及大黄素的含量情况如下表: 以上信息由Chemicalbook的彤彤编辑整理。
  • 大黄酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/06/21 338990010 大黄酸 Rhein 90% 1 GR 14562元 2010/06/21 338992500 大黄酸 Rhein 90% 250 MG 4459元 2010/06/21 338990500 大黄酸 Rhein 90% 50 MG 1223元
  • Sigma Aldrich:478-43-3(sigmaaldrich)
  • MSDS 信息:1,8-Dihydroxy-3-carboxyanthraquinone(478-43-3).msds
  • Acros Organics:大黄酸 Rhein, 90%(478-43-3)
  • MOL 文件:478-43-3.mol
  • 药理作用:大黄酸含有大黄酚、大黄素、芦荟大黄素、大黄酸、番泻甙等化学成分。 大黄酸和大黄素均具有抗肿瘤的作用,尤其是对黑色素瘤有很强的抑制作用,对乳腺癌和艾氏腹水癌也有一定抑制作用。对小鼠乳腺癌进行瘤内给药,对癌组织有明显的破坏作用。5mg/kg的大黄酸及大黄素对小鼠黑色素瘤的抑制率分别为76%及73%。大黄素对酪氨酸酶有显著的竞争性抑制作用,这种抑制作用可能是大黄抗黑色素瘤的作用机制之一。大黄素浓度在10μg/ml 对人肺癌A-549细胞的分裂有抑制作用,对肺癌A-549细胞DNA的生物合成有明显抑制作用。大黄的粗提物皮下注射,对小鼠肉瘤S37有抑制作用。大黄酸对艾氏腹水癌抑制率为15%,对小鼠肉瘤 S180抑制率为21%。大黄的热水提取物对小鼠肉瘤 S180抑制率为48.8%。 大黄酸对小鼠白血病P388有抑制作用。从大黄中提取到大黄酸、大黄素和芦荟大黄素。这3种蒽醌衍生物均不同程度地减少肿瘤鼠的腹水量和癌细胞数,其中以大黄酸的作用较明显,芦荟大黄素较差,基本上与延长存活期呈平行关系。大黄酸和大黄素对 DNA、RNA和蛋白质的生物合成的抑制作用较强,而芦荟大黄素的抑制作用较弱。

系列性分类


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