9,​10-​Anthracenedione, 1,​8-​dihydroxy-​3-​(hydroxymethyl)​- 1,8-二羟基-3-羟甲基蒽醌

CAS 481-72-1 MFCD00017373

化学结构图

481-72-1
SMILES: O=C1c2cccc(O)c2C(=O)c2c(O)cc(CO)cc21

化学属性

Mol. FormulaC15H10O5
Mol. Weight270.24
Density1.592
Melting Point223-224°C
Stability对热敏感

别名和识别编码

Chemical Name9,​10-​Anthracenedione, 1,​8-​dihydroxy-​3-​(hydroxymethyl)​-
CAS Number481-72-1
Synonym Aloe emodin {Chemicalbook} 1,8-Dihydroxy-3-hydroxymethyl anthroquinone 1,8-二羟基-3-羟甲基蒽醌;芦荟泻素 3-Hydroxymethylchrysazine 9,10-ANTHRACENEDIONE,1,8-DIHYDROXY-3-(HYDROXYMETHYL)- ALLYLPYRUVATE ALOE EMODIN hplc ALOE-EMODIN Aloe Emodin Aloe emodin (Diacerein Impurity) {} {JNK} 1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone, 3-Hydroxymethylchrysazine {} {} {TRC} 1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione {} {} {} {Chemicalbook} 1,8-DIHYDROXY-3-(HYDROXYMETHYL)-9,10-ANTHRACENEDIONE {} {} {} {} {} {} {} {} {} {} {} {} {AL {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00017373
PubChem Substance ID10207
Beilstein Registry Number2059062
EC Number207-571-7
Chemical Name Translation1,8-二羟基-3-羟甲基蒽醌
Reaxys-RN2059062
Merck Number306
Wiswesser Line NotationL C666 BV IVJ DQ F1Q NQ
LabNetwork Molecule IDLN00221557
InChIInChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2
Canonical SMILESO=C1C2=C(C=CC=C2O)C(C3=CC(CO)=CC(O)=C13)=O
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分类

  • {SNA} Aloe Vera, Anti-Proliferative Agents, Antitumor Agents, Glycosides, Including Glucosinolates, Nutrition Research, Other Biochemical, Phytochemicals by Chemical Classification, Phytochemicals by Plant (Food/Spice/Herb), 癌症研究, 细胞生物学
  • A - D, Aloe, Alphabetical, Analytical Standards, Analytical/Chromatography, Cassia, Chromatography, Life Sciences Standards, Organic Acids and Esters, Phytopharma Standards, Polygonum, Rhamnus, Rheum, Standards by Plant Genus, Substance Classification
  • {SNA} Aloe Vera,
  • {SNA} Aloe Vera,

产品应用

  • 泻药/泻剂化合物;内源性乙酰胆碱的释放增加了肠道平滑肌收缩。遗传毒性和致突变性似乎是由芦荟大黄素由于抑制拓扑异构酶II活性

相关文献及参考

  • Merck 14 ,306
  • Merck: 14,306
  • Hung, K., et al.: J. Exp. Med., 188, 2357
  • Mueller, S.O., and Stopper, H., Characterization of the genotoxicity of anthraquinones in mammalian cells. Biochim. Biophys. Acta 1428 , 406-414, (1999) 摘要
  • Jing, X., et al., Induction of apoptosis in hepatocellular carcinoma cell lines by emodin. Jpn. J. Cancer Res. 93 , 874-882, (2002) 摘要

安全信息

WGK Germany3
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。
  • 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+P352
  • P302+P352+P332+P313+P362+P364
  • P304+P340
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P332+P313
  • 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
  • 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
Hazard Codes Xi
RTECSCB6712200
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Signal word Warning
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;
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 {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {TCI} 0-10°C 储存温度 2-8°C
TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 18750 ug/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 367,123,1996

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            : 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

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

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 55500 nmol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 371,165,1996

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 10 ug/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/yea

其他信息

  • MOL 文件:481-72-1.mol
  • 易溶于热乙醇,在苯及乙醚中呈黄色,在氨水和硫酸中呈绯红色,属蒽醌类化合物,在酸性溶液中被还原则生成蒽酚及其互变异构体的蒽酮。
  • 大黄:大黄为常用中药。始载于《神农本草经》,列为下品。历代本草均有记载。大黄为蓼科植物掌叶大黄、唐古特大黄或药用大黄Rheum officinale Baill的干燥根及根茎。主产于四川、甘肃、青海等地。大黄具有泻热通肠、凉血解毒、逐瘀通经的功效,用于实热便秘,积滞腹痛,泻痢不爽,湿热黄疸,血热吐衄,目赤,咽肿,肠痈腹痛,痈肿疔疮,瘀血闭经,跌打损伤。外治水火烫伤,上消化道出血等。可生用或酒炙、酒蒸或炒炭。 大黄对多数革兰阳性细菌和某些革兰阴性细菌在试管内均有抑菌作用,有效成分主要是蒽醌类衍生物,其中以芦荟大黄素、大黄素及大黄酸作用最好。 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。 图1为药用大黄Rheum officinale Baill.
  • 外观性质:橙色针状结晶(由甲苯中)。易溶于热乙醇,在苯及乙醚中呈黄色,在氨水和硫酸中呈绯红色,属蒽醌类化合物,在酸性溶液中被还原则生成蒽酚及其互变异构体的蒽酮。熔点:223~224℃
  • F:10
  • Sigma Aldrich:481-72-1(sigmaaldrich)
  • 理化性质: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。从甲苯或乙醇中析出者为橙黄色针状结晶。相对分子质量270.25。熔点223~224℃。在二氧化碳气流中能升华。易溶于热乙醇、乙醚、苯,溶液呈黄色,也溶于氨水溶液及硫酸中,溶液呈绯红色。 芦荟的主要有效成分是芦荟苷和芦荟大黄素,芦荟汁有消炎、抗炎和促进损伤皮肤愈合的作用。 以上信息由Chemicalbook彤彤编辑整理。
  • 用途一:具有抗菌作用,对葡萄球菌、链球菌、白喉、枯草、痢疾等杆菌均有抑制作用。还有泻下作用,临床用作泻药。

系列性分类


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