Chrysophanic acid 大黄酚

CAS 481-74-3 MFCD00001208

化学结构图

481-74-3
SMILES: Cc1cc(O)c2c(c1)C(=O)c1cccc(O)c1C2=O

化学属性

Mol. FormulaC15 H10 O4
Mol. Weight254.24
Melting Point192-196°C
SolubilitySoluble in DMSO, not in water
Density1.476
Appearance Solid powder
Boiling Point489.5°C at 760 mmHg

别名和识别编码

Chemical NameChrysophanic acid
CAS Number481-74-3
Synonym 1 1,8-Dihydroxy-3-methyl-9,10-anthracenedione 1,8-Dihydroxy-3-methyl-anthraquinone 1,8-Dihydroxy-3-methylanthraquinone 1,8-dihydroxy-3-methyl-1 1,8-dihydroxy-3-methyl-anthraquinon 1,8-二羟基-3-甲基-蒽醌 2-Methyl-4,5-dihydroxyanthraquinone 2-methyl-4,5-dihydroxyanthraquinone 3-METHYLCHRYSAZIN 3-Methyl-1,8-dihydroxyanthraquinone 3-Methylchrysazin 3-methyl-1,8-dihydroxyanthraquinone 4,5-Dihydroxy-2-methylanthraquinone 8-二羟基-3-甲基蒽醌 9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- Anthraquinone, 1,8-dihydroxy-3-methyl- C.I. 75400 CHRYSOPHANIC ACID Chrysophanic Acid {} {} {} {} {} {} {} {} {} {PubChem} chrysophanol {} {} {} {} {} {} {PubChem} chrysophanic acid, ion (1-) {} {} {} {} {} {} {} {PubChem} chrysophanic acid {} {} {}
MDL NumberMFCD00001208
PubChem Substance ID10208
Beilstein Registry Number1252300
EC Number207-572-2
Reaxys-RN1252300
Merck Number2258
Chemical Name Translation大黄酚
Wiswesser Line NotationL C666 BV IVJ DQ F1 NQ
LabNetwork Molecule IDLN01266862
InChIInChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
FormulaC15H10O4
IUPAC Name1,8-dihydroxy-3-methylanthracene-9,10-dione
InChIKey1,8-dihydroxy-3-methylanthracene-9,10-dione
Canonical SMILESO=C1C2=C(C=CC=C2O)C(C3=CC(C)=CC(O)=C13)=O
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分类

  • Aloe Vera, Bioactive Small Molecules, Building Blocks, C15 to C38, Carbonyl Compounds, Cell Biology, Chemical Synthesis, DIG-DY, Ketones, Nutrition Research, Organic Building Blocks, Phytochemicals by Plant (Food/Spice/Herb)
  • {SNA} Aloe Vera, Bioactive Small Molecules, Building Blocks, C15 to C38, Carbonyl Compounds, Chemical Synthesis, DIG-DY, Ketones, Nutrition Research, Organic Building Blocks, Phytochemicals by Plant (Food/Spice/Herb), 细胞生物学
  • {SNA} Aloe Vera, Building Blocks,

产品应用

  • Chrysophanic acid (Chrysophanol ) is a a natural anthraquinone, has anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid preferentially blocked proliferation in SNU-C5 cells but not in other cell lines (HT7, HT29, KM12C, SW480, HCT116 and SNU-C4) with low levels of EGFR expression. Chrysophanic acid treatment in SNU-C5 cells inhibited EGF-induced phosphorylation of EGFR and suppressed activation of downstream signaling molecules, such as AKT, extracellular signal-regulated kinase (ERK) and the mammalian target of rapamycin (mTOR)/ribosomal protein S6 kinase (p70S6K). Chrysophanic acid (80 and 120 µm) significantly blocked cell proliferation when combined with the mTOR inhibitor, rapamycin. These findings offer the first evidence of anticancer activity for chrysophanic acid via EGFR/mTOR mediated signaling transduction pathway.

相关文献及参考

  • Merck 14 ,2258
  • Short: III/35E
  • McDougall, G., et al.: Food Chem., 119, 758 (2009),
  • Short: EINECS
  • Merck: 14,2258 Beilstein: 8,IV,3277
  • Liang, X., et al.: J. Pharm. Biomed. Anal., 51, 565 (2010),
  • Lu, B., et al.: Phytochem. Anal., 20, 385 (2009),
  • Merck: 14,2258

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。
  • 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
Hazard Codes Xi
RTECSCB6725000
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Signal word Warning
Storage condition -20°C -20℃ 0-10 0-10°C 2-8°C Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). 储存温度2-8°C
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；
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
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 100 ug/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 40,203,1976

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 500 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: 5,1489,1977

其他信息

  • MOL 文件:481-74-3.mol
  • MSDS 信息:1,8-Dihydroxy-3-methylanthraquinone(481-74-3).msds
  • Sigma Aldrich:481-74-3(sigmaaldrich)
  • Acros Organics:大黄酚(大黄根酸) Chrysophanic acid, 98%(481-74-3)
  • 大黄酚价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30042880 大黄根酸;大黄酚; 驱虫豆酸; 3-甲基-1,8-二羟基蒽醌 0．1g 15.2元 2010/06/21 211950500 大黄酚 Chrysophanic acid 98% 50 MG 604元 2010/06/21 211950010 大黄酚 Chrysophanic acid 98% 1 GR 5397元
  • F:8-10

系列性分类

  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. A - D - Alphabetical
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Life Sciences Standards - Chromatography
  5. Natural Compounds - Life Sciences Standards
  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. Medical Research Areas
  2. GPCR & G Protein
  3. EGFR
  1. Medical Research Areas
  2. JAK/STAT
  3. ERK
  1. Medical Research Areas
  2. PI3K/AKT/mTOR
  3. S6 Kinase

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