Apigenin 芹菜素

CAS 520-36-5 MFCD00006831

化学结构图

520-36-5
SMILES: O=c1cc(-c2ccc(O)cc2)oc2cc(O)cc(O)c12

化学属性

Mol. FormulaC15H10O5
Mol. Weight270
Melting Point>300
TSCANo
Density1.548
Stability对光敏感
Appearance 黄色针状结晶(吡啶水溶液),熔点345-350℃。几乎不溶于水,尚易溶于热乙醇。UVλEtOH max nm(ε):269(18800); 300(13500), 340(20900)。 powder
SolubilityDMSO: 27 mg/mL

别名和识别编码

Chemical NameApigenin
CAS Number520-36-5
Synonym 芹菜苷元 APIGENIN CRYSTALLINE 4,5,7-TRIHYDROXYFLAVONE 4',5,7-Trihydroxyflavone 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone 4',5,7-TRIHYDROXYFLAVONE APIGENIN FROM PARSLEY 4',5,7-Trihydroxyflavone Matricaria chamomilla flower 芹菜苷配基 agigenin 5,7,4'-三羟基黄酮 apigenol 4,5,7-Trihydroxyflavone (apigenin) 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one Chamomile 5,7,4'-TRIHYDROXYFLAVONE 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)- 2-(p-hydroxyphenyl)-5,7-dihydroxychromone 芹黄素,4',5,7-三羟基黄酮,5,7,4'-三羟基黄酮 4,5,7-Trihydroxyflavone 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone
MDL NumberMFCD00006831
Beilstein Registry Number262620
EC Number208-292-3
Reaxys-RN262620
PubChem Substance ID5280443
Merck Number730
Chemical Name Translation芹菜素
Wiswesser Line NotationT66 BO EVJ CR DQ& GQ IQ
LabNetwork Molecule IDLN00215854
InChIInChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
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分类

  • {SNA} AN-AZ, Allium sativum (Garlic), Anti-Proliferative Agents, Antitumor Agents, Apoptosis and Cell Cycle, Biochemicals and Reagents, Cell Cycle Proteins, Antibodies and Reagents, Cell Cycle Regulators, Chamaemelum nobile (Chamomile tea), Chemopreventive Agents, Cichorium intybus (Chicory), Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, Ephedra sinica, Fatty Acid Metabolism in Oncogenesis, Fatty Acid Synthase (FAS) Inhibitors, Flavonoids, Flavonols, and Flavanols, Ginkgo biloba, Inhibitors and Activators of Fatty Acid Metabolism, L to O, Linum usitatissimum (Flax), MAP Kin
  • {SNA} Biochemicals and

产品应用

  • 黄酮类化合物(flavonoid),能捕获细胞周期的G2/M期,抑制细胞扩增。抑制生长,诱发凋亡,用于肿瘤药物。

相关文献及参考

  • [2]. Wu K, et al. Inhibitory effects of apigenin on the growth of gastric carcinoma SGC-7901 cells. World J Gastroenterol. 2005 Aug 7;11(29):4461-4.
  • [3]. Yu W, et al. Apigenin Attenuates Adriamycin-Induced Cardiomyocyte Apoptosis via the PI3K/AKT/mTOR Pathway. Evid Based Complement Alternat Med. 2017;2017:2590676.
  • Chaumontet, C., et al.: Carcinogenesis, 15, 2325 (1994),
  • Czyz, J., et al., Hierarchy of carcinoma cell responses to apigenin: gap junctional coupling versus proliferation. Oncol. Rep. 11 , 739-744, (2004)
  • Huang, Y.T., et al., Inhibition of protein kinase C and proto-oncogene expression in NIH 3T3 cells by apigenin. Eur. J. Cancer 32A , 146-151, (1996) 摘要
  • Merck: 14,730
  • Merck: 14,730 Beilstein:18(5)4,574
  • Plaumann, B., et al., Flavonoids activate wild-type p53. Oncogene 13 , 1605-1614, (1996) 摘要
  • Sato, F., et al., Apigenin induces morphological differentiation and G2-M arrest in rat neuronal cells. Biochem

安全信息

GHS Symbol
RTECSLK9276000
Precautionary statements
  • 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。
  • 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
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P332+P313
  • P305+P351+P338+P337+P313
  • P302+P350
  • P337+P313
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
Safety Statements
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • 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 Wear suitable gloves 戴适当手套;
  • 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;
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
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xi
Storage condition -20°C 避光,储存温度-20°C
TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 100 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

TYPE OF TEST            : Micronucleus test
TEST SYSTEM             : Human Lymphocyte
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: 246,205,1991

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
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: 246,205,1991

其他信息

  • 刺激数据:有轻微过敏性
  • 类别:有毒物质
  • 灭火剂:水,二氧化碳, 泡沫, 干粉
  • 植物来源:芹菜素(Apigenin)是天然存在的一种黄酮类化合物,以植物黄色素的形式存在于多种植物中,主要来源于伞形科植物旱芹,其他植物如洋甘菊、蜜蜂花、紫苏、马鞭草、西洋蓍草中也发现有它的存在。 洋甘菊原产于英国,栽种于德国、法国和摩洛哥。罗马洋甘菊和德国洋甘菊有许多共同的特征:约30公分高,中心黄色,花办白色,略为毛茸茸的叶片。洋甘菊都有帮助睡眠的功效,缓解病人的发炎和疼痛症状,缓解由神经性皮肤瘙痒引起的失眠。中国也有大量栽培,用以入药和制茶。日常销售凉茶的成分之中都含有芹菜素,主要来自母菊洋甘菊干花。 以上信息由Chemicalbook的晓楠编辑整理。
  • 储运特性:库房低温通风干燥
  • color:yellow
  • 可燃性危险特性:热分解辛辣刺激烟雾
  • 图谱信息:芹菜素(520-36-5)红外图谱(IR1) 芹菜素(520-36-5)质谱(MS) 芹菜素(520-36-5)红外图谱(IR2)
  • 用途一:黄酮类化合物(flavonoid),能捕获细胞周期的G2/M期,抑制细胞扩增。抑制生长,诱发凋亡,用于肿瘤药物。
  • Alfa Aesar:4',5,7-三羟基黄酮,97% 4',5,7-Trihydroxyflavone, 97%(520-36-5)
  • 芹菜素价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 A1514 芹菜素 Apigenin 100MG 1360元 2010/05/25 L15041 4',5,7-三羟基黄酮,97% 4',5,7-Trihydroxyflavone, 97% 25mg 552元 2010/05/25 L15041 4',5,7-三羟基黄酮,97% 4',5,7-Trihydroxyflavone, 97% 100mg 1540元
  • MOL 文件:520-36-5.mol
  • TCI Shanghai:芹菜素 Apigenin,>;98.0%(LC)(520-36-5)
  • F:10
  • 芹菜素属于多酚类黄酮类化合物,以植物黄色素的形式存在于多种植物中,吡啶水溶液呈黄色针晶,无嗅无味。几乎不溶于水,部分溶于热酒精,溶于稀KOH溶液。
  • 生物活性和药理作用:芹菜素分子结构决定了其独特的生理学效应和生物学特性,具有很好的生物学作用,国内外大量研究发现,芹菜素是天然抗氧化剂,有降血压和舒张血管、预防动脉粥样硬化、抑制肿瘤等作用。与其他黄酮类物质(槲皮素、山奈黄酮)相比具有低毒、无诱变性等特点。目前,芹菜素在医药、食品等行业有一定的应用。但由于芹菜素的水溶性较差、肠道吸收少,导致其口服生物利用度较低、体内活性较低而在一定程度上限制了它的应用。
  • 理化性质:黄色针状结晶(吡啶水溶液),mp.345℃~350℃。几乎不溶于水,尚易溶于热乙醇,溶于稀氢氧化钾KOH溶液。芹菜素具有利尿、调节血压、 抗菌、消炎等方面的作用。

系列性分类


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