Determine the necessary mass, volume, or concentration for preparing a solution.
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Synonyms | naringenin | 480-41-1 | salipurpol | Salipurol | (S)-Naringenin | (S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one | Naringenine | pelargidanon | naringetol | (2S)-Naringenin | Asahina | NARIGENIN | NSC 11855 | CCRIS 5839 | (-)-(2S)-Naringenin | C15H12O5 | UNII-HN5425SBF2 | NSC 34875 | 5, |
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Specifications & Purity | 10mM in DMSO |
Storage Temp | Store at -80°C |
Shipped In | Ice chest + Ice pads |
Product Description | Naringenin is a flavonoid commonly found in grapefruits which functions as an antioxidant, free radical scavenger, anti-inflammatory compound, carbohydrate metabolism promoter, and immune system modulator. Studies indicate that in vitro Naringenin reduces oxidative damage to DNA. In addition, Naringenin potently inhibits the secretion of very-low-density lipoproteins by cells. Furthermore, Naringenin has been shown to reduce cholesterol concentrations in hepatocytes and plasma cells via inhibiting HMGCR (HMG-CoA reductase). Studies conducted on Hepatitis C virus particles demonstrate that Naringenin can inhibit the virus via a PPAR-mediated mechanism by inhibiting the long term assembly of the virus. |
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IUPAC Name | (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one |
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INCHI | InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1 |
InChi Key | FTVWIRXFELQLPI-ZDUSSCGKSA-N |
Canonical SMILES | C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O |
Isomeric SMILES | C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O |
PubChem CID | 439246 |
Molecular Weight | 272.25 |
Beilstein | 280888 |
Enter Lot Number to search for COA:
Boil Point(°C) | 577.5 °C |
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Melt Point(°C) | 247-250°C |
Pictogram(s) | GHS07 |
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Signal | Warning |
Hazard Statements | H315:Causes skin irritation H319:Causes serious eye irritation |
Precautionary Statements | P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P264:Wash hands [and …] thoroughly after handling. P362+P364:Take off contaminated clothing and wash it before reuse. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. |
1. Ziyuan Deng, Chengling Lai, Jun Zhang, Fan Sun, Danting Li, Peiying Hao, Xuping Shentu, Kun Pang, Xiaoping Yu. (2024) Effects of Secondary Metabolites of Rice on Brown Planthopper and Its Symbionts. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 25 (1): (386). [PMID:38203556] |
2. Chengyun He, Lu Bai, Daqun Liu, Benguo Liu. (2023) Interaction mechanism of okra (Abelmoschus esculentus L.) seed protein and flavonoids: Fluorescent and 3D-QSAR studies. Food Chemistry-X, 20 (17): (101023). [PMID:38144792] |
3. Shuai-Nan Zhang, Qi Liu, Xu-Zhao Li, Wu-De Yang, Ying Zhou. (2024) Liver protein and metabolite biolabels reveal hepatoprotective effects and active compounds of Eucommiae folium: Exploration of new application of herb based on multi-omics and bioinformatics. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 239 (19): (115870). [PMID:38008044] |
4. Yu Liu, Xinqi Qiu, Minhui Zhang, Yali Lin, Hui Lan, Xican Li, Quanzhou Wu, Jianfeng He. (2024) Boronate affinity-based surface molecularly imprinted polymer microspheres using polyethyleneimine/dopamine coating for efficient selective recognition and separation of Ginsenoside Rb1. REACTIVE & FUNCTIONAL POLYMERS, 194 (8): (105780). [PMID:11790298] |
5. Chenyu Su, Yiting Li, Shanshan Liu, Hui Feng, Jie Wang, Shuo Yan. (2023) Star polymer soil delivery nanoplatform for applying biological agents in the field to control plant rhizosphere diseases. JOURNAL OF CONTROLLED RELEASE, 364 (406). [PMID:37924956] |
6. Jiafeng Wang, Longhui Shao, Xiaoyu Wu, Chun Liu, Su Ni, Ting Dai, Hongwei Liu, Hongbin Zhao. (2023) Electrospun sandwich mesh structures loaded with naringenin and vitamin K2 polycaprolactone/gelatin nanofibers synergistically promote bone regeneration. Materials Today Bio, 23 (26): (100794). [PMID:37766894] |
7. Yufeng Chen, Guobin Xia, Chunfeng Wang, Huawei Wu, Xiaogang Xu, Genxiang Mao, Jiong Wu, Zhenlei Zhao. (2023) Impact of dietary plant flavonoids on 7,8-dihydroxyflavone transepithelial transport in human intestinal Caco-2 cells. Food Science & Nutrition, [PMID:37970375] |
8. Yuan Meng, Zihao Wei, Changhu Xue. (2023) Deciphering the interaction mechanism and binding mode between chickpea protein isolate and flavonoids based on experimental studies and molecular simulation. FOOD CHEMISTRY, 429 (136848). [PMID:37454615] |
9. Shaoyan Zhang, Jinfeng Ning, Qingqing Wang, Wei Wang. (2023) Fluorescence enhancement of flavonoids and its application in ingredient determination for some traditional Chinese medicines by CE-LIF. Analytical Methods, 15 (24): (2964-2970). [PMID:37309583] |
10. Lei He, Qian Hu, Liyang Wei, Xuliyang Ge, Ning Yu, Ying Chen. (2023) Unravelling dynamic changes in non-volatile and volatile metabolites of pulses during soaking: An integrated metabolomics approach. FOOD CHEMISTRY, 422 (136231). [PMID:37141754] |
11. Jie Yan, Shuaishuai Ji, Tian Chang, Zhenyan Yu, Jing Zhang, Man Hu, Xiu Cheng, Qiang Huo. (2023) Construction of bionic nanoparticles camouflaged with macrophage membranes for drug delivery in breast cancer. JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, 84 (104433). [PMID:] |
12. Qin Yuan, Meng Fuliang, Xu Chunyu, Hu Zhenguo, Zhang Yimiao, Jia Yufei, Li Songjun, Yuan Xinhua. (2023) Preparation and Performance of Novel Flavonoid Phenols-Based Biomass-Modified Phenol Formaldehyde Resins. Journal of Inorganic and Organometallic Polymers and Materials, 33 (7): (1817-1829). [PMID:] |
13. Yu Li, Bo He, Chao Zhang, Yanji He, Tianyang Xia, Chunyu Zeng. (2023) Naringenin Attenuates Isoprenaline-Induced Cardiac Hypertrophy by Suppressing Oxidative Stress through the AMPK/NOX2/MAPK Signaling Pathway. Nutrients, 15 (6): (1340). [PMID:36986070] |
14. Pan Lixia, Ye Hangyu, Pi Xionge, Liu Wei, Wang Zhao, Zhang Yinjun, Zheng Jianyong. (2023) Effects of several flavonoids on human gut microbiota and its metabolism by in vitro simulated fermentation. Frontiers in Microbiology, 14 [PMID:36819019] |
15. Chun Xiao Li, Fu Rong Wang, Bing Zhang, Ze Yuan Deng, Hong Yan Li. (2023) Stability and antioxidant activity of phenolic compounds during in vitro digestion. JOURNAL OF FOOD SCIENCE, 88 (2): (696-716). [PMID:36617678] |
16. Mang-Mang Li, Yi-Ting Chen, Jin-Cang Ruan, Wen-Jun Wang, Ji-Guang Chen, Qing-Feng Zhang. (2023) Structure-activity relationship of dietary flavonoids on pancreatic lipase. Current Research in Food Science, 6 (100424). [PMID:36618100] |
17. Hua Zhang, QianYu Zhao, JunQiang Qiu, ZhanHua Wang, Xin Yang. (2023) Synthesis of a magnetic micelle molecularly imprinted polymers to selective adsorption of rutin from Sophora japonica. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1214 (123492). [PMID:36495684] |
18. Xiaoyu Cai, Songxue Wang, Huali Wang, Suwen Liu, Guishan Liu, Huibin Chen, Ji Kang, Hao Wang. (2023) Naringenin inhibits lipid accumulation by activating the AMPK pathway in vivo and vitro. Food Science and Human Wellness, 12 (1174). [PMID:] |
19. Dan Yu, Fei Liu, Changdong Zou, Xiao Yang. (2023) Municipal green waste promotes iron release from steelmaking slag in water. RESOURCES CONSERVATION AND RECYCLING, 188 (106722). [PMID:] |
20. Chunru Wang, Junyao Li, Xiangsheng Han, Shuai Liu, Xintao Gao, Chuanlong Guo, Xiaochen Wu. (2022) Silk sericin stabilized proanthocyanidins for synergetic alleviation of ulcerative colitis. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 220 (1021). [PMID:36007701] |
21. Hongwei Jiang, Lei Zhou, Yuefang Sun, Kaibo Yu, Wenzhi Yu, Yuqing Tian, Junping Liu, Liqiang Zou, Wei Liu. (2022) Polyphenol oxidase inhibited by 4-hydroxycinnamic acid and naringenin: Multi-spectroscopic analyses and molecular docking simulation at different pH. FOOD CHEMISTRY, 396 (133662). [PMID:35839725] |
22. Ren Chuanhong, Guo Yan, Xie Linfeng, Zhao Zhikang, Xing Mengyun, Cao Yunlin, Liu Yilong, Lin Jing, Grierson Donald, Zhang Bo, Xu Changjie, Chen Kunsong, Li Xian. (2022) Identification of UDP-rhamnosyltransferases and UDP-galactosyltransferase involved in flavonol glycosylation in Morella rubra. Horticulture Research, 9 [PMID:36072838] |
23. Zhengqi Dong, Xiangtao Wang, Mingyue Wang, Rui Wang, Zheng Meng, Xiaotong Wang, Bo Yu, Meihua Han, Yifei Guo. (2022) Optimization of Naringenin Nanoparticles to Improve the Antitussive Effects on Post-Infectious Cough. MOLECULES, 27 (12): (3736). [PMID:35744861] |
24. Yu Wang, Zhi-jian Lin, Jing Huang, Meng-zhen Chu, Xue-li Ding, Wen-jing Li, Qiu-yue Mao, Bing Zhang. (2022) An integrated study of Shenling Baizhu San against hyperuricemia: Efficacy evaluation, core target identification and active component discovery. JOURNAL OF ETHNOPHARMACOLOGY, 295 (115450). [PMID:35688256] |
25. Yejun Zhong, Lei Yang, Taotao Dai, Ziyi Zhu, Hongyu Chen, Jianyong Wu, Er Sheng Gong. (2022) Flavonoids enhance gel strength of ovalbumin: Properties, structures, and interactions. FOOD CHEMISTRY, 387 (132892). [PMID:35405558] |
26. Yejun Zhong, Lei Yang, Ziyi Zhu, Hongyu Chen, Chengmei Liu, Taotao Dai, Er Sheng Gong. (2022) Protective effect of ovalbumin-flavonoid hydrogel on thrombolytic activity and stability of nattokinase. FOOD RESEARCH INTERNATIONAL, 156 (111188). [PMID:35651046] |
27. Jie Zhao, Lin Huang, Renjie Li, Zhuangwei Zhang, Jin Chen, Hongjin Tang. (2022) Insights from multi-spectroscopic analysis and molecular modeling to understand the structure–affinity relationship and the interaction mechanism of flavonoids with gliadin. Food & Function, 13 (9): (5061-5074). [PMID:35404372] |
28. Shisheng Jiang, Chaoming Huang, Shulin Wang, Biyun Huang, Dan Wu, Guodong Zheng, Yi Cai. (2022) Network Pharmacology-Based Strategy for Predicting Therapy Targets of Citri Reticulatae Pericarpium on Myocardial Hypertrophy. Biomed Research International, 2022 (4293265). [PMID:35281609] |
29. Zhengqi Dong, Rui Wang, Mingyue Wang, Zheng Meng, Xiaotong Wang, Meihua Han, Yifei Guo, Xiangtao Wang. (2022) Preparation of Naringenin Nanosuspension and Its Antitussive and Expectorant Effects. MOLECULES, 27 (3): (741). [PMID:35164006] |
30. Huijie Chen, Jianqing Chen, Xu Shi, Lu Li, Shiwen Xu. (2021) Naringenin protects swine testis cells from bisphenol A-induced apoptosis via Keap1/Nrf2 signaling pathway. BIOFACTORS, 48 (1): (190-203). [PMID:34914851] |
31. Yonggang Du, Ge Zhao, Gonghui Shi, Yiming Wang, Wei Li, Shitong Ren. (2022) Effect of crosslink structure on mechanical properties, thermal stability and flame retardancy of natural flavonoid based epoxy resins. EUROPEAN POLYMER JOURNAL, 162 (110898). [PMID:] |
32. Qing-Hui Wen, Rui Wang, Si-Qi Zhao, Bo-Ru Chen, Xin-An Zeng. (2021) Inhibition of Biofilm Formation of Foodborne Staphylococcus aureus by the Citrus Flavonoid Naringenin. Foods, 10 (11): (2614). [PMID:34828898] |
33. Lang-Hong Wang,Man-Sheng Wang,Xin-An Zeng,Xi-Ming Xu,Charles S Brennan. (2017-09-02) Membrane and genomic DNA dual-targeting of citrus flavonoid naringenin against Staphylococcus aureus.. Integrative biology : quantitative biosciences from nano to macro, 9 ((10)): (820-829). [PMID:28862705] |
34. Jiazeng Yang,Jincai Liang,Lei Shao,Lihong Liu,Ke Gao,Jun-Liang Zhang,Zhenjiao Sun,Wendong Xu,Pengcheng Lin,Rongmin Yu,Jiachen Zi. (2020-02-01) Green production of silybin and isosilybin by merging metabolic engineering approaches and enzymatic catalysis.. Metabolic engineering, 59 (44-52). [PMID:32004707] |
35. Na Li,Liyan Liu,Huiqing Luo,Huaqiao Wang,Depo Yang,Feng He. (2020-07-28) Flavanone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics for Mitochondria-Imaging and Zebrafish-Imaging.. Molecules (Basel, Switzerland), 25 ((14)): [PMID:32708080] |
36. Liu, et al.. (2020) Rapid Screening ?-Glucosidase Inhibitors from Natural Products by At-Line Nanofractionation with Parallel Mass Spectrometry and Bioactivity Assessment.. Journal of Chromatography A, 1635 (461740-461740). [PMID:33271429] |
37. Shujun Xu,Bingxin Wu,Biying Zhong,Luoqi Lin,Yining Ding,Xiao Jin,Zhiwei Huang,Miaoyang Lin,Huanlin Wu,Danping Xu. (2021-10-27) Naringenin alleviates myocardial ischemia/reperfusion injury by regulating the nuclear factor-erythroid factor 2-related factor 2 (Nrf2) /System xc-/ glutathione peroxidase 4 (GPX4) axis to inhibit ferroptosis.. Bioengineered, 12 ((2)): (10924-10934). [PMID:34699317] |
1. Ziyuan Deng, Chengling Lai, Jun Zhang, Fan Sun, Danting Li, Peiying Hao, Xuping Shentu, Kun Pang, Xiaoping Yu. (2024) Effects of Secondary Metabolites of Rice on Brown Planthopper and Its Symbionts. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 25 (1): (386). [PMID:38203556] |
2. Chengyun He, Lu Bai, Daqun Liu, Benguo Liu. (2023) Interaction mechanism of okra (Abelmoschus esculentus L.) seed protein and flavonoids: Fluorescent and 3D-QSAR studies. Food Chemistry-X, 20 (17): (101023). [PMID:38144792] |
3. Shuai-Nan Zhang, Qi Liu, Xu-Zhao Li, Wu-De Yang, Ying Zhou. (2024) Liver protein and metabolite biolabels reveal hepatoprotective effects and active compounds of Eucommiae folium: Exploration of new application of herb based on multi-omics and bioinformatics. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 239 (19): (115870). [PMID:38008044] |
4. Yu Liu, Xinqi Qiu, Minhui Zhang, Yali Lin, Hui Lan, Xican Li, Quanzhou Wu, Jianfeng He. (2024) Boronate affinity-based surface molecularly imprinted polymer microspheres using polyethyleneimine/dopamine coating for efficient selective recognition and separation of Ginsenoside Rb1. REACTIVE & FUNCTIONAL POLYMERS, 194 (8): (105780). [PMID:11790298] |
5. Chenyu Su, Yiting Li, Shanshan Liu, Hui Feng, Jie Wang, Shuo Yan. (2023) Star polymer soil delivery nanoplatform for applying biological agents in the field to control plant rhizosphere diseases. JOURNAL OF CONTROLLED RELEASE, 364 (406). [PMID:37924956] |
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