isoimperatorin
isoimperatorin
CAS: 482-45-1
Molecular Formula: C16H14O4
isoimperatorin - Names and Identifiers
| Name | isoimperatorin |
| Synonyms | Isomperatorin Isoimperatorin ISOIMPERATORIN isoimperatorin ISOIMPERATORIN(P) 4-PRENYLOXYPSORALEN Isoimperatorin 482-45-1 4-(3-Methylbut-2-enoxy)furo[3,2-g]chromen-7-one 4-(3-Methyl-but-2-enyloxy-furo[3,2-g]chromen-7-one 4-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one 7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(3-methyl-2-butenyl)oxy]- 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3-methyl-2-butenyl)oxy)- 7H-Furo[3,2-g][1]benzopyran-7-one, 4-((3-methyl-2-butenyl)oxy)- 7H-furo[3,2-g][1]benzopyran-7-one, 4-[(3-methyl-2-buten-1-yl)oxy]- |
| CAS | 482-45-1 |
| EINECS | 801-715-8 |
| InChI | InChI=1/C16H14O4/c1-10(2)5-7-19-16-11-3-4-15(17)20-14(11)9-13-12(16)6-8-18-13/h3-6,8-9H,7H2,1-2H3 |
isoimperatorin - Physico-chemical Properties
| Molecular Formula | C16H14O4 |
| Molar Mass | 270.28 |
| Density | 1.242±0.06 g/cm3(Predicted) |
| Melting Point | 107-111°C |
| Boling Point | 448.3±45.0 °C(Predicted) |
| Flash Point | 224.9°C |
| Solubility | Soluble in acetone, ethyl acetate, chloroform, ethanol, insoluble in water |
| Vapor Presure | 3.13E-08mmHg at 25°C |
| Appearance | Light yellow bulk crystal (ethyl acetate), white flake crystal (anhydrous ethanol) |
| Color | White to Pale Yellow |
| BRN | 1291723 |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.606 |
| MDL | MFCD00272155 |
| Physical and Chemical Properties | Derived from the Raeusch stem and skin of the Flacourtiajangomas Lour. |
| In vitro study | During a screening program for new agrochemicals from Chinese medicinal herbs, the ethanol extract of Notopterygium incisum rhizomes is found to possess strong nematicidal activity against the two species of nematodes, Bursaphelenchus xylophilus and Meloidogyne incognita . Based on bioactivity-guided fractionation, the four constituents are isolated from the ethanol extract and identified as Columbianetin, Falcarindiol, Falcarinol, and Isoimperatorin. Isoimperatorin also has LC 50 values of 21.83 μg/mL against B. xylophilus . When using 15 min UV light treatment, falcarindiol, falcarinol, and isoimperatorin demonstrated almost five times more toxic to the southern root-knot nematodes than in dark treatment while columbianetin showed only two times more toxic. isoimperatorin has been demonstrated to possess insecticidal activity against several insects, such as the cabbage aphid ( Brevicoryne brassicae ). Isoimperatorin is identified in the active fraction of Angelica dahurica (AD) extract. Isoimperatorin is usually used as the internal standard (IS). |
isoimperatorin - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | LV1513000 |
| HS Code | 29329990 |
isoimperatorin - Reference
| Reference Show more | 1. Cao Shuli Zhao Chunjie Cai Li Xia Jing Minqi Li Yibai. Simultaneous determination of psoralen, isopsoralen, atractylenolide Ⅲ and isoimperatorin in Shenling Baizhu powder by UPLC [J]. Journal of Shenyang Pharmaceutical University 2018 35(07):568-573. 2. Xiaofen Liu, Bing Lai, Bing song, Xiubi et al. Determination of three coumarins in radix glehniae from Fujian province by HPLC [J]. Modern distance education of traditional Chinese medicine in China, 18 Vol. 10, 2020. 3. Ke Lulin, Feng Xian, Huang Pinfang, et al. Simultaneous determination of imperatorin and isoimperatorin in human plasma by LC-MS/MS [J]. Journal of Clinical laboratory testing, 2019, 037(012):885-888. 4. Li Guijie, Liang Guolu, Cheng Yujiao, etc. Effect of pH value on hydration of epoxidized bergamot in citrus juice by on-line reaction-high performance liquid chromatography [J]. Food and Fermentation Industry, 2020, 046(003):242-249. 5. Zhang Wei, Zhu Zhijia, Zhang Jie, etc. Determination of three coumarins in angelica dahurica by liquid chromatography-tandem mass spectrometry [J]. Analytical Laboratory, 2012(05):104-108. 6. Cong Jianmin, Chen Fengqing, Ye Junshuang, etc. Study on extraction technology and antibacterial activity of coumarin from Melilotus [J]. Natural product research and development, 2014, 026(004):588-593,596. 7. Liu, Ling, Zhi, Xu, ran, Guo, Jin, et al. Simultaneous determination of six components in Fangzhi nasopharyngeal granules by HPLC-MS method [J]. Journal of Pharmaceutical Analysis 2014(5):830-835. 8. Zhu Chunlu, Wang Jing, Qiao Yuhang, et al. Determination of total coumarins and four coumarins in stewed Angelica dahurica [J]. Chinese national folk medicine, 2019(19). 9. Liu lingjiao, Zhi Xuran, Wu zonyao, etc. Determination of seven active components in Fangzhi nasopharyngeal granules by HPLC [J]. Chinese Pharmaceutical Journal, 2014, 49(017):1554-1558. 10. Zhang Ye, Sun Yanxue, Ma Yuheng, etc. Study on HPLC fingerprint of angelica dahurica [J]. Food and Drug, 2020, 022(002):130-134. 11. Zhu Chunlu, Wang Jing, Qiao Yuhang, et al. Study on serum pharmacochemistry of duliangwan [J]. Chinese Journal of Modern Applied Pharmacy, 37(4). 12. Xuelian Wang, Minmin Li, Junhua Hu, et al. Inhibitory effects of 18 coumarins on Colletotrichum gloeosporioides in Citrus [J]. Fruit trees in south China, 2013, 42(004):73-74. 13. Rao-Zhi, Chen Guangyu, He Qun, Yan Hao-yu, Xie Meng-Zhou. Study on processing technology of notopterygii Rhizoma [J]. Asia-Pacific traditional medicine, 2021,17(02):31-36. 14. Fu, Yao, et al. "Mechanism-based inactivation of cytochrome P450 2D6 by Notopterol." Chemico-biological interactions 322 (2020): 109053.https://doi.org/10.1016/j.cbi.2020.109053 15. Lu, Dan, et al. "Mechanism-based inactivation of cytochrome P450 2B6 by isopsoralen." Xenobiotica 46.4 (2016): 335-341.https:// doi.org/10.3109/00498254.2015.1077403 16. Cao, Jiaojiao, et al. "Mechanism-based inactivation of cytochrome P450 2B6 by isoimperatorin." Chemico-biological interactions 226 (2015): 23-29.https://doi.org/10.1016/j.cbi.2014.12.009 17. Yang, P, Gao, R, Liu, Z, et al. Analysis of chemical constituents and six compounds in Qu-feng-sheng-shi Granules via HPLC-ESI-Q/TOF-MSn and HPLC-UV technique. Biomedical Chromatography. 2020; 34:e4829. https://doi.org/10.1002/bmc.4829 18. Yang, Yan-Fang, Lei Zhang and Xiu-Wei Yang. "Distribution assessments of coumarins from Angelicae Pubescentis Radix in rat cerebrospinal fluid and brain by Liquid Chromatography Tandem Mass Spectrometry analysis." Molecules 23.1 (2018): 225.https://doi.or 19. [IF=5.192] Jiaojiao Cao et al."Mechanism-based inactivation of cytochrome P450 2B6 by isoimperatorin."Chem-Biol Interact. 2015 Jan;226:23 20. [IF=4.411] Liang Yang et al."New Insights into the Antibacterial Activity of Hydroxycoumarins against Ralstonia solanacearum."Molecules. 2016 Apr;21(4):468 21. [IF=5.34] Xiaohui Zhang et al."Discovery of tetrahydropalmatine and protopine regulate the expression of dopamine receptor D2 to alleviate migraine from Yuanhu Zhitong formula."Phytomedicine. 2021 Oct;91:153702 22. [IF=4.162] Guijie Li et al."Characterization of Oxygenated Heterocyclic Compounds and in vitro Antioxidant Activity of Pomelo Essential Oil."Drug Des Dev Ther. 2021; 15: 937-947 23. [IF=2.193] Yang Lan et al."Simultaneous Determination of Three Coumarins in Angelica dahurica 1H-qNMR Method: A Fast and Validated Method for Crude Drug Quality Control."J Anal Methods Chem. 2020;2020:8987560 24. [IF=1.902] Pengshuo Yang et al."Analysis of chemical constituents and six compounds in Qu-feng-sheng-shi Granules via HPLC-ESI-Q/TOF-MSn and HPLC-UV technique."Biomed Chromatogr. 2020 Jul;34(7):e4829 |
isoimperatorin - Reference Information
| pharmacological action | molecular formula C16H14O4, molecular weight 270.27, colorless needle crystal (ethanol), melting point 110~111 ℃. Isoimperatorin has antihypertensive, antispasmodic, anti-cancer effects, and can also treat psoriasis. |
| determination of isoimperatorin in noopterygium root | [chromatographic conditions] chromatographic column: μ bondapak C18 column (150mm × 6mm, 5 μm); Mobile phase: methanol-acetonitrile -0.25mol/L phosphoric acid solution (9:5:10); flow rate: 1.0 ml/min; Detection wavelength: 322nm; Column temperature: room temperature. [preparation of test samples] take about 50g of coarse powder of this product, refluxing and extracting with 8 times of 90% ethanol for 3 times, 1.5h each time, combine the extracts, recover ethanol, obtain 13.70g of extract, mix it with a proper amount of treated macroporous adsorption resin, place it on the treated macroporous adsorption resin column, and use water in turn, 20%, 30%, 40%, 50%, 60%, 70%, 80% and 90% are washed with ethanol until the eluent is colorless and evaporated in water bath to obtain paste, which is dissolved with 50% ethanol and fixed to 50ml. Determination according to the chromatographic conditions of this method. |
| biological activity | Isoimperatorin is a methanol extract of Angelica dahurica root, effectively inhibiting acetylcholinesterase (AChE),IC50 is 74.6 μM. |
| target | TargetValue AChE (Cell-free say) 74.6 μM |
| Target | Value |
| AChE (Cell-free assay) | <74.6 μM |
| in vitro study | During a screening program for new agrochemicals from Chinese medicinal herbs, the ethanol extract of Notopterygium incisum rhizomes is found to possess strong nematicidal activity against the two species of nematodes, bursaphelenchus xylophilus and Meloidogyne incognita . Based on bioactivity-guided fractionation, the four constituents are isolated from the ethanol extract and identified as Columbianetin, Falcarindiol, Falcarinol, and Isoimperatorin. Isoimperatorin also has LC 50 values of 21.83 μg/mL against B. xylophilus . When using 15 min UV light treatment, falcarindiol, falcarinol, and isoimperatorin demonstrated almost five times more toxic to the southern root-not nematodes than in dark treatment while columbianetin showedonly two times more toxic. isoimperatorin has been demonstrated to possess insecticidal activity against several insects, such as the cabbage aphid ( Brevicoryne brassicae ). Isoimperatorin is identified in the active fraction of Angelica dahurica (AD) extract. Isoimperatorin is usually used as the internal standard (IS). |
| chemical properties | derived from the Raeusch stem of the Flacourtiajangomas of Lour, skin |
| use | used for content determination/identification/pharmacological experiments, etc. |
| NIST chemical information | The information is: webbook.nist.gov provides (external link) |
| toxic substance data | The information is: pubchem.ncbi.nlm.nih.gov Provide (external link) |
Last Update：2024-04-09 21:31:57
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View History
isoimperatorin
36588-45-1
1122-71-0
dementholized
分散红5B
o-Nitrocinnamic acid
C.I. Pigment Red 179
Tantalum Nitride , powder (TaN)
FERRIC III PHOSPHATE
bis(methoxy)methane
36588-45-1
1122-71-0
dementholized
分散红5B
o-Nitrocinnamic acid
C.I. Pigment Red 179
Tantalum Nitride , powder (TaN)
FERRIC III PHOSPHATE
bis(methoxy)methane