482-44-0
9-(3-methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one
CAS: 482-44-0
Molecular Formula: C16H14O4
482-44-0 - Names and Identifiers
| Name | 9-(3-methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one |
| Synonyms | imperatorin IMPERATORIN 8-isopentenyloxypsoralene 9-(3-methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one 9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one 2-g)(1)benzopyran-7-one,9-((3-methyl-2-butenyl)oxy)-7h-furo( 9-[(3-methyl-2-butenyl)oxy]-7h-furo[3,2-g][1]benzopyran-7-one 9-((3-methyl-2-butenyl)oxy)-7h-furo(3,2-g)(1)benzopyran-7-one 6-hydroxy-7-((3-methyl-2-butenyl)oxy)-5-benzofuranacrylicacidelta-lacto 6-hydroxy-7-(3-methyl-2-butenyloxy)-5-benzofuranacrylicacidomega-lactone 6-hydroxy-7-((3-methyl-2-butenyl)oxy)-5-benzofuranacrylicacidelta-lactone |
| CAS | 482-44-0 |
| EINECS | 207-581-1 |
| InChI | InChI=1/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3 |
| InChIKey | OLOOJGVNMBJLLR-UHFFFAOYSA-N |
482-44-0 - Physico-chemical Properties
| Molecular Formula | C16H14O4 |
| Molar Mass | 270.28 |
| Density | 1.1311 (rough estimate) |
| Melting Point | 98-100°C |
| Boling Point | 333.4°C (rough estimate) |
| Flash Point | 224.9°C |
| Solubility | DMSO : 50 mg/mL (184.99 mM; Need ultrasonic);H2O : < 0.1 mg/mL (insoluble) |
| Vapor Presure | 3.13E-08mmHg at 25°C |
| Appearance | White flake crystal |
| Color | off-white to light brown |
| Maximum wavelength(λmax) | ['301nm(MeOH)(lit.)'] |
| Merck | 14,4925 |
| Storage Condition | -20°C |
| Refractive Index | 1.4350 (estimate) |
| MDL | MFCD00016881 |
| Physical and Chemical Properties | It is from the stem of Raeusch in the family flaviaceae, |
| In vitro study | Imperatorin is a plant secondary metabolite belonging to the coumarins-specifically the furanocoumarins. Imperatorin enhances the GABA-induced chloride ion current (I GABA ) through the α 1 β 2 γ 2S receptors. Imperatorin potentiates I GABA at 100 μmol by 50.5±16.3 % and at 300 μmol by 109.8±37.7 %, respectively. Imperatorin, together with Phellopterin, found in the roots of A. dahurica, inhibit [ 3 H]diazepam binding to the benzodiazepine site of the rat brain GABA A receptor in vitro with an IC 50 of 12.3 μmol for Imperatorin and 400 nmol for Phellopterin. Imperatorin, in a concentration ranging from 3.5 to 14 mmol, significantly and irreversibly inhibits GABA-T in a time-dependent and concentration-dependent manner, by irreversibly binding with the active site of GABA-T.Imperatorin is a reversible acetylcholinesterase (AChE) inhibitor, and acts in dose-dependent manner. The AChE and BChE inhibitory activities of Imperatorin and a crude extract from the fruits of Angelica archangelica L. is tested by the spectrophotometric method at concentrations of 12.5, 25, 50, and 100 μg/mL. Imperatorin displays low inhibition towards AChE (13.75-46.11 %), whereas it has remarkable inhibitory effect against BChE (37.46-83.98 %). Imperatorin shows selectivity toward BChE rather than AChE, with an IC 50 for BChE of 31.4 μmol. Imperatorin, together with (+)-Byakangelicol, are found to be the most effective BACE-1 inhibitors, with IC 50 s of 91.8 and 104.9 μmol, respectively. Imperatorin (IC 50 =9.2 μmol) is also effective as an inhibitor of NO synthesis. Imperatorin is a weak agonist of TRPV1, a channel implicated in detecting several noxious stimuli, exhibiting EC 50 of 12.6±3.2 μM. |
| In vivo study | At doses of 10 and 20 mg/kg and 30 min after injection, Imperatorin shows an anxiolytic effect and improved different stages of memory and learning processes-both acquisition and consolidation. It is also shown that acute administration Imperatorin at doses of 10 and 20 mg/kg reduced the anxiogenic effect of nicotine (0.1 mg/kg, subcutaneous, s.c.). At 30 and 40 mg/kg, i.p. Imperatorin significantly potentiates the anticonvulsant activity of carbamazepine against maximal electroshock-induced seizures expressed by lowering the ED 50 from 10.8 to 6.8 mg/kg (by 34 %) and 6 mg/kg (by 42 %), respectively. Moreover, Imperatorin at 30 mg/kg and carbamazepine at 6.8 mg/kg shows increases the total brain concentration of carbamazepine from 1.260 to 2.328 μg/mL (by 85%), which may be caused by modifying the blood-barrier permeability or acting like an inhibitor of multi-drug resistance proteins. Imperatorin, a naturally occurring furanocoumarin, inactivates gamma-aminobutyric acid transaminase and inhibits acetylcholinesterase activity. Imperatorin administered acutely at the doses of 5 and 10 mg/kg prior to the injection of scopolamine (1 mg/kg) improves memory acquisition and consolidation impaired by scopolamine. Furthermore, repeatable (7 days, twice daily) administration of the highest dose of Imperatorin (10 mg/kg) significantly attenuates the effects of scopolamine on memory acquisition, whereas the doses of 5 and 10 mg/kg of this furanocoumarin are effective when memory consolidation is measured . |
482-44-0 - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | LV1575000 |
| HS Code | 29419090 |
482-44-0 - Reference
| Reference Show more | 1. 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. 2. Ma Haiping, Wang, man, Xu, Shang, et al. Determination of imperatorin in biyankang capsules by HPLC [J]. Asia-Pacific traditional medicine 2020 v.16;No.223(03):56-61. 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. Yang Lan, Li Yan, Feng Yanmei et al. Determination of five index components in radix angelicae dahuricae by one-Test multi-evaluation method [J]. Jiangsu Journal of Agricultural Sciences 2020(1):199-205. 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. Huang Jiajia, long Xiaoyan, Wang Rui, etc. Optimization of percolation extraction of coumarins from Angelica dahurica [J]. Chinese patent medicine, 2019. 7. 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. 8. 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. 9. 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). 10. 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. 11. Zhang Ye, Sun Yanxue, Ma Yuheng, etc. Study on HPLC fingerprint of angelica dahurica [J]. Food and Drug, 2020, 022(002):130-134. 12. Yang Shuang, He Yanqian, Yang Jie, etc. Study on improving the quality standard of cold soft capsules [J]. Shi Zhen, Chinese Traditional Medicine, 2013, 24(008): 530-632. 13. 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. 14. Zheng, Liwei, et al. "Imperatorin is a mechanism-based inactivator of CYP2B6." Drug Metabolism and Disposition 43.1 (2015): 82-88.https://doi.org/10.1124/dmd.114.060558 15. 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 16. [IF=4.411] Liang Yang et al."New Insights into the Antibacterial Activity of Hydroxycoumarins against Ralstonia solanacearum."Molecules. 2016 Apr;21(4):468 17. [IF=2.044] Tang Cheng et al."Ligand Fishing with Cellular Membrane-Coated Magnetic Beads: A New Method for the Screening of Potentially Active Compounds from Natural Products."Chromatographia. 2017 Oct;80(10):1517-1525 18. [IF=6.576] Li Guijie et al."Effects of Cold-Pressing and Hydrodistillation on the Active Non-volatile Components in Lemon Essential Oil and the Effects of the Resulting Oils on Aging-Related Oxidative Stress in Mice."Front Nutr. 2021 Jun;0:329 19. [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 20. [IF=2.193] Yang Lan et al."Simultaneous Determination of Three Coumarins in Angelica dahurica by 1H-qNMR Method: A Fast and Validated Method for Crude Drug Quality Control."J Anal Methods Chem. 2020;2020:8987560 21. [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 22. [IF=3.269] Haosheng Zhang et al."Imperatorin alleviated NLR family pyrin domain-containing 3 inflammasome cascade-induced synovial fibrosis and synovitis in rats with knee osteoarthritis."Bioengineered. 2021;12(2):12954-12964 |
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View History
482-44-0
340168-52-7
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340168-52-7
ai3-51002
N-(PHOSPHONOMETHYL)IMINODIACETIC ACID
614-22-2
Citrus aurantium dulcis
pigment red 12
7218-04-4
永固红 F3R
60589-06-2