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MedKoo Cat#: 525871 | Name: Bergapten
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bergapten is an anti-convulsant, showing activity against T. muris.

Chemical Structure

Bergapten
CAS#484-20-8

Theoretical Analysis

MedKoo Cat#: 525871

Name: Bergapten

CAS#: 484-20-8

Chemical Formula: C12H8O4

Exact Mass: 216.0423

Molecular Weight: 216.19

Elemental Analysis: C, 66.67; H, 3.73; O, 29.60

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 750.00 2 Weeks
10g USD 1,050.00 2 Weeks
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Related CAS #
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Synonym
Bergapten; 5-Methoxypsoralen; Geralen; Heraclin; Majudin
IUPAC/Chemical Name
4-Methoxyfuro[3,2-g]chromen-7-one
InChi Key
BGEBZHIAGXMEMV-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
SMILES Code
O=C1C=CC2=C(OC)C3=C(OC=C3)C=C2O1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Bergapten is an anti-convulsant.
In vitro activity:
Bergapten (BG) inhibited LPS-stimulated productions of TNF-α, IL-1β, IL-6, PGE2 and NO as well as the expression of iNOS and COX-2, and at the same time, it increased LPS-induced release of IL-10 in a dose-dependent manner in RAW264.7 cells. Mechanistically, BG suppressed the activations of JAK/STAT, but not that of MAPKs and NF-κB. In addition, BG, as an antioxidant, prevented the accumulation of ROS, which further exerted its anti-inflammatory function. Reference: Int Immunopharmacol. 2017 Jul;48:159-168. https://www.sciencedirect.com/science/article/pii/S1567576917301601?via%3Dihub
In vivo activity:
In vivo, Bergapten reduced endotoxin lethality in mice. Reference: Int Immunopharmacol. 2017 Jul;48:159-168. https://www.sciencedirect.com/science/article/pii/S1567576917301601?via%3Dihub
Solvent mg/mL mM comments
Solubility
DMSO 15.0 69.38
DMF 30.0 138.77
DMF:PBS (pH 7.2) (1:1) 0.5 2.31
Ethanol 1.0 4.63
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 216.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Zhou Y, Wang J, Yang W, Qi X, Lan L, Luo L, Yin Z. Bergapten prevents lipopolysaccharide-induced inflammation in RAW264.7 cells through suppressing JAK/STAT activation and ROS production and increases the survival rate of mice after LPS challenge. Int Immunopharmacol. 2017 Jul;48:159-168. doi: 10.1016/j.intimp.2017.04.026. Epub 2017 May 14. PMID: 28511114.
In vitro protocol:
1. Zhou Y, Wang J, Yang W, Qi X, Lan L, Luo L, Yin Z. Bergapten prevents lipopolysaccharide-induced inflammation in RAW264.7 cells through suppressing JAK/STAT activation and ROS production and increases the survival rate of mice after LPS challenge. Int Immunopharmacol. 2017 Jul;48:159-168. doi: 10.1016/j.intimp.2017.04.026. Epub 2017 May 14. PMID: 28511114.
In vivo protocol:
1. Zhou Y, Wang J, Yang W, Qi X, Lan L, Luo L, Yin Z. Bergapten prevents lipopolysaccharide-induced inflammation in RAW264.7 cells through suppressing JAK/STAT activation and ROS production and increases the survival rate of mice after LPS challenge. Int Immunopharmacol. 2017 Jul;48:159-168. doi: 10.1016/j.intimp.2017.04.026. Epub 2017 May 14. PMID: 28511114.
1: Zhang HL, Wu XY, Mi J, Peng YJ, Wang ZG, Liu Y, Wu XL, Gao Y. A new anti-inflammatory alkaloid from roots of Heracleum dissectum. Chem Biodivers. 2017 May 27. doi: 10.1002/cbdv.201700184. [Epub ahead of print] PubMed PMID: 28556437. 2: Zhou Y, Wang J, Yang W, Qi X, Lan L, Luo L, Yin Z. Bergapten prevents lipopolysaccharide-induced inflammation in RAW264.7 cells through suppressing JAK/STAT activation and ROS production and increases the survival rate of mice after LPS challenge. Int Immunopharmacol. 2017 May 13;48:159-168. doi: 10.1016/j.intimp.2017.04.026. [Epub ahead of print] PubMed PMID: 28511114. 3: Rajtar B, Skalicka-Woźniak K, Świątek Ł, Stec A, Boguszewska A, Polz-Dacewicz M. Antiviral effect of compounds derived from Angelica archangelica L. on Herpes simplex virus-1 and Coxsackievirus B3 infections. Food Chem Toxicol. 2017 May 6. pii: S0278-6915(17)30239-9. doi: 10.1016/j.fct.2017.05.011. [Epub ahead of print] PubMed PMID: 28487231. 4: Zheng Y, Xu X, Yuan F, Yao M, Ji S, Huang Z, Zhang F. Simultaneous Analysis of Simple Coumarins and Furocoumarines in Cigarettes by Solid-Phase Extraction with Gas Chromatography-Mass Spectrometry. J AOAC Int. 2017 Apr 20. doi: 10.5740/jaoacint.16-0192. [Epub ahead of print] PubMed PMID: 28425389. 5: Azietaku JT, Ma H, Yu XA, Li J, Oppong MB, Cao J, An M, Chang YX. A review of the ethnopharmacology, phytochemistry and pharmacology of Notopterygium incisum. J Ethnopharmacol. 2017 Apr 18;202:241-255. doi: 10.1016/j.jep.2017.03.022. Epub 2017 Mar 21. Review. PubMed PMID: 28336469. 6: Melough MM, Vance TM, Lee SG, Provatas AA, Perkins C, Qureshi A, Cho E, Chun OK. Furocoumarin Kinetics in Plasma and Urine of Healthy Adults Following Consumption of Grapefruit (Citrus paradisi Macf.) and Grapefruit Juice. J Agric Food Chem. 2017 Mar 29. doi: 10.1021/acs.jafc.7b00317. [Epub ahead of print] PubMed PMID: 28322044. 7: Wrześniok D, Beberok A, Rok J, Delijewski M, Hechmann A, Oprzondek M, Rzepka Z, Bacler-Żbikowska B, Buszman E. UVA radiation augments cytotoxic activity of psoralens in melanoma cells. Int J Radiat Biol. 2017 Mar 13:1-6. doi: 10.1080/09553002.2017.1297903. [Epub ahead of print] PubMed PMID: 28287037. 8: Teye Azietaku J, Yu XA, Li J, Hao J, Cao J, An M, Tan Z, Chang YX. Simultaneous Determination of Bergapten, Imperatorin, Notopterol, and Isoimperatorin in Rat Plasma by High Performance Liquid Chromatography with Fluorescence Detection and Its Application to Pharmacokinetic and Excretion Study after Oral Administration of Notopterygium incisum Extract. Int J Anal Chem. 2016;2016:9507246. doi: 10.1155/2016/9507246. Epub 2016 Dec 26. PubMed PMID: 28115935; PubMed Central PMCID: PMC5220503. 9: Madeiro SA, Borges NH, Souto AL, de Figueiredo PT, Siqueira-Junior JP, Tavares JF. Modulation of the antibiotic activity against multidrug resistant strains of coumarins isolated from Rutaceae species. Microb Pathog. 2017 Mar;104:151-154. doi: 10.1016/j.micpath.2017.01.028. Epub 2017 Jan 19. PubMed PMID: 28109770. 10: Deng X, Pu Q, Wang E, Yu C. Celery extract inhibits mouse CYP2A5 and human CYP2A6 activities via different mechanisms. Oncol Lett. 2016 Dec;12(6):5309-5314. doi: 10.3892/ol.2016.5317. Epub 2016 Oct 25. PubMed PMID: 28101244; PubMed Central PMCID: PMC5228217. 11: Eskandari EG, Doudi M, Abedi S. An in vitro study of antileishmanial effect of Portulaca oleracea extract. J Vector Borne Dis. 2016 Oct-Dec;53(4):362-369. PubMed PMID: 28035114. 12: Ma Y, Zhang Y, Zhai Y, Zhu Z, Pan Y, Qian D, Su S, Fan X, Duan J. Development of a UPLC-TQ/MS Approach for the Determination of Eleven Bioactive Components in Haizao Yuhu Decoction Plus-Minus Haizao and Gancao Drug Combination after Oral Administration in a Rat Model of Hypothyroidism. Molecules. 2016 Dec 22;22(1). pii: E7. doi: 10.3390/molecules22010007. PubMed PMID: 28025523. 13: Li XJ, Zhu Z, Han SL, Zhang ZL. Bergapten exerts inhibitory effects on diabetes-related osteoporosis via the regulation of the PI3K/AKT, JNK/MAPK and NF-κB signaling pathways in osteoprotegerin knockout mice. Int J Mol Med. 2016 Dec;38(6):1661-1672. doi: 10.3892/ijmm.2016.2794. Epub 2016 Nov 2. PubMed PMID: 27840967; PubMed Central PMCID: PMC5117769. 14: George S, Venkataraman R, Baby S. Melicodenine I, a new quinolinone alkaloid from Melicope denhamii leaves. Nat Prod Res. 2017 Apr;31(8):890-895. doi: 10.1080/14786419.2016.1253075. Epub 2016 Nov 6. PubMed PMID: 27817202. 15: Yu XA, Azietaku JT, Li J, An M, He J, Hao J, Cao J, Chang YX. The pharmacokinetics, bioavailability and excretion of bergapten after oral and intravenous administration in rats using high performance liquid chromatography with fluorescence detection. Chem Cent J. 2016 Oct 14;10:62. eCollection 2016. PubMed PMID: 27795734; PubMed Central PMCID: PMC5064970. 16: Wang C, Huo X, Tian X, Xu M, Dong P, Luan Z, Wang X, Zhang B, Zhang B, Huang S, Deng S, Ma X. Inhibition of melatonin metabolism in humans induced by chemical components from herbs and effective prediction of this risk using a computational model. Br J Pharmacol. 2016 Nov;173(22):3261-3275. doi: 10.1111/bph.13612. Epub 2016 Oct 10. PubMed PMID: 27588415; PubMed Central PMCID: PMC5071560. 17: Richardson JS, Sethi G, Lee GS, Malek SN. Chalepin: isolated from Ruta angustifolia L. Pers induces mitochondrial mediated apoptosis in lung carcinoma cells. BMC Complement Altern Med. 2016 Oct 12;16(1):389. PubMed PMID: 27729078; PubMed Central PMCID: PMC5059921. 18: Fang K, Dong H, Jiang S, Li F, Wang D, Yang D, Gong J, Huang W, Lu F. Diosgenin and 5-Methoxypsoralen Ameliorate Insulin Resistance through ER-α/PI3K/Akt-Signaling Pathways in HepG2 Cells. Evid Based Complement Alternat Med. 2016;2016:7493694. doi: 10.1155/2016/7493694. Epub 2016 Aug 31. PubMed PMID: 27656241; PubMed Central PMCID: PMC5021865. 19: Bagchi VA, Siegel JP, Demkovich MR, Zehr LN, Berenbaum MR. Impact of Pesticide Resistance on Toxicity and Tolerance of Hostplant Phytochemicals in Amyelois Transitella (Lepidoptera: Pyralidae). J Insect Sci. 2016 Sep 12;16(1). pii: iew063. doi: 10.1093/jisesa/iew063. Print 2016. PubMed PMID: 27620560; PubMed Central PMCID: PMC5019020. 20: Wangchuk P, Giacomin PR, Pearson MS, Smout MJ, Loukas A. Identification of lead chemotherapeutic agents from medicinal plants against blood flukes and whipworms. Sci Rep. 2016 Aug 30;6:32101. doi: 10.1038/srep32101. PubMed PMID: 27572696; PubMed Central PMCID: PMC5004179.