Scoparone | CAS#120-08-1 | anti-tumor

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

MedKoo CAT#: 584389

CAS#: 120-08-1

Description: Scoparone is a natural compound isolated from Artemisia capillaris. Traditionally used in Chinese herbal medicine to treat neonatal jaundice, this compound has been found to elicit anti-tumor effects against DU145 prostate cancer cells in part through inhibition of STAT3 activity.

Chemical Structure

Scoparone

CAS# 120-08-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 584389
Name: Scoparone
CAS#: 120-08-1
Chemical Formula: C11H10O4
Exact Mass: 206.06
Molecular Weight: 206.200
Elemental Analysis: C, 64.08; H, 4.89; O, 31.04

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 180
25mg	USD 350
50mg	USD 630
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Scoparone; Escoparone

IUPAC/Chemical Name: 6,7-Dimethoxy-2-benzopyrone

InChi Key: GUAFOGOEJLSQBT-UHFFFAOYSA-N

InChi Code: InChI=1S/C11H10O4/c1-13-9-5-7-3-4-11(12)15-8(7)6-10(9)14-2/h3-6H,1-2H3

SMILES Code: O=C1C=CC2=CC(OC)=C(OC)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:

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Biological target:	Scoparone has anticoagulant, vasorelaxant antioxidant, anti-inflammatory activities.
In vitro activity:	Scoparone is a promising agent for non-small-cell-lung cancer (NSCLC) treatment. Scoparone induced apoptosis and ferroptosis in NSCLC cells. Scoparone activated the ROS/JNK/SP1/ACSL4 axis to trigger ferroptosis in NSCLC cells. Scoparone treatment led to FBW7-mediated ubiquitination and downregulation of Mcl-1. Scopaone also induced Bax activation in an ROS-dependent manner. Reference: Toxicol In Vitro. 2023 Sep;91:105627. https://pubmed.ncbi.nlm.nih.gov/37315743/
In vivo activity:	In a murine model of non-alcoholic fatty liver disease (NAFLD) into hepatocellular carcinoma (HCC), scopparone could ameliorate pathological alterations observed in HAFLD-HCC disease progression. Scoparone administration reverted upregulation of NF-kB p65 expression in NAFLD and NAFLD-HCC models. Scoparone reversed increased mRNA expression levels of NF-κB target genes, which were originally elevated in NAFLD-HCC. Scoparone counteracted MAPK/Akt signaling activation in the NAFLD-HCC model. Reference: Environ Toxicol. 2023 Jul 12. Preprint. https://pubmed.ncbi.nlm.nih.gov/37436232/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	25.0	121.24
	DMSO	50.0	242.49
	Ethanol	1.0	4.85

Preparing Stock Solutions

The following data is based on the product molecular weight 206.20 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.

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. Shen H, Wei Y, Yang Q, Cai Y, Zhu K, Chen X. Scoparone induces both apoptosis and ferroptosis via multiple mechanisms in non-small-cell lung cancer cells. Toxicol In Vitro. 2023 Sep;91:105627. doi: 10.1016/j.tiv.2023.105627. Epub 2023 Jun 12. PMID: 37315743. 2. Wu X, Li X, Li J, Zhao X, Cui Y, Eerdun C. Scoparone inhibits breast cancer cell viability through the NF‑κB signaling pathway. Exp Ther Med. 2023 May 17;26(1):328. doi: 10.3892/etm.2023.12027. PMID: 37346408; PMCID: PMC10280323. 3. Ye M, Liu C, Liu J, Lu F, Xue J, Li F, Tang Y. Scoparone inhibits the development of hepatocellular carcinoma by modulating the p38 MAPK/Akt/NF-κB signaling in nonalcoholic fatty liver disease mice. Environ Toxicol. 2023 Jul 12. doi: 10.1002/tox.23851. Epub ahead of print. PMID: 37436232. 4. Jiang Y, Xu J, Huang P, Yang L, Liu Y, Li Y, Wang J, Song H, Zheng P. Scoparone Improves Nonalcoholic Steatohepatitis Through Alleviating JNK/Sab Signaling Pathway-Mediated Mitochondrial Dysfunction. Front Pharmacol. 2022 May 3;13:863756. doi: 10.3389/fphar.2022.863756. PMID: 35592421; PMCID: PMC9110978.
In vitro protocol:	1. Shen H, Wei Y, Yang Q, Cai Y, Zhu K, Chen X. Scoparone induces both apoptosis and ferroptosis via multiple mechanisms in non-small-cell lung cancer cells. Toxicol In Vitro. 2023 Sep;91:105627. doi: 10.1016/j.tiv.2023.105627. Epub 2023 Jun 12. PMID: 37315743. 2. Wu X, Li X, Li J, Zhao X, Cui Y, Eerdun C. Scoparone inhibits breast cancer cell viability through the NF‑κB signaling pathway. Exp Ther Med. 2023 May 17;26(1):328. doi: 10.3892/etm.2023.12027. PMID: 37346408; PMCID: PMC10280323.
In vivo protocol:	1. Ye M, Liu C, Liu J, Lu F, Xue J, Li F, Tang Y. Scoparone inhibits the development of hepatocellular carcinoma by modulating the p38 MAPK/Akt/NF-κB signaling in nonalcoholic fatty liver disease mice. Environ Toxicol. 2023 Jul 12. doi: 10.1002/tox.23851. Epub ahead of print. PMID: 37436232. 2. Jiang Y, Xu J, Huang P, Yang L, Liu Y, Li Y, Wang J, Song H, Zheng P. Scoparone Improves Nonalcoholic Steatohepatitis Through Alleviating JNK/Sab Signaling Pathway-Mediated Mitochondrial Dysfunction. Front Pharmacol. 2022 May 3;13:863756. doi: 10.3389/fphar.2022.863756. PMID: 35592421; PMCID: PMC9110978.

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1: Lee SH, Jang HD. Scoparone attenuates RANKL-induced osteoclastic differentiation through controlling reactive oxygen species production and scavenging. Exp Cell Res. 2015 Feb 15;331(2):267-77. doi: 10.1016/j.yexcr.2014.12.018. Epub 2015 Jan 6. PubMed PMID: 25576385.

2: Niu N, Li B, Hu Y, Li X, Li J, Zhang H. Protective effects of scoparone against lipopolysaccharide-induced acute lung injury. Int Immunopharmacol. 2014 Nov;23(1):127-33. doi: 10.1016/j.intimp.2014.08.014. Epub 2014 Aug 22. PubMed PMID: 25151099.

3: Yang D, Yang J, Shi D, Deng R, Yan B. Scoparone potentiates transactivation of the bile salt export pump gene and this effect is enhanced by cytochrome P450 metabolism but abolished by a PKC inhibitor. Br J Pharmacol. 2011 Nov;164(5):1547-57. doi: 10.1111/j.1476-5381.2011.01522.x. PubMed PMID: 21649640; PubMed Central PMCID: PMC3221107.

4: Park S, Kim JK, Oh CJ, Choi SH, Jeon JH, Lee IK. Scoparone interferes with STAT3-induced proliferation of vascular smooth muscle cells. Exp Mol Med. 2015 Mar 6;47:e145. doi: 10.1038/emm.2014.113. PubMed PMID: 25744297; PubMed Central PMCID: PMC4351406.

5: Yin Q, Sun H, Zhang A, Wang X. Pharmacokinetics and tissue distribution study of scoparone in rats by ultraperformance liquid-chromatography with tandem high-definition mass spectrometry. Fitoterapia. 2012 Jun;83(4):795-800. doi: 10.1016/j.fitote.2012.03.010. Epub 2012 Mar 16. PubMed PMID: 22465507.

6: Son DJ, Lee GR, Oh S, Lee SE, Choi WS. Gastroprotective efficacy and safety evaluation of scoparone derivatives on experimentally induced gastric lesions in rodents. Nutrients. 2015 Mar 13;7(3):1945-64. doi: 10.3390/nu7031945. PubMed PMID: 25781220; PubMed Central PMCID: PMC4377892.

7: Kim JK, Kim JY, Kim HJ, Park KG, Harris RA, Cho WJ, Lee JT, Lee IK. Scoparone exerts anti-tumor activity against DU145 prostate cancer cells via inhibition of STAT3 activity. PLoS One. 2013 Nov 15;8(11):e80391. doi: 10.1371/journal.pone.0080391. eCollection 2013. PubMed PMID: 24260381; PubMed Central PMCID: PMC3829856.

8: Müller-Enoch D, Greischel A. Differentiation of cytochrome P-450 activities with scoparone as substrate. A rapid one-step HPLC-analysis. Arzneimittelforschung. 1988 Oct;38(10):1520-2. PubMed PMID: 3196394.

9: Müller-Enoch D, Büttgen E, Nonnenmacher A. Regioselective O-demethylation of scoparone: differentiation between rat liver cytochrome P-450 isozymes. Z Naturforsch C. 1985 Sep-Oct;40(9-10):682-4. PubMed PMID: 4082729.

10: Yang YJ, Lee HJ, Lee BK, Lim SC, Lee CK, Lee MK. Effects of scoparone on dopamine release in PC12 cells. Fitoterapia. 2010 Sep;81(6):497-502. doi: 10.1016/j.fitote.2010.01.003. Epub 2010 Jan 18. PubMed PMID: 20080157.

11: Liu YY, Yu H, Yuan F, Zhou F, Chen YG. [Study on distributed patterns of scoparone and ayapin in Dendrobium species from Yunnan]. Zhongguo Zhong Yao Za Zhi. 2013 Nov;38(21):3691-5. Chinese. PubMed PMID: 24494556.

12: Zhang A, Sun H, Wu G, Sun W, Yuan Y, Wang X. Proteomics analysis of hepatoprotective effects for scoparone using MALDI-TOF/TOF mass spectrometry with bioinformatics. OMICS. 2013 Apr;17(4):224-9. doi: 10.1089/omi.2012.0064. Epub 2013 Mar 20. PubMed PMID: 23514563; PubMed Central PMCID: PMC3615692.

13: Noh JR, Kim YH, Hwang JH, Gang GT, Yeo SH, Kim KS, Oh WK, Ly SY, Lee IK, Lee CH. Scoparone inhibits adipocyte differentiation through down-regulation of peroxisome proliferators-activated receptor γ in 3T3-L1 preadipocytes. Food Chem. 2013 Nov 15;141(2):723-30. doi: 10.1016/j.foodchem.2013.04.036. Epub 2013 Apr 19. PubMed PMID: 23790840.

14: Kang JW, Kim DW, Choi JS, Kim YS, Lee SM. Scoparone attenuates D-galactosamine/lipopolysaccharide-induced fulminant hepatic failure through inhibition of toll-like receptor 4 signaling in mice. Food Chem Toxicol. 2013 Jul;57:132-9. doi: 10.1016/j.fct.2013.03.016. Epub 2013 Mar 25. PubMed PMID: 23535186.

15: Zhang A, Qiu S, Sun H, Zhang T, Guan Y, Han Y, Yan G, Wang X. Scoparone affects lipid metabolism in primary hepatocytes using lipidomics. Sci Rep. 2016 Jun 16;6:28031. doi: 10.1038/srep28031. PubMed PMID: 27306123; PubMed Central PMCID: PMC4910084.

16: Yang JY, Koo JH, Song YG, Kwon KB, Lee JH, Sohn HS, Park BH, Jhee EC, Park JW. Stimulation of melanogenesis by scoparone in B16 melanoma cells. Acta Pharmacol Sin. 2006 Nov;27(11):1467-73. PubMed PMID: 17049123.

17: Horsmans Y, Desager JP, Harvengt C. Scoparone O-demethylase assay is not useful to differentiate the effects of model inducers of cytochrome P-450 in rabbit and guinea pig liver. Life Sci. 1993;53(25):PL421-6. PubMed PMID: 8255142.

18: Mennes WC, Luijckx NB, Wortelboer HM, Noordhoek J, Blaauboer BJ. Differences in the effects of model inducers of cytochrome P450 on the biotransformation of scoparone in rat and hamster liver. Arch Toxicol. 1993;67(2):92-7. PubMed PMID: 8481107.

19: Lv H, Sun H, Wang X, Sun W, Jiao G, Zhou D, Zhao L, Cao H, Zhang G. Simultaneous determination by UPLC-ESI-MS of scoparone, capillarisin, rhein, and emodin in rat urine after oral administration of Yin Chen Hao Tang preparation. J Sep Sci. 2008 Mar;31(4):659-66. doi: 10.1002/jssc.200700596. PubMed PMID: 18264991.

20: Huang HC, Huang YL, Chang JH, Chen CC, Lee YT. Possible mechanism of immunosuppressive effect of scoparone (6,7-dimethoxycoumarin). Eur J Pharmacol. 1992 Jul 7;217(2-3):143-8. PubMed PMID: 1425935.

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