Silymarin | CAS#65666-07-1 | antihepatoxic agent

MedKoo Cat#: 598544 | Name: Silymarin

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Description:

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

Silymarin displays antioxidant and membrane stabilizing activity. It protects various tissues and organs against chemical injury, and shows potential as an antihepatoxic agent.

Chemical Structure

Silymarin

CAS#65666-07-1

Theoretical Analysis

MedKoo Cat#: 598544

Name: Silymarin

CAS#: 65666-07-1

Chemical Formula: C25H22O10

Exact Mass: 482.1213

Molecular Weight: 482.44

Elemental Analysis: C, 62.24; H, 4.60; O, 33.16

Price and Availability

Size	Price	Availability	Quantity
10g	USD 295.00
50g	USD 750.00
500g	USD 4,250.00
1kg	USD 5,650.00

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Synonym

Silymarin; Milk thistle; Legalon 70; Flavobion; Wild Artichoke; Silybum marianum; Silybin; Silybine; Silimarin

IUPAC/Chemical Name

(2R,3R)-3,5,7-trihydroxy-2-((2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one

InChi Key

SEBFKMXJBCUCAI-WAABAYLZSA-N

InChi Code

InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23-,24-,25+/m0/s1

SMILES Code

COc1c(O)ccc([C@@H]2Oc3c(O[C@H]2CO)ccc([C@H]4Oc5c(C([C@@H]4O)=O)c(O)cc(O)c5)c3)c1

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

>3 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

2932996100

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Silymarin is an effective SARS-CoV-2 main protease (Mpro) inhibitor. Silymarin can significantly reduce tumor cell proliferation, angiogenesis as well as insulin resistance. Silymarin has the chemopreventive effect on hepatocellular carcinoma (HCC). Silymarin has the potential for COVID-19 research.

In vitro activity:

Silymarin has potential for development as a cancer therapeutic due to its growth inhibitory effects and induction of apoptosis in human gastric cancer cells. In AGS human gastric cancer cells, silymarin increased the expression of Bax, phosphorylated (p)‑JNK and p‑p38, and cleaved poly‑ADP ribose polymerase, and decreased the levels of Bcl‑2 and p‑ERK1/2 in a concentration‑dependent manner. Reference: Oncol Rep. 2019 Nov;42(5):1904-1914. https://pubmed.ncbi.nlm.nih.gov/31485597/

In vivo activity:

Silymarin may be an efficient and novel therapy for the prevention of peritoneal fibrosis (PF) through inhibition of TGF-β/Smad signaling. Silymarin alleviated peritoneal dysfunction and inhibited the expression of fibrotic markers (TGF-β1, collagen I, fibronectin) and restored the expression of E-cadherin, BMP-7 in PF mice Reference: Arch Pharmacol. 2023 Oct;396(10):2379-2391. https://pubmed.ncbi.nlm.nih.gov/37052642/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	41.16
	DMSO	10.0	20.73
	Ethanol	0.1	0.21

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 482.44 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. Sardanelli AM, Isgrò C, Palese LL. SARS-CoV-2 Main Protease Active Site Ligands in the Human Metabolome. Molecules. 2021 Mar 5;26(5):1409. doi: 10.3390/molecules26051409. PMID: 33807773; PMCID: PMC7961382. 2. Kim SH, Choo GS, Yoo ES, Woo JS, Han SH, Lee JH, Jung JY. Silymarin induces inhibition of growth and apoptosis through modulation of the MAPK signaling pathway in AGS human gastric cancer cells. Oncol Rep. 2019 Nov;42(5):1904-1914. doi: 10.3892/or.2019.7295. Epub 2019 Aug 28. PMID: 31485597; PMCID: PMC6775811. 3. Bai Y, Wang L, TingYang, Wang L, Ge W. Silymarin ameliorates peritoneal fibrosis by inhibiting the TGF-β/Smad signaling pathway. Naunyn Schmiedebergs Arch Pharmacol. 2023 Oct;396(10):2379-2391. doi: 10.1007/s00210-023-02450-4. Epub 2023 Apr 13. PMID: 37052642. 4. Henriet E, Abdallah F, Laurent Y, Guimpied C, Clement E, Simon M, Pichon C, Baril P. Targeting TGF-β1/miR-21 Pathway in Keratinocytes Reveals Protective Effects of Silymarin on Imiquimod-Induced Psoriasis Mouse Model. JID Innov. 2022 Dec 16;3(3):100175. doi: 10.1016/j.xjidi.2022.100175. PMID: 36968096; PMCID: PMC10034514.

In vitro protocol:

In vivo protocol:

1. Bai Y, Wang L, TingYang, Wang L, Ge W. Silymarin ameliorates peritoneal fibrosis by inhibiting the TGF-β/Smad signaling pathway. Naunyn Schmiedebergs Arch Pharmacol. 2023 Oct;396(10):2379-2391. doi: 10.1007/s00210-023-02450-4. Epub 2023 Apr 13. PMID: 37052642. 2. Henriet E, Abdallah F, Laurent Y, Guimpied C, Clement E, Simon M, Pichon C, Baril P. Targeti1. Sardanelli AM, Isgrò C, Palese LL. SARS-CoV-2 Main Protease Active Site Ligands in the Human Metabolome. Molecules. 2021 Mar 5;26(5):1409. doi: 10.3390/molecules26051409. PMID: 33807773; PMCID: PMC7961382. 2. Kim SH, Choo GS, Yoo ES, Woo JS, Han SH, Lee JH, Jung JY. Silymarin induces inhibition of growth and apoptosis through modulation of the MAPK signaling pathway in AGS human gastric cancer cells. Oncol Rep. 2019 Nov;42(5):1904-1914. doi: 10.3892/or.2019.7295. Epub 2019 Aug 28. PMID: 31485597; PMCID: PMC6775811.ng TGF-β1/miR-21 Pathway in Keratinocytes Reveals Protective Effects of Silymarin on Imiquimod-Induced Psoriasis Mouse Model. JID Innov. 2022 Dec 16;3(3):100175. doi: 10.1016/j.xjidi.2022.100175. PMID: 36968096; PMCID: PMC10034514.

1: Mastron JK, Siveen KS, Sethi G, Bishayee A. Silymarin and hepatocellular carcinoma: a systematic, comprehensive, and critical review. Anticancer Drugs. 2015 Jun;26(5):475-86. doi: 10.1097/CAD.0000000000000211. Review. PubMed PMID: 25603021. 2: Yurtcu E, Darcansoy Iseri O, Iffet Sahin F. Effects of silymarin and silymarin-doxorubicin applications on telomerase activity of human hepatocellular carcinoma cell line HepG2. J BUON. 2015 Mar-Apr;20(2):555-61. PubMed PMID: 26011349. 3: Pérez-H J, Carrillo-S C, García E, Ruiz-Mar G, Pérez-Tamayo R, Chavarría A. Neuroprotective effect of silymarin in a MPTP mouse model of Parkinson's disease. Toxicology. 2014 May 7;319:38-43. doi: 10.1016/j.tox.2014.02.009. Epub 2014 Mar 4. PubMed PMID: 24607817. 4: Zholobenko A, Modriansky M. Silymarin and its constituents in cardiac preconditioning. Fitoterapia. 2014 Sep;97:122-32. doi: 10.1016/j.fitote.2014.05.016. Epub 2014 May 29. Review. PubMed PMID: 24879900. 5: Keshavarz Afshar R, Chaichi MR, Ansari Jovini M, Jahanzad E, Hashemi M. Accumulation of silymarin in milk thistle seeds under drought stress. Planta. 2015 Sep;242(3):539-43. doi: 10.1007/s00425-015-2265-9. Epub 2015 Feb 24. PubMed PMID: 25708739. 6: Li D, Xu D, Wang T, Shen Y, Guo S, Zhang X, Guo L, Li X, Liu L, Wen F. Silymarin attenuates airway inflammation induced by cigarette smoke in mice. Inflammation. 2015 Apr;38(2):871-8. doi: 10.1007/s10753-014-9996-9. PubMed PMID: 25117568. 7: Poruba M, Kazdová L, Oliyarnyk O, Malinská H, Matusková Z, Tozzi di Angelo I, Skop V, Vecera R. Improvement bioavailability of silymarin ameliorates severe dyslipidemia associated with metabolic syndrome. Xenobiotica. 2015;45(9):751-6. doi: 10.3109/00498254.2015.1010633. Epub 2015 Jul 16. PubMed PMID: 26068528. 8: Razavi-Azarkhiavi K, Ali-Omrani M, Solgi R, Bagheri P, Haji-Noormohammadi M, Amani N, Sepand MR. Silymarin alleviates bleomycin-induced pulmonary toxicity and lipid peroxidation in mice. Pharm Biol. 2014 Oct;52(10):1267-71. doi: 10.3109/13880209.2014.889176. Epub 2014 Jul 15. PubMed PMID: 25026360. 9: Wang M, Xie T, Chang Z, Wang L, Xie X, Kou Y, Xu H, Gao X. A New Type of Liquid Silymarin Proliposome Containing Bile Salts: Its Preparation and Improved Hepatoprotective Effects. PLoS One. 2015 Dec 16;10(12):e0143625. doi: 10.1371/journal.pone.0143625. eCollection 2015. PubMed PMID: 26674103; PubMed Central PMCID: PMC4682635. 10: Aller R, Izaola O, Gómez S, Tafur C, González G, Berroa E, Mora N, González JM, de Luis DA. Effect of silymarin plus vitamin E in patients with non-alcoholic fatty liver disease. A randomized clinical pilot study. Eur Rev Med Pharmacol Sci. 2015 Aug;19(16):3118-24. PubMed PMID: 26367736. 11: Cheng KC, Asakawa A, Li YX, Chung HH, Amitani H, Ueki T, Cheng JT, Inui A. Silymarin induces insulin resistance through an increase of phosphatase and tensin homolog in Wistar rats. PLoS One. 2014 Jan 3;9(1):e84550. doi: 10.1371/journal.pone.0084550. eCollection 2014. PubMed PMID: 24404172; PubMed Central PMCID: PMC3880317. 12: Yamsani SK, Yamsani MR. Effect of silymarin pretreatment on the bioavailability of domperidone in healthy human volunteers. Drug Metabol Drug Interact. 2014;29(4):261-7. doi: 10.1515/dmdi-2014-0013. PubMed PMID: 25029082. 13: Evren E, Yurtcu E. In vitro effects on biofilm viability and antibacterial and antiadherent activities of silymarin. Folia Microbiol (Praha). 2015 Jul;60(4):351-6. doi: 10.1007/s12223-015-0399-6. Epub 2015 May 4. PubMed PMID: 25937395. 14: Mata-Santos HA, Dutra FF, Rocha CC, Lino FG, Xavier FR, Chinalia LA, Hossy BH, Castelo-Branco MT, Teodoro AJ, Paiva CN, dos Santos Pyrrho A. Silymarin reduces profibrogenic cytokines and reverses hepatic fibrosis in chronic murine schistosomiasis. Antimicrob Agents Chemother. 2014;58(4):2076-83. doi: 10.1128/AAC.01936-13. Epub 2014 Jan 21. PubMed PMID: 24449779; PubMed Central PMCID: PMC4023717. 15: Chang LW, Hou ML, Tsai TH. Silymarin in liposomes and ethosomes: pharmacokinetics and tissue distribution in free-moving rats by high-performance liquid chromatography-tandem mass spectrometry. J Agric Food Chem. 2014 Dec 3;62(48):11657-65. doi: 10.1021/jf504139g. Epub 2014 Nov 19. PubMed PMID: 25375210. 16: Hwang du H, Kim YI, Cho KH, Poudel BK, Choi JY, Kim DW, Shin YJ, Bae ON, Yousaf AM, Yong CS, Kim JO, Choi HG. A novel solid dispersion system for natural product-loaded medicine: silymarin-loaded solid dispersion with enhanced oral bioavailability and hepatoprotective activity. J Microencapsul. 2014;31(7):619-26. doi: 10.3109/02652048.2014.911375. Epub 2014 Apr 25. PubMed PMID: 24766208. 17: Shangguan M, Lu Y, Qi J, Han J, Tian Z, Xie Y, Hu F, Yuan H, Wu W. Binary lipids-based nanostructured lipid carriers for improved oral bioavailability of silymarin. J Biomater Appl. 2014 Feb;28(6):887-96. doi: 10.1177/0885328213485141. Epub 2013 Sep 5. PubMed PMID: 24008629. 18: Chen CH, Chang CC, Shih TH, Aljuffali IA, Yeh TS, Fang JY. Self-nanoemulsifying drug delivery systems ameliorate the oral delivery of silymarin in rats with Roux-en-Y gastric bypass surgery. Int J Nanomedicine. 2015 Mar 25;10:2403-16. doi: 10.2147/IJN.S79522. eCollection 2015. PubMed PMID: 25848259; PubMed Central PMCID: PMC4381630. 19: Wianowska D, Wiśniewski M. Simplified procedure of silymarin extraction from Silybum marianum L. Gaertner. J Chromatogr Sci. 2015 Feb;53(2):366-72. doi: 10.1093/chromsci/bmu049. Epub 2014 Jun 3. PubMed PMID: 24895445. 20: Snima KS, Arunkumar P, Jayakumar R, Lakshmanan VK. Silymarin encapsulated poly(D,L-lactic-co-glycolic acid) nanoparticles: a prospective candidate for prostate cancer therapy. J Biomed Nanotechnol. 2014 Apr;10(4):559-70. PubMed PMID: 24734508.