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MedKoo Cat#: 535219 | Name: Silybin B

Description:

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

Silybin B is a natural multidrug resistance (MDR) modulator, inhibiting P-glycoprotein (P-gp) ATPase activity and regulating ATP-binding cassette (ABC) protein expression,also significantly inhibiting Aβ aggregation in vitro and exerting neuroprotective properties in vivo.

Chemical Structure

Silybin B
Silybin B
CAS#142797-34-0

Theoretical Analysis

MedKoo Cat#: 535219

Name: Silybin B

CAS#: 142797-34-0

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

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Silybin B
IUPAC/Chemical Name
(2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-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
O=C1[C@H](O)[C@@H](C2=CC=C(O[C@@H](CO)[C@H](C3=CC=C(O)C(OC)=C3)O4)C4=C2)OC5=C1C(O)=CC(O)=C5
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
2934.99.9001
More Info

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.

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
1: Li WY, Yu G, Hogan RM, Mohandas R, Frye RF, Gumpricht E, Markowitz JS. Relative Bioavailability of Silybin A and Silybin B From 2 Multiconstituent Dietary Supplement Formulations Containing Milk Thistle Extract: A Single-dose Study. Clin Ther. 2018 Jan;40(1):103-113.e1. doi: 10.1016/j.clinthera.2017.11.013. Epub 2017 Dec 19. PMID: 29273470; PMCID: PMC6037411. 2: Federico A, Dallio M, Loguercio C. Silymarin/Silybin and Chronic Liver Disease: A Marriage of Many Years. Molecules. 2017 Jan 24;22(2):191. doi: 10.3390/molecules22020191. PMID: 28125040; PMCID: PMC6155865. 3: Bijak M. Silybin, a Major Bioactive Component of Milk Thistle (Silybum marianum L. Gaernt.)-Chemistry, Bioavailability, and Metabolism. Molecules. 2017 Nov 10;22(11):1942. doi: 10.3390/molecules22111942. PMID: 29125572; PMCID: PMC6150307. 4: Ou Q, Weng Y, Wang S, Zhao Y, Zhang F, Zhou J, Wu X. Silybin Alleviates Hepatic Steatosis and Fibrosis in NASH Mice by Inhibiting Oxidative Stress and Involvement with the Nf-κB Pathway. Dig Dis Sci. 2018 Dec;63(12):3398-3408. doi: 10.1007/s10620-018-5268-0. Epub 2018 Sep 6. PMID: 30191499. 5: Biedermann D, Vavříková E, Cvak L, Křen V. Chemistry of silybin. Nat Prod Rep. 2014 Sep;31(9):1138-57. doi: 10.1039/c3np70122k. PMID: 24977260. 6: Méndez-Sánchez N, Dibildox-Martinez M, Sosa-Noguera J, Sánchez-Medal R, Flores-Murrieta FJ. Superior silybin bioavailability of silybin- phosphatidylcholine complex in oily-medium soft-gel capsules versus conventional silymarin tablets in healthy volunteers. BMC Pharmacol Toxicol. 2019 Jan 11;20(1):5. doi: 10.1186/s40360-018-0280-8. Erratum in: BMC Pharmacol Toxicol. 2019 Feb 22;20(1):14. PMID: 30635055; PMCID: PMC6330464. 7: Zhang B, Wang B, Cao S, Wang Y, Wu D. Silybin attenuates LPS-induced lung injury in mice by inhibiting NF-κB signaling and NLRP3 activation. Int J Mol Med. 2017 May;39(5):1111-1118. doi: 10.3892/ijmm.2017.2935. Epub 2017 Mar 27. PMID: 28350048; PMCID: PMC5403282. 8: Anfuso B, Giraudi PJ, Tiribelli C, Rosso N. Silybin Modulates Collagen Turnover in an In Vitro Model of NASH. Molecules. 2019 Apr 2;24(7):1280. doi: 10.3390/molecules24071280. PMID: 30986937; PMCID: PMC6479571. 9: Abenavoli L, Izzo AA, Milić N, Cicala C, Santini A, Capasso R. Milk thistle (Silybum marianum): A concise overview on its chemistry, pharmacological, and nutraceutical uses in liver diseases. Phytother Res. 2018 Nov;32(11):2202-2213. doi: 10.1002/ptr.6171. Epub 2018 Aug 6. PMID: 30080294. 10: Křen V, Marhol P, Purchartová K, Gabrielová E, Modrianský M. Biotransformation of silybin and its congeners. Curr Drug Metab. 2013 Dec;14(10):1009-21. doi: 10.2174/1389200214666131118234507. PMID: 24261705. 11: Zhang J, Luan Q, Liu Y, Lee DY, Wang Z. A comparison of the diastereoisomers, silybin A and silybin B, on the induction of apoptosis in K562 cells. Nat Prod Commun. 2011 Nov;6(11):1653-6. PMID: 22224281. 12: Bi X, Yuan Z, Qu B, Zhou H, Liu Z, Xie Y. Piperine enhances the bioavailability of silybin via inhibition of efflux transporters BCRP and MRP2. Phytomedicine. 2019 Feb 15;54:98-108. doi: 10.1016/j.phymed.2018.09.217. Epub 2018 Sep 28. PMID: 30668388. 13: Zappavigna S, Vanacore D, Lama S, Potenza N, Russo A, Ferranti P, Dallio M, Federico A, Loguercio C, Sperlongano P, Caraglia M, Stiuso P. Silybin-Induced Apoptosis Occurs in Parallel to the Increase of Ceramides Synthesis and miRNAs Secretion in Human Hepatocarcinoma Cells. Int J Mol Sci. 2019 May 3;20(9):2190. doi: 10.3390/ijms20092190. PMID: 31058823; PMCID: PMC6539179. 14: Sy-Cordero AA, Graf TN, Runyon SP, Wani MC, Kroll DJ, Agarwal R, Brantley SJ, Paine MF, Polyak SJ, Oberlies NH. Enhanced bioactivity of silybin B methylation products. Bioorg Med Chem. 2013 Feb 1;21(3):742-7. doi: 10.1016/j.bmc.2012.11.035. Epub 2012 Dec 5. PMID: 23260576; PMCID: PMC3630461. 15: Xie Y, Zhang D, Zhang J, Yuan J. Metabolism, Transport and Drug-Drug Interactions of Silymarin. Molecules. 2019 Oct 14;24(20):3693. doi: 10.3390/molecules24203693. PMID: 31615114; PMCID: PMC6832356. 16: Pignatelli P, Carnevale R, Menichelli D. Silybin and metabolic disorders. Intern Emerg Med. 2019 Jan;14(1):1-3. doi: 10.1007/s11739-018-1968-x. Epub 2018 Oct 17. PMID: 30327932. 17: Abenavoli L, Capasso R, Milic N, Capasso F. Milk thistle in liver diseases: past, present, future. Phytother Res. 2010 Oct;24(10):1423-32. doi: 10.1002/ptr.3207. PMID: 20564545. 18: Li Y, Yang D, Wang Y, Li Z, Zhu C. Co-delivery doxorubicin and silybin for anti-hepatoma via enhanced oral hepatic-targeted efficiency. Int J Nanomedicine. 2018 Dec 28;14:301-315. doi: 10.2147/IJN.S187888. PMID: 30643408; PMCID: PMC6314320. 19: Federico A, Dallio M, Masarone M, Gravina AG, Di Sarno R, Tuccillo C, Cossiga V, Lama S, Stiuso P, Morisco F, Persico M, Loguercio C. Evaluation of the Effect Derived from Silybin with Vitamin D and Vitamin E Administration on Clinical, Metabolic, Endothelial Dysfunction, Oxidative Stress Parameters, and Serological Worsening Markers in Nonalcoholic Fatty Liver Disease Patients. Oxid Med Cell Longev. 2019 Oct 15;2019:8742075. doi: 10.1155/2019/8742075. PMID: 31737175; PMCID: PMC6815609. 20: Purchartová K, Engels L, Marhol P, Sulc M, Kuzma M, Slámová K, Elling L, Křen V. Enzymatic preparation of silybin phase II metabolites: sulfation using aryl sulfotransferase from rat liver. Appl Microbiol Biotechnol. 2013 Dec;97(24):10391-8. doi: 10.1007/s00253-013-4794-0. Epub 2013 Mar 14. PMID: 23494622.

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