Silychristin | CAS#33889-69-9 | Inhibitor

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

MedKoo CAT#: 112087

CAS#: 33889-69-9

Description: Silychristin inhibits monocarboxylate transporter 8 and MCT8-dependent uptake of the thyroid hormone 3,3’,5-triiodo-L-thyronine (T3) in MDCK cells and primary mouse astrocytes.

Chemical Structure

Silychristin

CAS# 33889-69-9

Instruction

Theoretical Analysis

MedKoo Cat#: 112087
Name: Silychristin
CAS#: 33889-69-9
Chemical Formula: C25H22O10
Exact Mass: 482.12
Molecular Weight: 482.440
Elemental Analysis: C, 62.24; H, 4.60; O, 33.16

Price and Availability

Size	Price	Availability
5mg	USD 360	2 Weeks
10mg	USD 690	2 Weeks
25mg	USD 1150	2 Weeks
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: Silychristin; Silychristin A; (+)-Silychristin

IUPAC/Chemical Name: (2R,3R)-3,5,7-trihydroxy-2-((2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzofuran-5-yl)chroman-4-one

InChi Key: BMLIIPOXVWESJG-LMBCONBSSA-N

InChi Code: InChI=1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14-,22+,23+,24-/m1/s1

SMILES Code: OC[C@@H]1C2=CC([C@]3(OC4=CC(O)=CC(O)=C4C([C@@H]3O)=O)[H])=CC(O)=C2O[C@]1(C5=CC(OC)=C(O)C=C5)[H]

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	25.0	51.82
	DMSO	25.0	51.82

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:
In vitro protocol:
In vivo protocol:

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Biedermann D, Buchta M, Holečková V, Sedlák D, Valentová K, Cvačka J, Bednárová L, Křenková A, Kuzma M, Škuta C, Peikerová Ž, Bartůněk P, Křen V. Silychristin: Skeletal Alterations and Biological Activities. J Nat Prod. 2016 Dec 23;79(12):3086-3092. doi: 10.1021/acs.jnatprod.6b00750. Epub 2016 Nov 22. PMID: 28006905.

2: Vavříková E, Gavezzotti P, Purchartová K, Fuksová K, Biedermann D, Kuzma M, Riva S, Křen V. Regioselective alcoholysis of silychristin acetates catalyzed by lipases. Int J Mol Sci. 2015 May 26;16(6):11983-95. doi: 10.3390/ijms160611983. PMID: 26016503; PMCID: PMC4490424.

3: Wang J, Zhang X, Zhang L, Yan T, Wu B, Xu F, Jia Y. Silychristin A activates Nrf2-HO-1/SOD2 pathway to reduce apoptosis and improve GLP-1 production through upregulation of estrogen receptor α in GLUTag cells. Eur J Pharmacol. 2020 Aug 15;881:173236. doi: 10.1016/j.ejphar.2020.173236. Epub 2020 Jun 1. PMID: 32497626.

4: Kato E, Kushibiki N, Satoh H, Kawabata J. Silychristin derivatives conjugated with coniferylalcohols from silymarin and their pancreatic α-amylase inhibitory activity. Nat Prod Res. 2020 Mar;34(6):759-765. doi: 10.1080/14786419.2018.1499639. Epub 2018 Nov 16. PMID: 30445852.

5: Viktorová J, Dobiasová S, Řehořová K, Biedermann D, Káňová K, Šeborová K, Václavíková R, Valentová K, Ruml T, Křen V, Macek T. Antioxidant, Anti- Inflammatory, and Multidrug Resistance Modulation Activity of Silychristin Derivatives. Antioxidants (Basel). 2019 Aug 14;8(8):303. doi: 10.3390/antiox8080303. PMID: 31416138; PMCID: PMC6720199.

6: AbouZid SF, Ahmed HS, Abd El Mageed AMA, Moawad AS, Owis AI, Chen SN, Nachtergael A, McAlpine JB, Friesen JB, Pauli GF. Linear regression analysis of silychristin A, silybin A and silybin B contents in Silybum marianum. Nat Prod Res. 2020 Jan;34(2):305-310. doi: 10.1080/14786419.2018.1527838. Epub 2018 Nov 29. PMID: 30488719.

7: Johannes J, Jayarama-Naidu R, Meyer F, Wirth EK, Schweizer U, Schomburg L, Köhrle J, Renko K. Silychristin, a Flavonolignan Derived From the Milk Thistle, Is a Potent Inhibitor of the Thyroid Hormone Transporter MCT8. Endocrinology. 2016 Apr;157(4):1694-701. doi: 10.1210/en.2015-1933. Epub 2016 Feb 24. PMID: 26910310.

8: Hrčková G, Kubašková TM, Benada O, Kofroňová O, Tumová L, Biedermann D. Differential Effects of the Flavonolignans Silybin, Silychristin and 2,3-Dehydrosilybin on Mesocestoides vogae Larvae (Cestoda) under Hypoxic and Aerobic In Vitro Conditions. Molecules. 2018 Nov 16;23(11):2999. doi: 10.3390/molecules23112999. PMID: 30453549; PMCID: PMC6278466.

9: Smith WA, Lauren DR, Burgess EJ, Perry NB, Martin RJ. A silychristin isomer and variation of flavonolignan levels in milk thistle (Silybum marianum) fruits. Planta Med. 2005 Sep;71(9):877-80. doi: 10.1055/s-2005-864187. PMID: 16206045.

10: Rajnochová Svobodová A, Gabrielová E, Ulrichová J, Zálešák B, Biedermann D, Vostálová J. A pilot study of the UVA-photoprotective potential of dehydrosilybin, isosilybin, silychristin, and silydianin on human dermal fibroblasts. Arch Dermatol Res. 2019 Aug;311(6):477-490. doi: 10.1007/s00403-019-01928-7. Epub 2019 May 11. PMID: 31079190.

11: Lee JI, Hsu BH, Wu D, Barrett JS. Separation and characterization of silybin, isosilybin, silydianin and silychristin in milk thistle extract by liquid chromatography-electrospray tandem mass spectrometry. J Chromatogr A. 2006 May 26;1116(1-2):57-68. doi: 10.1016/j.chroma.2006.03.053. Epub 2006 Apr 24. PMID: 16631762.

12: Koch HP, Ritschel WA. Bioverfügbarkeit von Silymarin, 1. Mitt. Verteilungsvolumina von Silybin, Silydianin und Silychristin aus In-vitro-Daten [Bioavailability of silymarin, I: Volumes of distribution of silybin, silydianin, and silychristin from in-vitro data (author's transl)]. Arch Pharm (Weinheim). 1981 Jun;314(6):515-7. German. doi: 10.1002/ardp.19813140608. PMID: 7283681.

13: Greimel A, Koch H. Hemmung des enzymatischen Abbaus der Indolessigsäure durch Silybin, Silydianin und Silychristin [Inhibition of the enzyme-catalyzed degradation of indole-3-acetic acid by silybin, dilydianin, and Silychristin (author's transl)]. Planta Med. 1977 Dec;32(4):331-41. German. doi: 10.1055/s-0028-1097608. PMID: 594207.

14: Greimel A, Koch H. Peroxidase-Isoenzyme in Kressekeimlingen (Lepidium sativum L.) und ihre Hemmung durch Silybin, Silydianin und Silychristin [Peroxidase isoenzymes in cress seedlings (Lepidium sativum L.) and their inhibition by silybin, silydianin and silychristin]. Experientia. 1977 Dec 15;33(12):1568-9. German. doi: 10.1007/BF01934001. PMID: 590438.

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