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MedKoo Cat#: 112068 | Name: Matairesinol
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Description:

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

Matairesinol reduces LPS-induced production of nitric oxide (NO) and prostaglandin E2. Matairesinol is cytotoxic to colon 26 cancer cells (LC50 = 9 µg/ml) and reduces neurotoxicity in neural PC12 cells induced by oxaliplatin.

Chemical Structure

Matairesinol
Matairesinol
CAS#580-72-3

Theoretical Analysis

MedKoo Cat#: 112068

Name: Matairesinol

CAS#: 580-72-3

Chemical Formula: C20H22O6

Exact Mass: 358.1416

Molecular Weight: 358.39

Elemental Analysis: C, 67.03; H, 6.19; O, 26.78

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
(–)-Matairesinol; Matairesinol
IUPAC/Chemical Name
(3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
InChi Key
MATGKVZWFZHCLI-LSDHHAIUSA-N
InChi Code
InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1
SMILES Code
OC1=C(C=C(C=C1)C[C@@H]2[C@H](COC2=O)CC3=CC(OC)=C(C=C3)O)OC
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
Solvent mg/mL mM
Solubility
DMF 30.0 83.71
DMSO 30.0 83.71
Ethanol 2.0 5.58
DMSO:PBS (pH: 7.2) (1:4) 0.3 0.70
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 358.39 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: Mahajan M, Suryavanshi S, Bhowmick S, Alasmary FA, Almutairi TM, Islam MA, Kaul-Ghanekar R. Matairesinol, an active constituent of HC9 polyherbal formulation, exhibits HDAC8 inhibitory and anticancer activity. Biophys Chem. 2021 Jun;273:106588. doi: 10.1016/j.bpc.2021.106588. Epub 2021 Apr 2. PMID: 33848944. 2: Li X, Gao Q, Yang L, Han M, Zhou C, Mu H. Matairesinol ameliorates experimental autoimmune uveitis by suppression of IRBP-specific Th17 cells. J Neuroimmunol. 2020 Aug 15;345:577286. doi: 10.1016/j.jneuroim.2020.577286. Epub 2020 Jun 6. PMID: 32559555. 3: Xu P, Huang MW, Xiao CX, Long F, Wang Y, Liu SY, Jia WW, Wu WJ, Yang D, Hu JF, Liu XH, Zhu YZ. Matairesinol Suppresses Neuroinflammation and Migration Associated with Src and ERK1/2-NF-κB Pathway in Activating BV2 Microglia. Neurochem Res. 2017 Oct;42(10):2850-2860. doi: 10.1007/s11064-017-2301-1. Epub 2017 May 17. PMID: 28512713. 4: Choi SW, Park KI, Yeon JT, Ryu BJ, Kim KJ, Kim SH. Anti-osteoclastogenic activity of matairesinol via suppression of p38/ERK-NFATc1 signaling axis. BMC Complement Altern Med. 2014 Jan 21;14:35. doi: 10.1186/1472-6882-14-35. PMID: 24444335; PMCID: PMC3903021. 5: Wu Q, Wang Y, Li Q. Matairesinol exerts anti-inflammatory and antioxidant effects in sepsis-mediated brain injury by repressing the MAPK and NF-κB pathways through up-regulating AMPK. Aging (Albany NY). 2021 Oct 27;13(20):23780-23795. doi: 10.18632/aging.. Epub 2021 Oct 27. PMID: 34705665; PMCID: PMC8580336. 6: Yamawaki M, Nishi K, Nishimoto S, Yamauchi S, Akiyama K, Kishida T, Maruyama M, Nishiwaki H, Sugahara T. Immunomodulatory effect of (--)-matairesinol in vivo and ex vivo. Biosci Biotechnol Biochem. 2011;75(5):859-63. doi: 10.1271/bbb.100781. Epub 2011 May 20. PMID: 21597179. 7: Lee B, Kim KH, Jung HJ, Kwon HJ. Matairesinol inhibits angiogenesis via suppression of mitochondrial reactive oxygen species. Biochem Biophys Res Commun. 2012 Apr 27;421(1):76-80. doi: 10.1016/j.bbrc.2012.03.114. Epub 2012 Mar 28. PMID: 22483751. 8: Su S, Cheng X, Wink M. Cytotoxicity of arctigenin and matairesinol against the T-cell lymphoma cell line CCRF-CEM. J Pharm Pharmacol. 2015 Sep;67(9):1316-23. doi: 10.1111/jphp.12426. Epub 2015 Apr 29. PMID: 25922263. 9: Niemeyer HB, Honig DM, Kulling SE, Metzler M. Studies on the metabolism of the plant lignans secoisolariciresinol and matairesinol. J Agric Food Chem. 2003 Oct 8;51(21):6317-25. doi: 10.1021/jf030263n. PMID: 14518962. 10: Kuo HJ, Wei ZY, Lu PC, Huang PL, Lee KT. Bioconversion of pinoresinol into matairesinol by use of recombinant Escherichia coli. Appl Environ Microbiol. 2014 May;80(9):2687-92. doi: 10.1128/AEM.03397-13. Epub 2014 Feb 21. PMID: 24561584; PMCID: PMC3993289. 11: Kawahara S, Iwata I, Fujita E, Yamawaki M, Nishiwaki H, Sugahara T, Yamauchi S, Akiyama K, Kishida T. IgE-suppressive activity of (-)-matairesinol and its structure-activity relationship. Biosci Biotechnol Biochem. 2010;74(9):1878-83. doi: 10.1271/bbb.100275. Epub 2010 Sep 7. PMID: 20834158. 12: Sung YY, Lee AY, Kim HK. Forsythia suspensa fruit extracts and the constituent matairesinol confer anti-allergic effects in an allergic dermatitis mouse model. J Ethnopharmacol. 2016 Jul 1;187:49-56. doi: 10.1016/j.jep.2016.04.015. Epub 2016 Apr 13. PMID: 27085937. 13: Brito DCC, Silva IP, Ferreira ACA, Sá NAR, Guedes MIF, Rodrigues APR, Santos RR, Figueiredo JR. Effects of in vitro exposure of sheep ovarian tissue to zearalenone and matairesinol on preantral follicles. Zygote. 2022 Jun;30(3):419-422. doi: 10.1017/S0967199421000794. Epub 2021 Oct 25. PMID: 34689852. 14: Eklund P, Lindholm A, Mikkola JP, Smeds A, Lehtilä R, Sjöholm R. Synthesis of (-)-matairesinol, (-)-enterolactone, and (-)-enterodiol from the natural lignan hydroxymatairesinol. Org Lett. 2003 Feb 20;5(4):491-3. doi: 10.1021/ol0273598. PMID: 12583751. 15: Umezawa T, Davin LB, Lewis NG. Formation of lignans (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia cell-free extracts. J Biol Chem. 1991 Jun 5;266(16):10210-7. PMID: 2037574. 16: Yang B, Linko AM, Adlercreutz H, Kallio H. Secoisolariciresinol and matairesinol of sea buckthorn (Hippophaë rhamnoides L.) berries of different subspecies and harvesting times. J Agric Food Chem. 2006 Oct 18;54(21):8065-70. doi: 10.1021/jf061904s. PMID: 17032010. 17: Kim CY, Ahn MJ, Kim J. A preparative isolation and purification of arctigenin and matairesinol from Forsythia koreana by centrifugal partition chromatography. J Sep Sci. 2006 Mar;29(5):656-9. doi: 10.1002/jssc.200500316. PMID: 16605084. 18: Pajari AM, Smeds AI, Oikarinen SI, Eklund PC, Sjöholm RE, Mutanen M. The plant lignans matairesinol and secoisolariciresinol administered to Min mice do not protect against intestinal tumor formation. Cancer Lett. 2006 Feb 28;233(2):309-14. doi: 10.1016/j.canlet.2005.03.061. Epub 2005 Jul 5. PMID: 16000235. 19: Yokoyama T, Okano M, Noshita T, Funayama S, Ohtsuki K. Characterization of (-)-matairesinol as a potent inhibitor of casein kinase I in vitro. Biol Pharm Bull. 2003 Mar;26(3):371-4. doi: 10.1248/bpb.26.371. PMID: 12612451. 20: Yamauchi S, Sugahara T, Nakashima Y, Okada A, Akiyama K, Kishida T, Maruyama M, Masuda T. Radical and superoxide scavenging activities of matairesinol and oxidized matairesinol. Biosci Biotechnol Biochem. 2006 Aug;70(8):1934-40. doi: 10.1271/bbb.60096. PMID: 16926506.