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MedKoo Cat#: 530370 | Name: TMS
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Description:

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

TMS, also knonw as Tetramethoxystilbene, is a potent and selective inhibitor of CYP1B1, with an IC50 of 6 nM. TMS is also a resveratrol analogue, which suppressed induced differentiation of C3H10T1/2 cells. TMS can suppress adipogenic differentiation of C3H10T1/2 cells by inhibiting PPARγ. 2,3',4,5'-Tetramethoxystilbene prevents deoxycorticosterone-salt-induced hypertension: contribution of cytochrome P-450 1B1.

Chemical Structure

TMS
TMS
CAS#24144-92-1

Theoretical Analysis

MedKoo Cat#: 530370

Name: TMS

CAS#: 24144-92-1

Chemical Formula: C18H20O4

Exact Mass: 300.1362

Molecular Weight: 300.35

Elemental Analysis: C, 71.98; H, 6.71; O, 21.31

Price and Availability

Size Price Availability Quantity
200mg USD 250.00 2 Weeks
500mg USD 550.00 2 Weeks
1g USD 950.00 2 Weeks
2g USD 1,650.00 2 Weeks
5g USD 3,650.00 2 Weeks
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Related CAS #
No Data
Synonym
TMS; 2,3',4,5'-Tetramethoxystilbene
IUPAC/Chemical Name
(E)-1-(3,5-dimethoxystyryl)-2,4-dimethoxybenzene
InChi Key
JDBCWSHYEQUBLW-AATRIKPKSA-N
InChi Code
InChI=1S/C18H20O4/c1-19-15-8-7-14(18(12-15)22-4)6-5-13-9-16(20-2)11-17(10-13)21-3/h5-12H,1-4H3/b6-5+
SMILES Code
COC1=CC(OC)=CC(/C=C/C2=CC=C(OC)C=C2OC)=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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 300.35 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: Einem Lindeman T, Poirier MC, Divi RL. The resveratrol analogue, 2,3',4,5'-tetramethoxystilbene, does not inhibit CYP gene expression, enzyme activity and benzo[a]pyrene-DNA adduct formation in MCF-7 cells exposed to benzo[a]pyrene. Mutagenesis. 2011 Sep;26(5):629-35. doi: 10.1093/mutage/ger024. PubMed PMID: 21669939; PubMed Central PMCID: PMC3162036. 2: Sahan-Firat S, Jennings BL, Yaghini FA, Song CY, Estes AM, Fang XR, Farjana N, Khan AI, Malik KU. 2,3',4,5'-Tetramethoxystilbene prevents deoxycorticosterone-salt-induced hypertension: contribution of cytochrome P-450 1B1. Am J Physiol Heart Circ Physiol. 2010 Dec;299(6):H1891-901. doi: 10.1152/ajpheart.00655.2010. PubMed PMID: 20852048; PubMed Central PMCID: PMC3006285. 3: Lin HS, Choo QY, Ho PC. Quantification of oxyresveratrol analog trans-2,4,3',5'-tetramethoxystilbene in rat plasma by a rapid HPLC method: application in a pre-clinical pharmacokinetic study. Biomed Chromatogr. 2010 Dec;24(12):1373-8. doi: 10.1002/bmc.1454. PubMed PMID: 21077256. 4: Kim SW, Jung HK, Kim MY. Induction of p27(kip1) by 2,4,3',5'- tetramethoxystilbene is regulated by protein phosphatase 2A-dependent Akt dephosphorylation in PC-3 prostate cancer cells. Arch Pharm Res. 2008 Sep;31(9):1187-94. PubMed PMID: 18816901. 5: Chun YJ, Lee SK, Kim MY. Modulation of human cytochrome P450 1B1 expression by 2,4,3',5'-tetramethoxystilbene. Drug Metab Dispos. 2005 Dec;33(12):1771-6. PubMed PMID: 16120791. 6: Maayah ZH, Althurwi HN, Abdelhamid G, Lesyk G, Jurasz P, El-Kadi AO. CYP1B1 inhibition attenuates doxorubicin-induced cardiotoxicity through a mid-chain HETEs-dependent mechanism. Pharmacol Res. 2016 Mar;105:28-43. doi: 10.1016/j.phrs.2015.12.016. PubMed PMID: 26772815. 7: Jennings BL, Sahan-Firat S, Estes AM, Das K, Farjana N, Fang XR, Gonzalez FJ, Malik KU. Cytochrome P450 1B1 contributes to angiotensin II-induced hypertension and associated pathophysiology. Hypertension. 2010 Oct;56(4):667-74. doi: 10.1161/HYPERTENSIONAHA.110.154518. PubMed PMID: 20805442; PubMed Central PMCID: PMC2946077. 8: White K, Johansen AK, Nilsen M, Ciuclan L, Wallace E, Paton L, Campbell A, Morecroft I, Loughlin L, McClure JD, Thomas M, Mair KM, MacLean MR. Activity of the estrogen-metabolizing enzyme cytochrome P450 1B1 influences the development of pulmonary arterial hypertension. Circulation. 2012 Aug 28;126(9):1087-98. doi: 10.1161/CIRCULATIONAHA.111.062927. PubMed PMID: 22859684. 9: Kim T, Park H, Yue W, Wang JP, Atkins KA, Zhang Z, Rogan EG, Cavalieri EL, Mohammad KS, Kim S, Santen RJ, Aiyar SE. Tetra-methoxystilbene modulates ductal growth of the developing murine mammary gland. Breast Cancer Res Treat. 2011 Apr;126(3):779-89. doi: 10.1007/s10549-010-1301-5. PubMed PMID: 21170676; PubMed Central PMCID: PMC4443710. 10: Jennings BL, Montanez DE, May ME Jr, Estes AM, Fang XR, Yaghini FA, Kanu A, Malik KU. Cytochrome P450 1B1 contributes to increased blood pressure and cardiovascular and renal dysfunction in spontaneously hypertensive rats. Cardiovasc Drugs Ther. 2014 Apr;28(2):145-61. doi: 10.1007/s10557-014-6510-4. PubMed PMID: 24477449; PubMed Central PMCID: PMC4335675. 11: Divi RL, Luch A, Verma M, Mahadevan B. CYP1B1 detection. Curr Protoc Toxicol. 2012 Feb;Chapter 4:Unit 4.38. doi: 10.1002/0471140856.tx0438s51. PubMed PMID: 22511118. 12: Jennings BL, Anderson LJ, Estes AM, Fang XR, Song CY, Campbell WB, Malik KU. Involvement of cytochrome P-450 1B1 in renal dysfunction, injury, and inflammation associated with angiotensin II-induced hypertension in rats. Am J Physiol Renal Physiol. 2012 Feb 15;302(4):F408-20. doi: 10.1152/ajprenal.00542.2011. PubMed PMID: 22088434; PubMed Central PMCID: PMC3289420. 13: Rahman M, Hayes Sutter C, Emmert GL, Sutter TR. Regioselective 2-hydroxylation of 17beta-estradiol by rat cytochrome P4501B1. Toxicol Appl Pharmacol. 2006 Nov 1;216(3):469-78. PubMed PMID: 16893557. 14: Aiyar SE, Park H, Aldo PB, Mor G, Gildea JJ, Miller AL, Thompson EB, Castle JD, Kim S, Santen RJ. TMS, a chemically modified herbal derivative of resveratrol, induces cell death by targeting Bax. Breast Cancer Res Treat. 2010 Nov;124(1):265-77. doi: 10.1007/s10549-010-0903-2. PubMed PMID: 20490654. 15: Song CY, Ghafoor K, Ghafoor HU, Khan NS, Thirunavukkarasu S, Jennings BL, Estes AM, Zaidi S, Bridges D, Tso P, Gonzalez FJ, Malik KU. Cytochrome P450 1B1 Contributes to the Development of Atherosclerosis and Hypertension in Apolipoprotein E-Deficient Mice. Hypertension. 2016 Jan;67(1):206-13. doi: 10.1161/HYPERTENSIONAHA.115.06427. PubMed PMID: 26573711; PubMed Central PMCID: PMC4672747. 16: Yaghini FA, Song CY, Lavrentyev EN, Ghafoor HU, Fang XR, Estes AM, Campbell WB, Malik KU. Angiotensin II-induced vascular smooth muscle cell migration and growth are mediated by cytochrome P450 1B1-dependent superoxide generation. Hypertension. 2010 Jun;55(6):1461-7. doi: 10.1161/HYPERTENSIONAHA.110.150029. PubMed PMID: 20439821; PubMed Central PMCID: PMC2916227. 17: Chiaro CR, Patel RD, Marcus CB, Perdew GH. Evidence for an aryl hydrocarbon receptor-mediated cytochrome p450 autoregulatory pathway. Mol Pharmacol. 2007 Nov;72(5):1369-79. PubMed PMID: 17720764. 18: Thirunavukkarasu S, Khan NS, Song CY, Ghafoor HU, Brand DD, Gonzalez FJ, Malik KU. Cytochrome P450 1B1 Contributes to the Development of Angiotensin II-Induced Aortic Aneurysm in Male Apoe(-/-) Mice. Am J Pathol. 2016 Aug;186(8):2204-19. doi: 10.1016/j.ajpath.2016.04.005. PubMed PMID: 27301358; PubMed Central PMCID: PMC4973656. 19: Likhitwitayawuid K, Sornsute A, Sritularak B, Ploypradith P. Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. Bioorg Med Chem Lett. 2006 Nov 1;16(21):5650-3. PubMed PMID: 16919455. 20: Johansen AK, Dean A, Morecroft I, Hood K, Nilsen M, Loughlin L, Anagnostopoulou A, Touyz RM, White K, MacLean MR. The serotonin transporter promotes a pathological estrogen metabolic pathway in pulmonary hypertension via cytochrome P450 1B1. Pulm Circ. 2016 Mar;6(1):82-92. doi: 10.1086/685023. PubMed PMID: 27162617; PubMed Central PMCID: PMC4860551.

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CP-91149

CP-91149

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