MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 464084 | Name: Tamarixetin

Description:

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

Tamarixetin is a monomethoxyflavone that is quercetin methylated at position O-4'. It is isolated from Cyperus teneriffae and has a role as a metabolite and an antioxidant. It is a 7-hydroxyflavonol, a monomethoxyflavone and a tetrahydroxyflavone.

Chemical Structure

Tamarixetin
Tamarixetin
CAS#603-61-2

Theoretical Analysis

MedKoo Cat#: 464084

Name: Tamarixetin

CAS#: 603-61-2

Chemical Formula: C16H12O7

Exact Mass: 316.0583

Molecular Weight: 316.27

Elemental Analysis: C, 60.76; H, 3.82; O, 35.41

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Tamarixetin;
IUPAC/Chemical Name
3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
InChi Key
FPLMIPQZHHQWHN-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H12O7/c1-22-11-3-2-7(4-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
SMILES Code
COc1c(O)cc(C2=C(C(c3c(O2)cc(O)cc3O)=O)O)cc1
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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
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 316.27 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: Darsandhari S, Dhakal D, Shrestha B, Lee S, Jung N, Jung HJ, Sohng JK. Biosynthesis of bioactive tamarixetin in recombinant Escherichia coli. Biotechnol Appl Biochem. 2020 May 19. doi: 10.1002/bab.1958. Epub ahead of print. PMID: 32430989. 2: Park HJ, Lee SJ, Cho J, Gharbi A, Han HD, Kang TH, Kim Y, Lee Y, Park WS, Jung ID, Park YM. Tamarixetin Exhibits Anti-inflammatory Activity and Prevents Bacterial Sepsis by Increasing IL-10 Production. J Nat Prod. 2018 Jun 22;81(6):1435-1443. doi: 10.1021/acs.jnatprod.8b00155. Epub 2018 May 31. PMID: 29851490. 3: Xu J, Cai X, Teng S, Lu J, Zhou Y, Wang X, Meng Z. The Pro-Apoptotic Activity of Tamarixetin on Liver Cancer Cells Via Regulation Mitochondrial Apoptotic Pathway. Appl Biochem Biotechnol. 2019 Oct;189(2):647-660. doi: 10.1007/s12010-019-03033-x. Epub 2019 May 16. PMID: 31093908. 4: Shen J, Jia Q, Huang X, Yao G, Ma W, Chang Y, Ouyang H, He J. Study on Pharmacokinetic and Bioavailability of Tamarixetin after Intravenous and Oral Administration to Rats. Evid Based Complement Alternat Med. 2019 Dec 10;2019:6932053. doi: 10.1155/2019/6932053. PMID: 31885660; PMCID: PMC6925790. 5: Fan C, Li Y, Yang H, Cui Y, Wang H, Zhou H, Zhang J, Du B, Zhai Q, Wu D, Chen X, Guo H. Tamarixetin protects against cardiac hypertrophy via inhibiting NFAT and AKT pathway. J Mol Histol. 2019 Aug;50(4):343-354. doi: 10.1007/s10735-019-09831-1. Epub 2019 May 20. PMID: 31111288. 6: Shaji SK, G D, Sunilkumar D, Pandurangan N, Kumar GB, Nair BG. Nuclear factor-κB plays an important role in Tamarixetin-mediated inhibition of matrix metalloproteinase-9 expression. Eur J Pharmacol. 2021 Feb 15;893:173808. doi: 10.1016/j.ejphar.2020.173808. Epub 2020 Dec 17. PMID: 33345858. 7: Yadav DK, Bharitkar YP, Hazra A, Pal U, Verma S, Jana S, Singh UP, Maiti NC, Mondal NB, Swarnakar S. Tamarixetin 3-O-β-d-Glucopyranoside from Azadirachta indica Leaves: Gastroprotective Role through Inhibition of Matrix Metalloproteinase-9 Activity in Mice. J Nat Prod. 2017 May 26;80(5):1347-1353. doi: 10.1021/acs.jnatprod.6b00957. Epub 2017 May 11. PMID: 28493718. 8: Hayamizu K, Morimoto S, Nonaka M, Hoka S, Sasaguri T. Cardiotonic actions of quercetin and its metabolite tamarixetin through a digitalis-like enhancement of Ca2+ transients. Arch Biochem Biophys. 2018 Jan 1;637:40-47. doi: 10.1016/j.abb.2017.11.009. Epub 2017 Nov 21. PMID: 29169900. 9: Peng W, Li Y, Zhu C, Han X, Yu B. Synthesis of tamarixetin and isorhamnetin 3-O-neohesperidoside. Carbohydr Res. 2005 Jul 25;340(10):1682-8. doi: 10.1016/j.carres.2005.04.021. PMID: 15927167. 10: Nicolini F, Burmistrova O, Marrero MT, Torres F, Hernández C, Quintana J, Estévez F. Induction of G2/M phase arrest and apoptosis by the flavonoid tamarixetin on human leukemia cells. Mol Carcinog. 2014 Dec;53(12):939-50. doi: 10.1002/mc.22055. Epub 2013 Jun 13. PMID: 23765509. 11: Zhu C, Peng W, Li Y, Han X, Yu B. Synthesis of 3-O-(beta-D- xylopyranosyl-(1-->2)-beta-D-glucopyranosyl)-3'-O-(beta-D- glucopyranosyl)tamarixetin, the putative structure of aescuflavoside A from the seeds of Aesculus chinensis. Carbohydr Res. 2006 Jun 12;341(8):1047-51. doi: 10.1016/j.carres.2006.02.036. Epub 2006 Apr 3. PMID: 16580652. 12: Moalin M, van Strijdonck GP, Bast A, Haenen GR. Competition between ascorbate and glutathione for the oxidized form of methylated quercetin metabolites and analogues: tamarixetin, 4'O-methylquercetin, has the lowest thiol reactivity. J Agric Food Chem. 2012 Sep 12;60(36):9292-7. doi: 10.1021/jf302068v. Epub 2012 Aug 27. PMID: 22860763. 13: Sakai M, Ohnishi K, Masuda M, Ohminami H, Yamanaka-Okumura H, Hara T, Taketani Y. Isorhamnetin, a 3'-methoxylated flavonol, enhances the lysosomal proteolysis in J774.1 murine macrophages in a TFEB-independent manner. Biosci Biotechnol Biochem. 2020 Jun;84(6):1221-1231. doi: 10.1080/09168451.2020.1727309. Epub 2020 Feb 12. PMID: 32046625. 14: Dragoni S, Gee J, Bennett R, Valoti M, Sgaragli G. Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro. Br J Pharmacol. 2006 Apr;147(7):765-71. doi: 10.1038/sj.bjp.0706662. PMID: 16444288; PMCID: PMC1760706. 15: Burak C, Wolffram S, Zur B, Langguth P, Fimmers R, Alteheld B, Stehle P, Egert S. Effect of alpha-linolenic acid in combination with the flavonol quercetin on markers of cardiovascular disease risk in healthy, non-obese adults: A randomized, double-blinded placebo-controlled crossover trial. Nutrition. 2019 Feb;58:47-56. doi: 10.1016/j.nut.2018.06.012. Epub 2018 Jul 12. PMID: 30278429. 16: Stainer AR, Sasikumar P, Bye AP, Unsworth AJ, Holbrook LM, Tindall M, Lovegrove JA, Gibbins JM. The Metabolites of the Dietary Flavonoid Quercetin Possess Potent Antithrombotic Activity, and Interact with Aspirin to Enhance Antiplatelet Effects. TH Open. 2019 Jul 30;3(3):e244-e258. doi: 10.1055/s-0039-1694028. PMID: 31367693; PMCID: PMC6667742. 17: Ashmawy NS, Gad HA, Al-Musayeib N, El-Ahmady SH, Ashour ML, Singab ANB. Phytoconstituents from Polyscias guilfoylei leaves with histamine-release inhibition activity. Z Naturforsch C J Biosci. 2019 May 27;74(5-6):145-150. doi: 10.1515/znc-2018-0167. PMID: 30721147. 18: Lau AJ, Chang TK. 3-Hydroxyflavone and structural analogues differentially activate pregnane X receptor: Implication for inflammatory bowel disease. Pharmacol Res. 2015 Oct;100:64-72. doi: 10.1016/j.phrs.2015.07.031. Epub 2015 Jul 31. PMID: 26238175. 19: Lemmens KJ, Vrolijk MF, Bouwman FG, van der Vijgh WJ, Bast A, Haenen GR. The minor structural difference between the antioxidants quercetin and 4'O-methylquercetin has a major impact on their selective thiol toxicity. Int J Mol Sci. 2014 Apr 30;15(5):7475-84. doi: 10.3390/ijms15057475. PMID: 24786288; PMCID: PMC4057684. 20: Eseberri I, Miranda J, Lasa A, Mosqueda-Solís A, González-Manzano S, Santos- Buelga C, Portillo MP. Effects of Quercetin Metabolites on Triglyceride Metabolism of 3T3-L1 Preadipocytes and Mature Adipocytes. Int J Mol Sci. 2019 Jan 11;20(2):264. doi: 10.3390/ijms20020264. PMID: 30641871; PMCID: PMC6359054.

View History

Vorolanib

Vorolanib

Featured