Tamarixetin

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

MedKoo CAT#: 464084

CAS#: 603-61-2

Description: 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

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Tamarixetin
CAS# 603-61-2
Instruction

Theoretical Analysis

MedKoo Cat#: 464084
Name: Tamarixetin
CAS#: 603-61-2
Chemical Formula: C16H12O7
Exact Mass: 316.06
Molecular Weight: 316.265
Elemental Analysis: C, 60.76; H, 3.82; O, 35.41

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.