MedKoo Cat#: 146193 | Name: Centaureidin

Description:

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

Centaureidin is a flavonoid compound primarily found in plants of the Centaurea genus, known for its anti-inflammatory, antioxidant, and antimicrobial properties. It exerts its effects by scavenging free radicals and modulating key inflammatory pathways, such as inhibiting the activation of NF-κB and the production of pro-inflammatory cytokines. Centaureidin has potential applications in treating inflammatory conditions, infections, and oxidative stress-related diseases. Its bioactivity makes it a candidate for developing natural therapeutic agents for conditions like arthritis, skin disorders, and microbial infections.

Chemical Structure

Centaureidin
Centaureidin
CAS#17313-52-9

Theoretical Analysis

MedKoo Cat#: 146193

Name: Centaureidin

CAS#: 17313-52-9

Chemical Formula: C18H16O8

Exact Mass: 360.0845

Molecular Weight: 360.32

Elemental Analysis: C, 60.00; H, 4.48; O, 35.52

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.
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Related CAS #
No Data
Synonym
Centaureidin;
IUPAC/Chemical Name
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-chromen-4-one
InChi Key
BZXULYMZYPRZOG-UHFFFAOYSA-N
InChi Code
1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3
SMILES Code
COC1=CC=C(C=C1O)C2=C(OC)C(=O)C3=C(O2)C=C(O)C(OC)=C3O
Appearance
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 360.32 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: Ito Y, Kanamaru A, Tada A. Centaureidin promotes dendrite retraction of melanocytes by activating Rho. Biochim Biophys Acta. 2006 Mar;1760(3):487-94. doi: 10.1016/j.bbagen.2006.01.003. Epub 2006 Jan 27. PMID: 16476521. 2: Chang SL, Chiang YM, Chang CL, Yeh HH, Shyur LF, Kuo YH, Wu TK, Yang WC. Flavonoids, centaurein and centaureidin, from Bidens pilosa, stimulate IFN-gamma expression. J Ethnopharmacol. 2007 Jun 13;112(2):232-6. doi: 10.1016/j.jep.2007.03.001. Epub 2007 Mar 7. PMID: 17408892. 3: Orallo F, Lamela M, Camiña M, Uriarte E, Calleja JM. Preliminary study of the potential vasodilator effects on rat aorta of centaurein and centaureidin, two flavonoids from Centaurea corcubionensis. Planta Med. 1998 Mar;64(2):116-9. doi: 10.1055/s-2006-957386. PMID: 9580164. 4: Villalva M, Jaime L, Siles-Sánchez MLN, Santoyo S. Bioavailability Assessment of Yarrow Phenolic Compounds Using an In Vitro Digestion/Caco-2 Cell Model: Anti-Inflammatory Activity of Basolateral Fraction. Molecules. 2022 Nov 26;27(23):8254. doi: 10.3390/molecules27238254. PMID: 36500344; PMCID: PMC9740014. 5: El-Seedi HR, Yosri N, Khalifa SAM, Guo Z, Musharraf SG, Xiao J, Saeed A, Du M, Khatib A, Abdel-Daim MM, Efferth T, Göransson U, Verpoorte R. Exploring natural products-based cancer therapeutics derived from egyptian flora. J Ethnopharmacol. 2021 Apr 6;269:113626. doi: 10.1016/j.jep.2020.113626. Epub 2020 Nov 25. PMID: 33248183. 6: Abad MJ, Bermejo P, Alvarez M, Guerra JA, Silván AM, Villar AM. Flavonoids and a sesquiterpene lactone from Tanacetum microphyllum inhibit anti- inflammatory mediators in LPS-stimulated mouse peritoneal macrophages. Planta Med. 2004 Jan;70(1):34-8. doi: 10.1055/s-2004-815452. PMID: 14765290. 7: Shi Y, Lei Y, Guo S, Li L, Li X, Liu X, Ding S. Screening Anti-Rheumatoid Arthritis Synovitis Effective Ingredients of Total Flavonoid From Artemisia argyi Folium Based on Spectrum-Effect Relationship. Phytochem Anal. 2024 Nov 12. doi: 10.1002/pca.3479. Epub ahead of print. PMID: 39532485. 8: Long C, Sauleau P, David B, Lavaud C, Cassabois V, Ausseil F, Massiot G. Bioactive flavonoids of Tanacetum parthenium revisited. Phytochemistry. 2003 Sep;64(2):567-9. doi: 10.1016/s0031-9422(03)00208-5. PMID: 12943776. 9: Muhammad S, Maqbool MF, Al-Sehemi AG, Iqbal A, Khan M, Ullah S, Khan MT. A threefold approach including quantum chemical, molecular docking and molecular dynamic studies to explore the natural compounds from Centaurea jacea as the potential inhibitors for COVID-19. Braz J Biol. 2021 Sep 3;83:e247604. doi: 10.1590/1519-6984.247604. PMID: 34495156. 10: Forgo P, Zupkó I, Molnár J, Vasas A, Dombi G, Hohmann J. Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. Fitoterapia. 2012 Jul;83(5):921-5. doi: 10.1016/j.fitote.2012.04.006. Epub 2012 Apr 17. PMID: 22537643. 11: Stojanović G, Radulović N, Hashimoto T, Palić R. In vitro antimicrobial activity of extracts of four Achillea species: the composition of Achillea clavennae L. (Asteraceae) extract. J Ethnopharmacol. 2005 Oct 3;101(1-3):185-90. doi: 10.1016/j.jep.2005.04.026. PMID: 15978758. 12: Csupor-Löffler B, Hajdú Z, Zupkó I, Réthy B, Falkay G, Forgo P, Hohmann J. Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines. Phytother Res. 2009 May;23(5):672-6. doi: 10.1002/ptr.2697. PMID: 19107850. 13: Ahmed SA, Kamel EM. Cytotoxic activities of flavonoids from Centaurea scoparia. ScientificWorldJournal. 2014;2014:274207. doi: 10.1155/2014/274207. Epub 2014 Jun 11. PMID: 25114960; PMCID: PMC4075006. 14: Pan E, Gorka AP, Alumasa JN, Slebodnick C, Harinantenaina L, Brodie PJ, Roepe PD, Randrianaivo R, Birkinshaw C, Kingston DG. Antiplasmodial and antiproliferative pseudoguaianolides of Athroisma proteiforme from the Madagascar Dry Forest. J Nat Prod. 2011 Oct 28;74(10):2174-80. doi: 10.1021/np200499d. Epub 2011 Oct 13. PMID: 21995542; PMCID: PMC3203994. 15: Trifunović S, Vajs V, Juranić Z, Zizak Z, Tesević V, Macura S, Milosavljević S. Cytotoxic constituents of Achillea clavennae from Montenegro. Phytochemistry. 2006 May;67(9):887-93. doi: 10.1016/j.phytochem.2006.02.026. Epub 2006 Apr 17. PMID: 16616262. 16: Beutler JA, Hamel E, Vlietinck AJ, Haemers A, Rajan P, Roitman JN, Cardellina JH 2nd, Boyd MR. Structure-activity requirements for flavone cytotoxicity and binding to tubulin. J Med Chem. 1998 Jun 18;41(13):2333-8. doi: 10.1021/jm970842h. PMID: 9632366. 17: Apel L, Lorenz P, Urban S, Sauer S, Spring O, Stintzing FC, Kammerer DR. Phytochemical characterization of different yarrow species (Achillea sp.) and investigations into their antimicrobial activity. Z Naturforsch C J Biosci. 2020 Sep 7;76(1-2):55-65. doi: 10.1515/znc-2020-0149. PMID: 32897872. 18: Duan X, Li J, Cui J, Li H, Hasan B, Xin X. Chemical component and in vitro protective effects of Matricaria chamomilla (L.) against lipopolysaccharide insult. J Ethnopharmacol. 2022 Oct 5;296:115471. doi: 10.1016/j.jep.2022.115471. Epub 2022 Jun 16. PMID: 35716917. 19: Jachak SM, Gautam R, Selvam C, Madhan H, Srivastava A, Khan T. Anti- inflammatory, cyclooxygenase inhibitory and antioxidant activities of standardized extracts of Tridax procumbens L. Fitoterapia. 2011 Mar;82(2):173-7. doi: 10.1016/j.fitote.2010.08.016. Epub 2010 Sep 8. PMID: 20804828. 20: Abad MJ, Bermejo P, Villar A. The activity of flavonoids extracted from Tanacetum microphyllum DC. (Compositae) on soybean lipoxygenase and prostaglandin synthetase. Gen Pharmacol. 1995 Jul;26(4):815-9. doi: 10.1016/0306-3623(94)00242-f. PMID: 7635257.