MedKoo Cat#: 146132 | Name: Centaurein

Description:

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

Centaurein is a natural flavonoid glycoside isolated from plants in the Centaurea genus, known for its anti-inflammatory, antioxidant, and antimicrobial properties. It has been studied for its potential therapeutic applications in managing conditions related to oxidative stress, such as cardiovascular diseases and diabetes, as well as for its ability to combat microbial infections. Centaurein exerts its effects by scavenging free radicals and inhibiting key enzymes involved in inflammatory processes, such as cyclooxygenase (COX).

Chemical Structure

Centaurein
Centaurein
CAS#35595-03-0

Theoretical Analysis

MedKoo Cat#: 146132

Name: Centaurein

CAS#: 35595-03-0

Chemical Formula: C24H26O13

Exact Mass: 522.1373

Molecular Weight: 522.46

Elemental Analysis: C, 55.17; H, 5.02; O, 39.81

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 #
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Synonym
Centaurein;
IUPAC/Chemical Name
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
InChi Key
GGMCFLXPZMBJMV-NPVWYNPDSA-N
InChi Code
1S/C24H26O13/c1-32-11-5-4-9(6-10(11)26)21-23(34-3)18(29)15-12(35-21)7-13(22(33-2)17(15)28)36-24-20(31)19(30)16(27)14(8-25)37-24/h4-7,14,16,19-20,24-28,30-31H,8H2,1-3H3/t14-,16-,19+,20-,24-/m1/s1
SMILES Code
COC1=C(O)C=C(C=C1)C2=C(OC)C(=O)C3=C(O)C(OC)=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2
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 522.46 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: 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. 2: Chang SL, Yeh HH, Lin YS, Chiang YM, Wu TK, Yang WC. The effect of centaurein on interferon-gamma expression and Listeria infection in mice. Toxicol Appl Pharmacol. 2007 Feb 15;219(1):54-61. doi: 10.1016/j.taap.2006.11.026. Epub 2006 Dec 5. PMID: 17229448. 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: Nikiema WA, Ouédraogo M, Ouédraogo WP, Fofana S, Ouédraogo BHA, Delma TE, Amadé B, Abdoulaye GM, Sawadogo AS, Ouédraogo R, Semde R. Systematic Review of Chemical Compounds with Immunomodulatory Action Isolated from African Medicinal Plants. Molecules. 2024 Apr 26;29(9):2010. doi: 10.3390/molecules29092010. PMID: 38731500; PMCID: PMC11085867. 5: Chiang YM, Chuang DY, Wang SY, Kuo YH, Tsai PW, Shyur LF. Metabolite profiling and chemopreventive bioactivity of plant extracts from Bidens pilosa. J Ethnopharmacol. 2004 Dec;95(2-3):409-19. doi: 10.1016/j.jep.2004.08.010. PMID: 15507368. 6: Kubik J, Waszak Ł, Adamczuk G, Humeniuk E, Iwan M, Adamczuk K, Michalczuk M, Korga-Plewko A, Józefczyk A. Phytochemical Analysis and Anti-Cancer Properties of Extracts of Centaurea castriferrei Borbás & Waisb Genus of Centaurea L. Molecules. 2022 Nov 3;27(21):7537. doi: 10.3390/molecules27217537. PMID: 36364358; PMCID: PMC9658107. 7: Maldonado-Rojas W, Olivero-Verbel J, Marrero-Ponce Y. Computational fishing of new DNA methyltransferase inhibitors from natural products. J Mol Graph Model. 2015 Jul;60:43-54. doi: 10.1016/j.jmgm.2015.04.010. Epub 2015 Jun 3. PMID: 26099696. 8: Ahmad M, Muhammad N, Mehjabeen, Jahan N, Ahmad M, Obaidullah, Qureshi M, Jan SU. Spasmolytic effects of Scrophularia nodosa extract on isolated rabbit intestine. Pak J Pharm Sci. 2012 Jan;25(1):267-75. PMID: 22186340.