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MedKoo Cat#: 146192 | Name: Chalepensin

Description:

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

Chalepensin is a flavonoid glycoside found in various plants, including Ruta chalepensis (common rue), and is known for its antioxidant, anti-inflammatory, and antimicrobial properties. It exerts its biological effects by scavenging free radicals and modulating inflammatory pathways, particularly by inhibiting enzymes like cyclooxygenase (COX) and lipoxygenase (LOX). Chalepensin has shown potential in treating conditions like inflammation, pain, and bacterial infections. Its therapeutic properties are being explored for use in natural medicine, particularly for managing oxidative stress-related diseases.

Chemical Structure

Chalepensin
Chalepensin
CAS#13164-03-9

Theoretical Analysis

MedKoo Cat#: 146192

Name: Chalepensin

CAS#: 13164-03-9

Chemical Formula: C16H14O3

Exact Mass: 254.0943

Molecular Weight: 254.29

Elemental Analysis: C, 75.58; H, 5.55; O, 18.88

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
Chalepensin;
IUPAC/Chemical Name
6-(2-methylbut-3-en-2-yl)-7H-furo[3,2-g]chromen-7-one
InChi Key
FYCCCUNGXGKNJV-UHFFFAOYSA-N
InChi Code
1S/C16H14O3/c1-4-16(2,3)12-8-11-7-10-5-6-18-13(10)9-14(11)19-15(12)17/h4-9H,1H2,2-3H3
SMILES Code
CC(C)(C=C)C1=CC2=C(OC1=O)C=C3OC=CC3=C2
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 254.29 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: Nahar L, Al-Majmaie S, Al-Groshi A, Rasul A, Sarker SD. Chalepin and Chalepensin: Occurrence, Biosynthesis and Therapeutic Potential. Molecules. 2021 Mar 14;26(6):1609. doi: 10.3390/molecules26061609. PMID: 33799365; PMCID: PMC7999183. 2: Ueng YF, Chen CC, Yamazaki H, Kiyotani K, Chang YP, Lo WS, Li DT, Tsai PL. Mechanism-based inhibition of CYP1A1 and CYP3A4 by the furanocoumarin chalepensin. Drug Metab Pharmacokinet. 2013;28(3):229-38. doi: 10.2133/dmpk.dmpk-12-rg-113. Epub 2012 Dec 18. PMID: 23257392. 3: Lo WS, Lim YP, Chen CC, Hsu CC, Souček P, Yun CH, Xie W, Ueng YF. A dual function of the furanocoumarin chalepensin in inhibiting Cyp2a and inducing Cyp2b in mice: the protein stabilization and receptor-mediated activation. Arch Toxicol. 2012 Dec;86(12):1927-38. doi: 10.1007/s00204-012-0902-7. Epub 2012 Jul 12. PMID: 22790670. 4: Al-Majmaie S, Nahar L, Rahman MM, Nath S, Saha P, Talukdar AD, Sharples GP, Sarker SD. Anti-MRSA Constituents from Ruta chalepensis (Rutaceae) Grown in Iraq, and In Silico Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3',7-Dimethyl ether. Molecules. 2021 Feb 19;26(4):1114. doi: 10.3390/molecules26041114. PMID: 33669881; PMCID: PMC7923287. 5: Ueng YF, Chen CC, Chung YT, Liu TY, Chang YP, Lo WS, Murayama N, Yamazaki H, Souček P, Chau GY, Chi CW, Chen RM, Li DT. Mechanism-based inhibition of cytochrome P450 (CYP)2A6 by chalepensin in recombinant systems, in human liver microsomes and in mice in vivo. Br J Pharmacol. 2011 Jul;163(6):1250-62. doi: 10.1111/j.1476-5381.2011.01341.x. PMID: 21418183; PMCID: PMC3144538. 6: Kong YC, Lau CP, Wat KH, Ng KH, But PP, Cheng KF, Waterman PG. Antifertility principle of Ruta graveolens. Planta Med. 1989 Apr;55(2):176-8. doi: 10.1055/s-2006-961917. PMID: 2748734. 7: Reisch J, Szendrei K. Photoisomerisierung des Chalepensin zum Rutolid (Clausindin) [Photoisomerization of chalepensin to rutolide (Clausindin)]. Arch Pharm (Weinheim). 1975 Dec;308(12):983-4. German. doi: 10.1002/ardp.19753081216. PMID: 1221980. 8: Heinke R, Franke K, Porzel A, Wessjohann LA, Ali NA, Schmidt J. Furanocoumarins from Dorstenia foetida. Phytochemistry. 2011 Jun;72(9):929-34. doi: 10.1016/j.phytochem.2011.03.008. Epub 2011 Apr 12. PMID: 21492886. 9: Quintanilla-Licea R, Mata-Cárdenas BD, Vargas-Villarreal J, Bazaldúa- Rodríguez AF, Kavimngeles-Hernández I, Garza-González JN, Hernández-García ME. Antiprotozoal activity against Entamoeba histolytica of plants used in northeast Mexican traditional medicine. Bioactive compounds from Lippia graveolens and Ruta chalepensis. Molecules. 2014 Dec 15;19(12):21044-65. doi: 10.3390/molecules191221044. PMID: 25517343; PMCID: PMC6271573. 10: Elizondo-Luévano JH, Rodríguez-Garza NE, Bazaldúa-Rodríguez AF, Romo-Sáenz CI, Tamez-Guerra P, Verde-Star MJ, Gomez-Flores R, Quintanilla-Licea R. Cytotoxic, Anti-Hemolytic, and Antioxidant Activities of Ruta chalepensis L. (Rutaceae) Extract, Fractions, and Isolated Compounds. Plants (Basel). 2023 Jun 2;12(11):2203. doi: 10.3390/plants12112203. PMID: 37299182; PMCID: PMC10255231. 11: Macias ML, Rojas IS, Mata R, Lotina-Hennsen B. Effect of selected coumarins on spinach chloroplast photosynthesis. J Agric Food Chem. 1999 May;47(5):2137-40. doi: 10.1021/jf981121+. PMID: 10552509. 12: El Sayed K, Al-Said MS, El-Feraly FS, Ross SA. New quinoline alkaloids from Ruta chalepensis. J Nat Prod. 2000 Jul;63(7):995-7. doi: 10.1021/np000012y. PMID: 10924184. 13: Stashenko EE, Acosta R, Martínez JR. High-resolution gas-chromatographic analysis of the secondary metabolites obtained by subcritical-fluid extraction from Colombian rue (Ruta graveolens L.). J Biochem Biophys Methods. 2000 Jul 5;43(1-3):379-90. doi: 10.1016/s0165-022x(00)00079-8. PMID: 10869689. 14: Richardson JS, Sethi G, Lee GS, Malek SN. Chalepin: isolated from Ruta angustifolia L. Pers induces mitochondrial mediated apoptosis in lung carcinoma cells. BMC Complement Altern Med. 2016 Oct 12;16(1):389. doi: 10.1186/s12906-016-1368-6. PMID: 27729078; PMCID: PMC5059921. 15: Anaya AL, Macías-Rubalcava M, Cruz-Ortega R, García-Santana C, Sánchez- Monterrubio PN, Hernández-Bautista BE, Mata R. Allelochemicals from Stauranthus perforatus, a Rutaceous tree of the Yucatan Peninsula, Mexico. Phytochemistry. 2005 Feb;66(4):487-94. doi: 10.1016/j.phytochem.2004.12.028. PMID: 15694456.

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