MedKoo Cat#: 461567 | Name: Rutamarin

Description:

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

Rutamarin is a cytotoxic compound that is an agonist of TRPM5 and TRPV1 and a strong antagonist of TRPM8 ion channels.

Chemical Structure

Rutamarin
Rutamarin
CAS#14882-94-1

Theoretical Analysis

MedKoo Cat#: 461567

Name: Rutamarin

CAS#: 14882-94-1

Chemical Formula: C21H24O5

Exact Mass: 356.1624

Molecular Weight: 356.41

Elemental Analysis: C, 70.77; H, 6.79; O, 22.44

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
Rutamarin;
IUPAC/Chemical Name
2-(6-(2-methylbut-3-en-2-yl)-7-oxo-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl acetate
InChi Key
AWMHMGFGCLBSAY-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H24O5/c1-7-20(3,4)15-9-13-8-14-10-18(21(5,6)26-12(2)22)24-16(14)11-17(13)25-19(15)23/h7-9,11,18H,1,10H2,2-6H3
SMILES Code
O=C1C(C(C)(C)C=C)=CC2=CC3=C(OC(C(C)(OC(C)=O)C)C3)C=C2O1
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 356.41 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: Xu B, Wang L, González-Molleda L, Wang Y, Xu J, Yuan Y. Antiviral activity of (+)-rutamarin against Kaposi's sarcoma-associated herpesvirus by inhibition of the catalytic activity of human topoisomerase II. Antimicrob Agents Chemother. 2014;58(1):563-73. doi: 10.1128/AAC.01259-13. Epub 2013 Dec 2. PubMed PMID: 24295975; PubMed Central PMCID: PMC3910736. 2: Zhang Y, Zhang H, Yao XG, Shen H, Chen J, Li C, Chen L, Zheng M, Ye J, Hu L, Shen X, Jiang H. (+)-Rutamarin as a dual inducer of both GLUT4 translocation and expression efficiently ameliorates glucose homeostasis in insulin-resistant mice. PLoS One. 2012;7(2):e31811. doi: 10.1371/journal.pone.0031811. Epub 2012 Feb 27. PubMed PMID: 22384078; PubMed Central PMCID: PMC3288053. 3: Wu T, Wang Y, Yuan Y. Antiviral activity of topoisomerase II catalytic inhibitors against Epstein-Barr virus. Antiviral Res. 2014 Jul;107:95-101. doi: 10.1016/j.antiviral.2014.05.003. Epub 2014 May 10. PubMed PMID: 24821256. 4: Mancuso G, Borgonovo G, Scaglioni L, Bassoli A. Phytochemicals from Ruta graveolens Activate TAS2R Bitter Taste Receptors and TRP Channels Involved in Gustation and Nociception. Molecules. 2015 Oct 16;20(10):18907-22. doi: 10.3390/molecules201018907. PubMed PMID: 26501253. 5: Minker E, Bartha C, Rózsa Z, Szendrei K, Reisch J. Antispasmogenic effect of rutamarin and arborinine on isolated smooth muscle organs. Planta Med. 1979 Oct;37(2):156-60. PubMed PMID: 515224. 6: Reisch J, Novàk I, Szendrei K, Minker E. [Rutamarin, coumarin derivative of Ruta graveolens]. Acta Pharm Suec. 1967 Apr;4(2):179-81. German. PubMed PMID: 6041055. 7: Yang QY, Tian XY, Fang WS. Bioactive coumarins from Boenninghausenia sessilicarpa. J Asian Nat Prod Res. 2007 Jan-Feb;9(1):59-65. PubMed PMID: 17365191. 8: 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. PubMed PMID: 27729078; PubMed Central PMCID: PMC5059921. 9: Rollinger JM, Schuster D, Danzl B, Schwaiger S, Markt P, Schmidtke M, Gertsch J, Raduner S, Wolber G, Langer T, Stuppner H. In silico target fishing for rationalized ligand discovery exemplified on constituents of Ruta graveolens. Planta Med. 2009 Feb;75(3):195-204. doi: 10.1055/s-0028-1088397. Epub 2008 Dec 18. Erratum in: Planta Med. 2009 Feb;75(3):293. PubMed PMID: 19096995; PubMed Central PMCID: PMC3525952. 10: Suhaimi SA, Hong SL, Abdul Malek SN. Rutamarin, an Active Constituent from Ruta angustifolia Pers., Induced Apoptotic Cell Death in the HT29 Colon Adenocarcinoma Cell Line. Pharmacogn Mag. 2017 Jul;13(Suppl 2):S179-S188. doi: 10.4103/pm.pm_432_16. Epub 2017 Jul 11. PubMed PMID: 28808378; PubMed Central PMCID: PMC5538152. 11: Orlita A, Sidwa-Gorycka M, Kumirska J, Maliński E, Siedlecka EM, Gajdus J, Lojkowska E, Stepnowski P. Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors. Biotechnol Prog. 2008 Jan-Feb;24(1):128-33. Epub 2007 Dec 6. PubMed PMID: 18052337. 12: Lin Y, Wang Q, Gu Q, Zhang H, Jiang C, Hu J, Wang Y, Yan Y, Xu J. Semisynthesis of (-)-Rutamarin Derivatives and Their Inhibitory Activity on Epstein-Barr Virus Lytic Replication. J Nat Prod. 2017 Jan 27;80(1):53-60. doi: 10.1021/acs.jnatprod.6b00415. Epub 2017 Jan 17. PubMed PMID: 28093914. 13: Chen YS. [Studies on lactone constituents from Boennighausenia sessilicarpa Lévl]. Yao Xue Xue Bao. 1989;24(4):260-3. Chinese. PubMed PMID: 2816386. 14: Orlita A, Sidwa-Gorycka M, Paszkiewicz M, Malinski E, Kumirska J, Siedlecka EM, Łojkowska E, Stepnowski P. Application of chitin and chitosan as elicitors of coumarins and fluoroquinolone alkaloids in Ruta graveolens L. (common rue). Biotechnol Appl Biochem. 2008 Oct;51(Pt 2):91-6. doi: 10.1042/BA20070200. PubMed PMID: 18211259. 15: Orlita A, Sidwa-Gorycka M, Malinski E, Czerwicka M, Kumirska J, Golebiowski M, Lojkowska E, Stepnowski P. Effective biotic elicitation of Ruta graveolens L. shoot cultures by lysates from Pectobacterium atrosepticum and Bacillus sp. Biotechnol Lett. 2008 Mar;30(3):541-5. Epub 2007 Oct 30. PubMed PMID: 17968510.