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MedKoo Cat#: 145917 | Name: Thiocoumarin

Description:

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

Thiocoumarin is a sulfur-containing derivative of coumarin, a compound known for its potential biological activities. It has been studied for its antimicrobial, antioxidant, and anticancer properties. The mechanism of thiocoumarin involves the inhibition of enzymes and the disruption of cellular processes that are essential for the survival and proliferation of harmful cells, such as cancerous or microbial cells. Due to its ability to modulate these biological pathways, thiocoumarin is being explored for its therapeutic potential in treating infections and cancer, as well as in developing antioxidant treatments.

Chemical Structure

Thiocoumarin
Thiocoumarin
CAS#3986-98-9

Theoretical Analysis

MedKoo Cat#: 145917

Name: Thiocoumarin

CAS#: 3986-98-9

Chemical Formula: C14H17NO2S

Exact Mass: 263.1000

Molecular Weight: 263.36

Elemental Analysis: C, 63.85; H, 6.51; N, 5.32; O, 12.15; S, 12.17

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
Thiocoumarin;
IUPAC/Chemical Name
4-(3-(dimethylamino)propoxy)-2H-thiochromen-2-one
InChi Key
DIOZFKOOIBATNZ-UHFFFAOYSA-N
InChi Code
1S/C14H17NO2S/c1-15(2)8-5-9-17-12-10-14(16)18-13-7-4-3-6-11(12)13/h3-4,6-7,10H,5,8-9H2,1-2H3
SMILES Code
CN(C)CCCOC1=CC(=O)SC2=CC=CC=C12
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 263.36 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: Ma J, Ripp A, Wassy D, Dürr T, Qiu D, Häner M, Haas T, Popp C, Bezold D, Richert S, Esser B, Jessen HJ. Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties. Molecules. 2020 Nov 15;25(22):5325. doi: 10.3390/molecules25225325. PMID: 33203096; PMCID: PMC7696096. 2: Agrelo-Lestón A, Llorca J, Martínez E, Angurell I, Rodríguez L, Soler L. Thiocoumarin-based Au(I) Complexes and Au(0) Systems over TiO2 as Hybrid Photocatalysts for Hydrogen Generation under UV-Vis Light. Adv Sci (Weinh). 2024 Dec;11(47):e2404969. doi: 10.1002/advs.202404969. Epub 2024 Nov 5. PMID: 39498827; PMCID: PMC11653606. 3: Rohilla S, Shah S, Singh VK. Copper-Catalyzed Asymmetric Propargylic [3 + 2] Cycloaddition: Synthesis of Enantioenriched Dihydrofuro[3,2-c]coumarins and its Quinolinone and Thiocoumarin Analogues. Org Lett. 2023 May 26;25(20):3733-3738. doi: 10.1021/acs.orglett.3c01198. Epub 2023 May 16. PMID: 37192010. 4: Cho M, Nguyen VN, Yoon J. Simultaneous Detection of Hypochlorite and Singlet Oxygen by a Thiocoumarin-Based Ratiometric Fluorescent Probe. ACS Meas Sci Au. 2022 Jan 28;2(3):219-223. doi: 10.1021/acsmeasuresciau.1c00055. PMID: 36785865; PMCID: PMC9838813. 5: Carta F. Non-sulfonamide bacterial CA inhibitors. Enzymes. 2024;55:193-212. doi: 10.1016/bs.enz.2024.06.007. Epub 2024 Jul 20. PMID: 39222991. 6: Park JE, Choi MG, Chang SK. Colorimetric and fluorescent signaling of Au3+ by desulfurization of thiocoumarin. Inorg Chem. 2012 Mar 5;51(5):2880-4. doi: 10.1021/ic202080v. Epub 2012 Feb 10. PMID: 22324661. 7: Jung JC, Kim JC, Park OS, Jang BS. Synthesis of 4-hydroxy-1-thiocoumarin derivatives-1: an efficient synthesis of thioflocoumafen. Arch Pharm Res. 1999 Jun;22(3):302-5. doi: 10.1007/BF02976367. PMID: 10403135. 8: Shinde RG, Khan AA, Barik A. Formation of two centre three electron bond by hydroxyl radical induced reaction of thiocoumarin: evidence from experimental and theoretical studies. Free Radic Res. 2019 Jun;53(6):629-640. doi: 10.1080/10715762.2019.1617417. Epub 2019 May 27. PMID: 31072168. 9: Nandi GC, Samai S, Singh MS. Biginelli and Hantzsch-type reactions leading to highly functionalized dihydropyrimidinone, thiocoumarin, and pyridopyrimidinone frameworks via ring annulation with β-oxodithioesters. J Org Chem. 2010 Nov 19;75(22):7785-95. doi: 10.1021/jo101572c. Epub 2010 Oct 27. PMID: 20979420. 10: El-Khatib RM, Nassr LA. Reactivity trends of the base hydrolysis of coumarin and thiocoumarin in binary aqueous-methanol mixtures at different temperatures. Spectrochim Acta A Mol Biomol Spectrosc. 2007 Jul;67(3-4):643-8. doi: 10.1016/j.saa.2006.08.023. Epub 2006 Aug 24. PMID: 17023196. 11: Matos MJ, Santana L, Uriarte E, Borges F. Thiocoumarins: From the Synthesis to the Biological Applications. Molecules. 2022 Jul 31;27(15):4901. doi: 10.3390/molecules27154901. PMID: 35956851; PMCID: PMC9369797. 12: Debnath M , Sasmal S , Haldar D . Fabrication of egg shell-like nanovesicles from a thiocoumarin-based ε-amino ester: a potential carrier. J Mater Chem B. 2017 Jul 21;5(27):5450-5457. doi: 10.1039/c7tb00025a. Epub 2017 Jun 29. PMID: 32264084. 13: Tanaka K. Supramolecular photodimerization of coumarins. Molecules. 2012 Feb 3;17(2):1408-18. doi: 10.3390/molecules17021408. PMID: 22306830; PMCID: PMC6268627. 14: Smith DG, Mitchell L, New EJ. Pattern recognition of toxic metal ions using a single-probe thiocoumarin array. Analyst. 2018 Dec 17;144(1):230-236. doi: 10.1039/c8an01747f. PMID: 30480672. 15: Egodawaththa NM, Rajhel O, Ma J, Guruge C, Pabarue AB, Harris E, Peverati R, Nesnas N. Highly efficient Ca2+ chelation activated by visible light. Org Biomol Chem. 2024 Sep 11;22(35):7194-7202. doi: 10.1039/d4ob00951g. PMID: 39161284; PMCID: PMC11717440. 16: Ma J, Egodawaththa NM, Guruge C, Márquez OAV, Likes M, Nesnas N. Blue and Green Light Responsive Caged Glutamate. J Photochem Photobiol A Chem. 2024 Jan 15;447:115183. doi: 10.1016/j.jphotochem.2023.115183. Epub 2023 Sep 18. PMID: 37928883; PMCID: PMC10621743. 17: Tanaka K, Toda F, Mochizuki E, Yasui N, Kai Y, Miyahara I I, Hirotsu K. Enantioselective Single-Crystal-to-Single-Crystal Photodimerization of Coumarin and Thiocoumarin in Inclusion Complexes with Chiral Host Compounds. Angew Chem Int Ed Engl. 1999 Dec 3;38(23):3523-3525. doi: 10.1002/(sici)1521-3773(19991203)38:23<3523::aid-anie3523>3.3.co;2-7. PMID: 10602229. 18: Eiden F, Zimmermann E. Uber die Reaktion von 4-Hydroxycumarin, 4-Hydroxy-1-thiocumarin und 4-Mercaptocumarin mit Diphenylketen [The reaction of 4-hydroxycoumarin, 4-hydroxy-1-thiocoumarin and 4-mercaptocoumarin with diphenylketene (author's transl)]. Arch Pharm (Weinheim). 1976 Aug;309(8):619-24. German. doi: 10.1002/ardp.19763090803. PMID: 971050. 19: DE POI LP, PITZURRA M, NEGRI M. [Antibacterial properties of thiocoumarin and its 7-substituted derivatives]. Boll Chim Farm. 1962 May;101:376-9. Italian. PMID: 13884474. 20: Supuran CT. Carbonic anhydrase inhibition/activation: trip of a scientist around the world in the search of novel chemotypes and drug targets. Curr Pharm Des. 2010;16(29):3233-45. doi: 10.2174/138161210793429797. PMID: 20819070.