MedKoo Cat#: 591257 | Name: Triphenyl bismuth
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Description:

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

Triphenylbismuth (Ph₃Bi) is an organobismuth compound, which exhibits modest bioactivity, primarily in antimicrobial and enzyme inhibition assays. In vitro studies have shown that it inhibits the growth of Staphylococcus aureus and Escherichia coli with MIC values typically in the range of 64–128 µg/mL, and it shows moderate antifungal activity against Candida albicans. Its mechanism is thought to involve interference with thiol-containing enzymes or membrane-associated proteins. Additionally, it has been reported to inhibit metalloenzymes by binding to cysteine-rich active sites, and preliminary cytotoxicity screens have demonstrated IC₅₀ values in the 10–50 µM range against certain human cancer cell lines (e.g., HeLa and MCF-7), though these effects are not yet well-characterized in vivo.

Chemical Structure

Triphenyl bismuth
Triphenyl bismuth
CAS#603-33-8

Theoretical Analysis

MedKoo Cat#: 591257

Name: Triphenyl bismuth

CAS#: 603-33-8

Chemical Formula: C18H15Bi

Exact Mass: 440.0978

Molecular Weight: 440.30

Elemental Analysis: C, 49.10; H, 3.43; Bi, 47.46

Price and Availability

Size Price Availability Quantity
5g USD 450.00 2 Weeks
25g USD 950.00 2 Weeks
100g USD 1,650.00 2 Weeks
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Related CAS #
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Synonym
Triphenyl bismuth; NSC 465; NSC-465; NSC465; Triphenylbismuth;
IUPAC/Chemical Name
Bismuthine, triphenyl-
InChi Key
ZHXAZZQXWJJBHA-UHFFFAOYSA-N
InChi Code
InChI=1S/3C6H5.Bi/c3*1-2-4-6-5-3-1;/h3*1-5H;
SMILES Code
[Bi](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 440.30 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: Plokhikh AV, Falmbigl M, Golovina IS, Akbashev AR, Karateev IA, Presnyakov MY, Vasiliev AL, Spanier JE. Formation of BiFeO(3) from a Binary Oxide Superlattice Grown by Atomic Layer Deposition. Chemphyschem. 2017 Aug 5;18(15):1966-1970. doi: 10.1002/cphc.201700407. Epub 2017 Jun 20. PubMed PMID: 28631872. 2: Hiromori Y, Ido A, Aoki A, Kimura T, Nagase H, Nakanishi T. Ligand Activity of Group 15 Compounds Possessing Triphenyl Substituent for the RXR and PPARγ Nuclear Receptors. Biol Pharm Bull. 2016;39(10):1596-1603. PubMed PMID: 27725436. 3: Fernández J, Amestoy H, Sardon H, Aguirre M, Varga AL, Sarasua JR. Effect of molecular weight on the physical properties of poly(ethylene brassylate) homopolymers. J Mech Behav Biomed Mater. 2016 Dec;64:209-19. doi: 10.1016/j.jmbbm.2016.07.031. Epub 2016 Aug 2. PubMed PMID: 27517665. 4: Bučinský L, Jayatilaka D, Grabowsky S. Importance of Relativistic Effects and Electron Correlation in Structure Factors and Electron Density of Diphenyl Mercury and Triphenyl Bismuth. J Phys Chem A. 2016 Aug 25;120(33):6650-69. doi: 10.1021/acs.jpca.6b05769. Epub 2016 Aug 16. PubMed PMID: 27434184. 5: Goswami M, Ashley DC, Baik MH, Pohl NL. Mechanistic Studies of Bismuth(V)-Mediated Thioglycoside Activation Reveal Differential Reactivity of Anomers. J Org Chem. 2016 Jul 15;81(14):5949-62. doi: 10.1021/acs.joc.6b00860. Epub 2016 Jun 24. PubMed PMID: 27295299. 6: Weis F, Seipenbusch M, Kasper G. Film Growth Rates and Activation Energies for Core-Shell Nanoparticles Derived from a CVD Based Aerosol Process. Materials (Basel). 2015 Mar 6;8(3):966-976. doi: 10.3390/ma8030966. PubMed PMID: 28787982; PubMed Central PMCID: PMC5455439. 7: Islam A, Da Silva JG, Berbet FM, da Silva SM, Rodrigues BL, Beraldo H, Melo MN, Frézard F, Demicheli C. Novel triphenylantimony(V) and triphenylbismuth(V) complexes with benzoic acid derivatives: structural characterization, in vitro antileishmanial and antibacterial activities and cytotoxicity against macrophages. Molecules. 2014 May 12;19(5):6009-30. doi: 10.3390/molecules19056009. PubMed PMID: 24824136. 8: Berger RJ, Rettenwander D, Spirk S, Wolf C, Patzschke M, Ertl M, Monkowius U, Mitzel NW. Relativistic effects in triphenylbismuth and their influence on molecular structure and spectroscopic properties. Phys Chem Chem Phys. 2012 Nov 28;14(44):15520-4. doi: 10.1039/c2cp43471g. Epub 2012 Oct 17. PubMed PMID: 23072773. 9: Anjaneyulu O, Maddileti D, Kumara Swamy KC. Structural motifs in phenylbismuth heterocyclic carboxylates--secondary interactions leading to oligomers. Dalton Trans. 2012 Jan 21;41(3):1004-12. doi: 10.1039/c1dt11207d. Epub 2011 Nov 21. PubMed PMID: 22105914. 10: Xu H, Abdulghani S, Behiri J, Sabokbar A. Osteolytic potential of triphenyl bismuth as an alternative contrast medium in acrylic bone cement. J Biomed Mater Res B Appl Biomater. 2005 Oct;75(1):64-73. PubMed PMID: 16015616. 11: Abdulghani SN, Nazhat SN, Behiri JC, Deb S. Effect of triphenyl bismuth on glass transition temperature and residual monomer content of acrylic bone cements. J Biomater Sci Polym Ed. 2003;14(11):1229-42. PubMed PMID: 14768910. 12: Thurston JH, Whitmire KH. Molecular precursors for ferroelectric materials: synthesis and characterization of Bi2M2(mu-O)(sal)4(Hsal)4(OEt)2 and BiM4(mu-O)4(sal)4(Hsal)3(O(i)Pr)4 (sal = O2CC6H4O, Hsal = O2CC6H4OH) (M = Nb, Ta). Inorg Chem. 2003 Mar 24;42(6):2014-23. PubMed PMID: 12639136. 13: Arata T, Oyama Y, Tabaru K, Satoh M, Hayashi H, Ishida S, Okano Y. Cytotoxic effects of triphenylbismuth on rat thymocytes: comparisons with bismuth chloride and triphenyltin chloride. Environ Toxicol. 2002 Oct;17(5):472-7. PubMed PMID: 12242678. 14: Deb S, Abdulghani S, Behiri JC. Radiopacity in bone cements using an organo-bismuth compound. Biomaterials. 2002 Aug;23(16):3387-93. PubMed PMID: 12099281. 15: Lang LA, Mattie PA, Rawis HR. The effect of triphenylbismuth on the radiopacity and performance properties of compression- and injection-molded denture resins. J Prosthodont. 2000 Mar;9(1):23-9. PubMed PMID: 11074025. 16: Rawls HR, Granier RJ, Smid J, Cabasso I. Thermomechanical investigation of poly(methylmethacrylate) containing an organobismuth radiopacifying additive. J Biomed Mater Res. 1996 Jul;31(3):339-43. PubMed PMID: 8806059. 17: Mattie PA, Rawls HR, Cabasso I. Development of a radiopaque, autopolymerizing dental acrylic resin. J Prosthodont. 1994 Dec;3(4):213-8. PubMed PMID: 7866504. 18: Rawls HR, Marshall MV, Cardenas HL, Bhagat HR, Cabasso I. Cytotoxicity evaluation of a new radiopaque resin additive--triphenyl bismuth. Dent Mater. 1992 Jan;8(1):54-9. PubMed PMID: 1521685. 19: ADLOFF-BACHER M, ADLOFF JP. [ON THE LABELLING OF TRIPHENYL-BISMUTH BY RADIOACTIVE BISMUTH: CHROMATOGRAPHIC STUDY]. J Chromatogr. 1964 Jun;14:70-5. French. PubMed PMID: 14194377.