Bromophene

Bromophene (MC21-A or C58) is a bactericidal antibiotic first isolated from the O-BC30 strain of a marine bacterium, Pseudoalteromonas phenolica.^[1] A 2024 study reported that bromophene exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), with a minimum inhibitory concentration of 2 μg/mL against 39 different isolates. In the same study, bromophene exhibited in vitro antibacterial activity comparable to or greater than that of daptomycin, vancomycin, and linezolid under the conditions tested.^[2] Additionally, bromophene eradicated established MRSA biofilms at a concentration of 8 μg/mL in vitro, whereas vancomycin did not achieve partial biofilm eradication at the concentrations evaluated in the same study.^[2]

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Bromophene

Names
Preferred IUPAC name 3,3′,5,5′-Tetrabromo[1,1′-biphenyl]-2,2′-diol
Other names MC21-A; C58; 2,2'-Dihydroxy-3,3',5,5'-tetrabromobiphenyl; 3,3',5,5'-Tetrabromo-2,2'-biphenyldiol
Identifiers
CAS Number	21987-62-2
3D model (JSmol)	Interactive image
ChemSpider	28660
ECHA InfoCard	100.161.669
MeSH	3,3',5,5'-tetrabromo-2,2'-biphenyldiol
PubChem CID	30891
RTECS number	DV5185000
UNII	3BG8N9724B Y
CompTox Dashboard (EPA)	DTXSID30176404
InChI InChI=1S/C12H6Br4O2/c13-5-1-7(11(17)9(15)3-5)8-2-6(14)4-10(16)12(8)18/h1-4,17-18H Key: TXODBIOSWNNKJM-UHFFFAOYSA-N
SMILES C1=C(C=C(C(=C1Br)O)C2=CC(=CC(=C2O)Br)Br)Br
Properties
Chemical formula	C12H6Br4O2
Molar mass	501.794 g·mol−1
Appearance	White, needle-like crystals or white powder. (Crystallization from acetone, EtOH or CHCl3)
Melting point	205 to 207 °C (401 to 405 °F; 478 to 480 K)
Solubility in water	Sol. DMSO, Acetone, CHCl3 Slightly Sol. EtOH, MeOH Insol. H2O, hexane
Related compounds
Related biphenyls	MC21-B Polybrominated biphenyl
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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