A xanthene dye, fluorescein derivative, and photosensitizer
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Rose Bengal (sodium salt)

Item No. 28829

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,5,6,7-tetrachloro-3′,6′-dihydroxy-2′,4′,5′,7′-tetraiodo-spiro[isobenzofuran-1(3H),9′-[9H]xanthen]-3-one, disodium salt
CAS Number
632-69-9
Synonyms
  • Acid Red 94
  • Japan Red 105-1
  • Red No. 105-1
Molecular Formula
C20H2Cl4I4O5 • 2Na
Formula Weight
1017.6
Emission
567 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly SolubleDMSO: 10 mg/mlEthanol: Slightly SolublePBS (pH 7.2): Slightly Soluble
λmax
219, 558 nm
SMILES
IC1=CC2=C(C(I)=C1[O-])OC3=C(I)C([O-])=C(I)C=C3C24C(C(Cl)=C(Cl)C(Cl)=C5Cl)=C5C(O4)=O.[Na+].[Na+]
InChi Code
InChI=1S/C20H4Cl4I4O5.2Na/c21-9-7-8(10(22)12(24)11(9)23)20(33-19(7)31)3-1-5(25)15(29)13(27)17(3)32-18-4(20)2-6(26)16(30)14(18)28;;/h1-2,29-30H;;/q;2*+1/p-2
InChi Key
KCQREHTWEUECQT-UHFFFAOYSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 g

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    Product Description

    Rose bengal is a xanthene dye, fluorescein derivative, and photosensitizer.1,2 It exhibits absorption/emission maxima of 548/567 nm, respectively.3 Rose bengal binds to S. aureus cells and decreases survival of photoirradiated S. aureus to 0.012% when used at a concentration of 1 μM.1 It generates singlet oxygen when exposed to photoirradiation in cell-free assays and induces potassium ion leakage from S. aureus and bovine erythrocytes in the presence of photoirradiation. Rose bengal inhibits the cytochrome P450 (CYP) isoform CYP3A4/5 and the UDP-glucuronosyltransferase (UGT) isoform UGT1A6 in human liver microsomes in a light-dependent manner, with IC50 values of 0.072 and 0.035 μM, respectively, in yellow light, 3.1 and 4.2 μM, respectively, in ambient light, and 3 and 4.2 μM, respectively, in the dark.4 It has been used for staining of live cells, but exhibits both intrinsic and phototoxicity.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kato, H., Komagoe, K., Nakanishi, Y., et al. Xanthene dyes induce membrane permeabilization of bacteria and erythrocytes by photoinactivation. Photochem. Photobiol. 88(2), 423-431 (2012).

    2. Feenstra, R.P.G., and Tseng, S.C.G. Comparison of fluorescein and rose bengal staining. Ophthalmology 99(4), 605-617 (1992).

    3. Sabnis, R.W. Handbook of biological dyes and stains: Synthesis and industrial applications. (2010).

    4. Kazmi, F., Haupt, L.J., Horkman, J.R., et al. In vitro inhibition of human liver cytochrome P450 (CYP) and UDP-glucuronosyltransferase (UGT) enzymes by rose bengal: System-dependent effects on inhibitory potential. Xenobiotica 44(7), 606-614 (2014).