Rose Bengal Lactone
Solvent Red 141 · Rose bengal lactone · 4’,5’,7’-tetraiodo-droxy-2 · C.I.Solvent Red 141:C.I.45440:1 · 4,5,6,7-Tetrachloro-2’,4’,5’,7’-tetraiodofluorescein · spiro[isobenzofuran-1(3h),9’-[9h]xanthen]-3-one,4,5,6,7-tetrachloro-3’,6’-dihy · 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one · 4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
Identifiers & Physical Properties
| CAS No. | 4159-77-7 |
|---|---|
| Molecular formula | C20H4Cl4I4O5 |
| Average molar mass | 973.7 g/mol |
| Monoisotopic mass | 971.4992 g/mol |
| SMILES | O=C1OC2(c3cc(I)c(O)c(I)c3Oc3c2cc(I)c(O)c3I)c2c(Cl)c(Cl)c(Cl)c(Cl)c21 |
| InChIKey | IICCLYANAQEHCI-UHFFFAOYSA-N |
| PubChem CID | 69439 |
| EC No. | 211-182-8 |
| DTXSID | DTXSID0048426 |
Chemical & Physical Properties
| XLogP | 8.5 |
|---|---|
| Topological polar surface area | 76 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 0 |
| Heavy atoms | 33 |
| Formal charge | 0 |
| Complexity | 780 |
| Melting point | 280 °C (dec.)(lit.) |
| Storage conditions | room temp |
| Boiling point | 741.8±60.0 °C(Predicted) |
| Density | 2.96±0.1 g/cm3(Predicted) |
| pKa (acidity coefficient) | 7.03±0.20(Predicted) |
| Physical state | powder |
| Color | pink to red |
| λmax | 557 nm |
| ε(extinction coefficient) | ≥10000 at 317-323nm≥30000 at 516-522nm≥95000 at 554-560nm |
| Major applications | diagnostic assay manufacturinghematologyhistology |
| InChI | 1S/C20H4Cl4I4O5/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 |
| InChIKey | IICCLYANAQEHCI-UHFFFAOYSA-N |
| SMILES | Oc1c(I)cc2c(Oc3c(I)c(O)c(I)cc3C24OC(=O)c5c(Cl)c(Cl)c(Cl)c(Cl)c45)c1I |
| FDA UNII | BIU7Q7W2SH |
| EPA Substance Registry System | Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo- (4159-77-7) |
| UNSPSC Code | 12171500 |
| NACRES | NA.47 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-37/39 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Safety & Regulations
| GHS classification | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.This chemical does not meet GHS hazard criteria for 100% (5 of 5) of all reports. |
|---|---|
| Regulatory information | Chemical: Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-, dipotassium saltSpiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-, dipotassium salt: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (100%)Not Classified |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
Applications & Uses
Description
Rose bengal lactone is a potent inhibitor of human metabolism that binds to the proteasome pathway and inhibits the polymerization of tubulin. It has been shown to bind with high affinity to microtubules and inhibit their assembly, which leads to cell death. Rose bengal lactone also binds with high affinity to potassium ion, which may contribute to its anti-cancer effects. This compound has also been found to be an effective inhibitor of goiters in rats by binding with aliphatic hydrocarbons such as cholesterol.
Uses
Biological stain; colorant for inks, cellulosics, foods, cosmetics, medicine (diagnostic aid).
Preparation & Synthesis
Preparation
will Resorcinol and 4,5,6,7-Tetrachloroisobenzofuran-1,3-dione condensation, The resulting 4,5,6,7 – tetrachloro-fluorescein tetraiodide.