Basic information
- CAS
152-74-9- Standard SMILES
O=C(O)c1c(Cl)c(Cl)c(Cl)c(Cl)c1-c1c2cc(I)c(=O)c(I)c-2oc2c(I)c(O)c(I)cc12- InChIKey
VDNLFJGJEQUWRB-UHFFFAOYSA-N- Molecular formula
- C20H4Cl4I4O5
- Average molar mass
- 973.7 g/mol
- Monoisotopic mass
- 971.4992
Overview
Rose bengal free acid is a xanthene dye that is fluorescein bearing bromine substituents at positions 2', 4', 5' and 7' (on the xanthene ring) and iodine substituents at position 2, 3, 4, and 5 (on the phenyl ring). The dipotassium salt is the biological stain 'rose bengal'. It has a role as a fluorochrome. It is a member of benzoic acids, a tetrachlorobenzene, a member of phenols, an organoiodine compound and a xanthene dye. It is functionally related to a fluorescin. It is a conjugate acid of a rose bengal(2-).
Names & identifiers
- Preferred name
- 2,3,4,5-Tetrachloro-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxo-xanthen-9-yl)benzoic acid
- IUPAC
- 2,3,4,5-tetrachloro-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxoxanthen-9-yl)benzoic acid
- English name
- Spiro(isobenzofuran-1(3H),9'(9H)-xanthen)-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-
- Molecular formula
- C20H4Cl4I4O5
- Molecular weight
- 973.67264
Names & synonyms
rose-bengalrose bengal free acid2,3,4,5-Tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)benzoic acid152-74-9CHEBI:872022,3,4,5-tetrachloro-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxo-xanthen-9-yl)benzoic acidNSC10463NSC45732NSC-10463NSC270091BengalrosaRose bengale (base)
Show more names
4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro(isobenzofuran-1(3H),9'(9H)-xanthen)-3-oneSpiro(isobenzofuran-1(3H),9'(9H)-xanthen)-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-
Ak-Rose Liq 1%TetraiodotetrachlorofluoresceinGTPL2393SCHEMBL1464825CHEMBL1208422SCHEMBL29352253DTXSID20859517BDBM50541116
Database identifiers
- CAS
152-74-9、4159-77-7、632-69-9- PubChem CID
- 25474
- DTXSID
DTXSID20859517- ChEMBL
CHEMBL1208422- ChEBI
CHEBI:87202- Nikkaji
- J84.910C
Properties
Computed structural properties
- XLogP
- 7.6
- Topological polar surface area
- 83.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 988
Experimental & physicochemical properties
Melting PointDecomposes
Physicochemical properties
- FDA UNII
- 7 Q7W2SH · BIU7Q7W2SH
Chemistry & industry
Pharmacology
Protein Binding
Tear component comprising of different proteins, such as albumin (although not very common as tear component), lactoferrin, and transferrin, can bind to rose bengal dye and act as diffusion barrier to prevent dye uptake by cells and subsequent cell staining. Lysosymes in tear film can also bind to rose bengal to form precipitates to attenuate cell uptake.
Pharmacodynamics
Rose bengal is a staining agent that visualized ocular surfaces of both diseased and dead cells _in vivo_. It has also shown to stain healthy cultured cells, including rabbit corneal epithelial cells, in a rapid, dose-dependent manner. Various studies demonstrate the cytotoxic effects of rose bengal in different cell cultures, including smooth-muscle cells from human intestine, endothelial cells from bovinepulmonary artery, rabbit Tenon fibro-blasts, and rabbit and human corneal epithelial cells. Cellular morphological changes such as detachment, separation, loss of motility and disruption, in addition to swelling, intracytoplasmic vacuole formation and lysis have been manifested with the treatment of rose bengal, indicating that rose Bengal is not a vital dye.
Mechanism of Action
Rose Bengal stains both the nuclei and cell walls of dead or degenerated epithelial cells of the cornea and conjunctiva, and stain the mucus of the precorneal tear film. It is proposed that the staining ability of rose bengal is dependent on the status of tear film protection rather than cell viability, as tear components such as albumin and mucin can block the rose bengal uptake. It induces intrinsic cytotoxic effects by causing cellular morphologic changes, subsequent loss of cellular motility, cell detachment, and cell death. It mediates inhibitory actions on bovine corneal endothelial cells and attenuates cell proliferation.
Biological Half-LifeDoses between 0.01 and 10 mg/kg in rat resulted in an initial biological half-life of 2 min and a terminal half-life of 100 min. The biological half-life for excretion is around 30 minutes in rats and rabbits.
Metabolism/MetabolitesNo information available.
Absorption, Distribution and Excretion
No information available.
Rose bengal undergoes biliary excretion.
No information available.
No information available.
Cellular LocationsMembrane
Suppliers1 total
安徽今昱生物化工产品技术研发有限公司055167162561 13295518198 · [email protected]
Additional notes
DefinitionChEBI: Rose bengal free acid is a xanthene dye that is fluorescein bearing bromine substituents at positions 2', 4', 5' and 7' (on the xanthene ring) and iodine substituents at position 2, 3, 4, and 5 (on the phenyl ring). The dipotassium salt is the biological stain 'rose bengal'. It has a role as a fluorochrome. It is a member of benzoic acids, a tetrachlorobenzene, a xanthene dye, a member of phenols and an organoiodine compound. It is functionally related to a fluorescin. It is a conjugate acid of a rose bengal(2-).
Related reactions
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Compound notes
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