Rose bengal (CED0002380)

Record Information

Version

1.0

Creation Date

2016-05-26 01:47:12 UTC

Update Date

2026-04-14 18:09:47 UTC

Accession Number

CHEM030278

Identification

Common Name

Rose bengal

Class

Small Molecule

Description

Rose bengal is an organic compound with the chemical formula C20H4Cl4I4O5. Rose bengal belongs to the 1-benzopyrans, a subclass of benzopyrans within the organic compounds. With an average molecular weight of 973.67 g/mol, Rose bengal is a heavy molecule. This substance is found in or released from 13 recorded sources across several categories. In the realm of healthcare, pharmaceuticals, and veterinary products, it is utilized as a diagnostic agent. It is also associated with food, food processing, and cookware, specifically in the processing of meats and the preparation of vinegar, wine, or sparkling wine, as well as cellar tools. Within the category of household cleaning and consumer products, it appears in bleaching agents, pipe accessories, cigar cigarettes, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, including antennas, video games, and electrically stimulated smoking devices. The recorded exposure route for this compound is ophthalmic.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2',4',5',7'-Tetrabromo-2,3,4,5-tetraiodofluorescein	ChEBI
3,4,5,6-tetrachloro-2',4',5',7'-Tetraiodofluorescein, 8ci	HMDB
4,5,6,7-tetrachloro-3',6'-Dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 9ci	HMDB
Ak-rose liq 1%	HMDB
C.I. 45440	HMDB
C.I. solvent red 141	HMDB
Bengal, rose	MeSH
Rose bengal	MeSH
Rose bengal sodium I 125	MeSH
Rose bengal sodium I 131	MeSH

Chemical Formula

C₂₀H₄Cl₄I₄O₅

Average Molecular Mass

973.673 g/mol

Monoisotopic Mass

971.499 g/mol

CAS Registry Number

11121-48-5

IUPAC Name

2,3,4,5-tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)benzoic acid

Traditional Name

rose bengal

SMILES

OC(=O)C1=C(C(Cl)=C(Cl)C(Cl)=C1Cl)C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C12

InChI Identifier

InChI=1S/C20H4Cl4I4O5/c21-10-8(9(20(31)32)11(22)13(24)12(10)23)7-3-1-5(25)16(29)14(27)18(3)33-19-4(7)2-6(26)17(30)15(19)28/h1-2,29H,(H,31,32)

InChI Key

VDNLFJGJEQUWRB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
2-halobenzoic acid or derivatives
3-halobenzoic acid or derivatives
4-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
2-halobenzoic acid
3-halobenzoic acid
4-halobenzoic acid
Halobenzoic acid
Benzoic acid
Benzoic acid or derivatives
Benzoyl
2-iodophenol
1-carboxy-2-haloaromatic compound
Chlorobenzene
Halobenzene
Monocyclic benzene moiety
Aryl iodide
Aryl halide
Benzenoid
Aryl chloride
Vinylogous halide
Heteroaromatic compound
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organochloride
Organoiodide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

xanthene dye (CHEBI:87202 )
organoiodine compound (CHEBI:87202 )
phenols (CHEBI:87202 )
benzoic acids (CHEBI:87202 )
tetrachlorobenzene (CHEBI:87202 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00068 g/L	ALOGPS
logP	6.02	ALOGPS
logP	9.26	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	1.81	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	176.05 m³·mol⁻¹	ChemAxon
Polarizability	63.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000000009-f3bf8c5a3e0f0a0853fc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000000009-66093dd459c6362a7d97	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-1000000009-2e8b9a120af756884330	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000000009-db1a74d9f739e534146d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-0000000009-29def3b73f15b66f7561	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-0000000019-a195e1189bd1f1119c6b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000000009-4d514593d08da0819fba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000000009-cb8d88946ddbbd8b9e9b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0000000119-bd361297dc21f404f385	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000000009-f3e6775ccbb7efabbbe2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000000009-6240466616fe0b78d3a9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0v4l-0000000019-0a9443190bf8c294261b	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
623.0	Log mg/kg	[350:1100]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
233	Brushes	Personal care & cosmetics	Not Available
402	Diagnostic agents	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
543	Cellar Tools	Food, food processing & cookware	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
549	Preparation Of Wine Or Sparkling Wine	Food, food processing & cookware	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
555	Bleaching Agents	Household cleaning & consumer products	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
581	Paper Making Machines	Industrial manufacturing & chemical processing	Not Available
603	Nematocides	Agriculture & land management	Not Available
604	Pest Attractants	Agriculture & land management	Not Available
609	Aftershave	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available
630	Toys	Recreation & sports surfaces	Not Available
631	Anthraquinone Dyes	Textiles, leather & furnishings	Not Available
633	Azo Dyes	Textiles, leather & furnishings	Not Available
638	Decorating Textiles	Textiles, leather & furnishings	Not Available
640	Embroidering And Tufting	Textiles, leather & furnishings	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
647	Multicolour Dyeing	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
657	Surface Finishing Of Leather	Textiles, leather & furnishings	Not Available
659	Transfer Printing	Textiles, leather & furnishings	Not Available
662	Yarns Or Threads	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Protein translocase subunit SecA 2	Q2FUW6	Staphylococcus aureus (strain NCTC 8325)	Predicted (SEA)	0.0778492
Click to view 3D structure	Protein translocase subunit SecA 1	O06446	Staphylococcus aureus (strain NCTC 8325)	Predicted (SEA)	0.155698
Click to view 3D structure	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1	P10686	Rattus norvegicus	Predicted (SEA)	0.622794
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	167.921
Click to view 3D structure	Flavin reductase (NADPH)	P30043	Humans	Predicted (SEA)	2.56902
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	849.335
Click to view 3D structure	Thiosulfate sulfurtransferase	Q16762	Humans	Predicted (SEA)	8.48557
Click to view 3D structure	Protein phosphatase EYA3	Q99504	Humans	Predicted (SEA)	27.0137
Click to view 3D structure	Vesicular acetylcholine transporter	Q62666	Rattus norvegicus	Predicted (SEA)	227.475
Click to view 3D structure	Translin-associated protein X	Q99598	Humans	Predicted (SEA)	13.7793
Click to view 3D structure	Tyrosine-protein kinase Lyn	Q07014	Rattus norvegicus	Predicted (SEA)	13.7793
Click to view 3D structure	Tyrosine-protein kinase Fgr	Q6P6U0	Rattus norvegicus	Predicted (SEA)	13.7793
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	3910.99
Click to view 3D structure	Deoxyribonuclease gamma	Q13609	Humans	Predicted (SEA)	40.1702
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	4749.19
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	4046.91
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	4326.47
Click to view 3D structure	G-protein coupled receptor 35	Q9HC97	Humans	Predicted (SEA)	3152.27
Click to view 3D structure	Polypeptide N-acetylgalactosaminyltransferase 2	Q10471	Humans	Predicted (SEA)	16.0369
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	4476.64
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	2747.22
Click to view 3D structure	Gag-Pol polyprotein	Q7ZJM1	Human immunodeficiency virus 1	Predicted (SEA)	1363.3
Click to view 3D structure	Heat shock 70 kDa protein 1A	P0DMV8	Humans	Predicted (SEA)	25.6124
Click to view 3D structure	Polypeptide N-acetylgalactosaminyltransferase 1	Q10472	Humans	Predicted (SEA)	31.1397
Click to view 3D structure	Polypeptide N-acetylgalactosaminyltransferase 14	Q96FL9	Humans	Predicted (SEA)	31.1397