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C.I. Acid Blue 90

HCID 61363
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
6104-58-1
Standard SMILES
CCOc1ccc(Nc2ccc(C(=C3C=CC(=[N+](CC)Cc4cccc(S(=O)(=O)[O-])c4)C=C3C)c3ccc(N(CC)Cc4cccc(S(=O)(=O)[O-])c4)cc3C)cc2)cc1.[Na+]
InChIKey
RWVGQQGBQSJDQV-UHFFFAOYSA-M
Molecular formula
C47H48N3NaO7S2
Average molar mass
854 g/mol
Monoisotopic mass
853.28313751

Overview

Brilliant Blue G is used in an ophthalmic solution for staining the internal limiting membrane (ILM) of the eye during ophthalmic procedures. This membrane is thin and translucent, making it difficult to identify during eye surgeries that require high levels of visual accuracy. Brilliant blue G, like its name, imparts a vibrant blue color, facilitating identification of the ILM. It was approved by the FDA for ophthalmic use on December 20, 2019.

Names & identifiers

Preferred name
C.I. Acid Blue 90
IUPAC
sodium 3-[[4-[[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-N-ethyl-3-methylanilino]methyl]benzenesulfonate
English name
Acid Blue 90
Molecular formula
C47H48N3NaO7S2
Molecular weight
854.02

Names & synonyms

Brilliant Blue G6104-58-1Acid Blue 90C.I. Acid Blue 90Derma Cyanine GImpero Azure GBenzyl Cyanine GBrilliant Blue JOptanol Cyanine GCoomassie Blue G 250Fenazo Blue XXFGAcidine Sky Blue G
Show more names
BRILLIANT BLUECOOMASSIE BRILLIANT BLUE G-250G-250CI 42655CBB G-250Cyanine GBlue G 250CI NO 42655
Silk Fast Cyanine GWater Blue 150tissueblueBrilliant Acid Blue GBrilliant Acid Blue JBrilliant Acid Blue GICoomassie Brilliant Blue GAcid Brilliant Cyanine G

Database identifiers

CAS
6104-58-1
PubChem CID
61363
ChEMBL
CHEMBL4173394
UNII
M1ZRX790SI
EC Number
228-058-4

Properties

Computed structural properties

Topological polar surface area
159 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
9
Rotatable bonds
13
Heavy atoms
60
Formal charge
0
Complexity
1,610

Experimental & physicochemical properties

Chemical ClassesDyes -> Di- and Triaryl Dyes
Solubility1mg/mL
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionBlue crystals; [MSDSonline]

Physicochemical properties

Melting point
100 °C · 100 °C
Density
1.274 · 1.274[at 20℃]
bulk density
520 kg/m3 · 520kg/m3
vapor pressure
0.093 Pa · 0.093Pa at 20℃
Flash point
11 °C · 11 °C
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: soluble1mg/mL
form
Solid
Colour Index
42655 · 42655
color

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

This chemical does not meet GHS hazard criteria for 49.3% (101 of 205) of reports.

H411 (50.7%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 205 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: Benzenemethanaminium, N-[4-[[4-[(4-ethoxyphenyl)amino]phenyl][4-[ethyl[(3-sulfophenyl)methyl]amino]-2-methylphenyl]methylene]-3-methyl-2,5-cyclohexadien-1-ylidene]-N-ethyl-3-sulfo-, hydroxide, inner salt, monosodium salt

REACH registered substance: Hydrogen [4-[4-(p-ethoxyanilino)-4'-[ethyl(m-sulphonatobenzyl)amino]-2'-methylbenzhydrylene]-3-methylcyclohexa-2,5-dien-1-ylidene](ethyl)(m-sulphonatobenzyl)ammonium, monosodium salt (EC: 228-058-4)

Benzenemethanaminium, N-4-4-(4-ethoxyphenyl)aminophenyl4-ethyl(3-sulfophenyl)methylamino-2-methylphenylmethylene-3-methyl-2,5-cyclohexadien-1-ylidene-N-ethyl-3-sulfo-, inner salt, monosodium salt: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin, eye, and respiratory tract irritant; [MSDSonline]
Hazard Classes and CategoriesAquatic Chronic 2 (50.7%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Brilliant blue g

vNo-DILI-concern

0

No match

Chemistry & industry

Pharmacology

PharmacodynamicsBrilliant Blue G aids in ophthalmologic surgery by rendering it easier to identify the internal limiting membrane (ILM) for surgical removal.
Mechanism of Action · 1 item

The internal limiting membrane (ILM) is a thin and translucent structure that demarcates the transition from the retina from the vitreous body of the eye. It acts as a scaffold on which excessive tissue can grow, which results in visual distortion when it is projected onto the neighbouring retina. This causes visual loss and/or distortion. An epiretinal membrane (also known as ERM) is a fibrous type of tissue that can be found on the inner surface of the retina and occurs idiopathically, and in some cases, retinal detachment and inflammation. It is often found on the surface of the internal limiting membrane (ILM), causing visual loss and distortion. The above condition as well as the associated macular pucker or traction maculopathy can affect the ILM, contributing to visual complications. The removal of the ILM with or without vitrectomy is often a simple solution to these conditions. Brilliant Blue G specifically stains the internal limiting membrane (ILM) in the eye without staining the epiretinal membrane or the retina, allowing for easier surgical removal. The mechanism of its specific staining that is limited to the ILM is currently not fully understood.

FDA Pharmacological Classification · 6 items

M1ZRX790SI

BRILLIANT BLUE G

Established Pharmacologic Class [EPC] - Disclosing Agent

Mechanisms of Action [MoA] - Dyes

Brilliant blue g is a Disclosing Agent. The mechanism of action of brilliant blue g is as a Dye.

BRILLIANT BLUE G

MeSH Pharmacological Classification · 1 item

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Dark blue-violet-brown
PH
6.4 · 6.4 (20°C, 10g/L in H2O)
Water Solubility
Soluble in water (50 mg/ml) and ethanol (40 mg/ml).
BRN
5230822 · 5230822
Stability
Light Sensitive
InChIKey
JFNOCRSXNFZMNT-UHFFFAOYSA-M
SMILES
[Na+].[S](=O)(=O)([O-])c1cc(ccc1)CN(CC)c2cc(c(cc2)[C+](c5c(cc(cc5)N(CC)Cc6cc(ccc6)[S](=O)(=O)[O-])C)c3ccc(cc3)Nc4ccc(cc4)OCC)C
LogP
-2.55 at · -2.55 at 20℃
CAS DataBase Reference
6104 · 6104-58-1(CAS DataBase Reference)
FDA UNII
1 ZRX790SI · M1ZRX790SI
EPA Substance Registry System
90 · C.I. Acid Blue 90 (6104-58-1)
UNSPSC Code
41105305 · 41105305
NACRES
1 · NC.01
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
271 · P271-P280
WGK Germany
3 · 3
TSCA
TSCA listed
HS Code
32041200 · 32041200
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Active

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk
3
tsca
TSCA listed
hs_code
32041200
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
REACH Registrations
Active
Precautionary statements
P271-P280
Absorption, Distribution and Excretion · 3 items

Due to the fact that this drug is administered by intravitreal injection and subsequently removed after staining, it is not expected to be significantly absorbed systemically.

This dye is removed in a clinical setting after the surgical procedure in which it was used.

This drug is administered via intravitreal injection and likely distributes only to parts of the eye.

Uses & manufacturing

UsesIndicators and reagents; [ChemIDplus]
Household ProductsInformation on 1 consumer products that contain C.I. Acid Blue 90 in the following categories is provided:
General Manufacturing InformationBenzenemethanaminium, N-[4-[[4-[(4-ethoxyphenyl)amino]phenyl][4-[ethyl[(3-sulfophenyl)methyl]amino]-2-methylphenyl]methylene]-3-methyl-2,5-cyclohexadien-1-ylidene]-N-ethyl-3-sulfo-, inner salt, sodium salt (1:1): ACTIVE
Applications · 2 items

UsesBrilliant Blue G is used in analytical biochemistry dye and as a P2X7 antagonist. It is also used in protein staining following gel electrophoresis. It is used to prepare the protein reagent for the determination of protein content of the collagenase enzyme isolated from fish waste. It may be employed as stain for the internal limiting membrane (ILM) for the macular hole (MH) and epiretinal membrane (ERM) surgery. It is useful for SDS gels as it readily stains proteins with minimal background color. Protein bands can be visualized during staining. It has been used in the Bradford dye-binding protein assay. A mechanism for dye binding to protein has been proposed, based on measuring Coomassie Brilliant Blue G-250 (CBBG) absorbance spectra during titration of the dye reagent in the absence of protein and its response to different polyamino acids. Brilliant Blue G has been used for determining critical micelle concentration of detergents.

General DescriptionBrilliant Blue G (BBG) is a dye. It has been proposed as a substitute for internal limiting membrane (ILM) peeling.

Preparation methods · 1 item

PreparationBenzaldehyde (1 Moore) and N-ethyl-N-benzyl-3-methylaniline(2 Moore) condensation, And then sulfonating the product of three acids, and lead oxide, peroxide, and then the reaction with the 4-Ethoxybenzenamine, Benzaldehyde sulfonic acid groups on the phenyl ring is substituted anilino-ethoxy.

Upstream & downstream products

Upstream raw materials

N-benzyl-N-ethyl m-toluidinePhenetidineEthylbenzyltoluidineTrisulfonic acidBenzaldehydePhenetidineEthylbenzyltoluidineBenzaldehyde

Downstream products

Acid blue 9 aluminum lakeErioglaucine disodium salt

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
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上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
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大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
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上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
南京美博生物科技有限公司025-58619198 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
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TCI AMERICA800-4238616 · [email protected]
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湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
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TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
Alfa Chemistry1-516-6625404 · [email protected]
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北京诺其雅盛生物科技有限公司4000-819-385 010-62329685 13718666987
九鼎化学(上海)科技有限公司4009209199 · [email protected]
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成都润泽本土化工有限公司028-88469284 18000562381 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006