U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H6I4O5.2Na
Molecular Weight 879.8561
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERYTHROSINE SODIUM ANHYDROUS

SMILES

[Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C2=C3C=C(I)C(=O)C(I)=C3OC4=C(I)C([O-])=C(I)C=C24

InChI

InChIKey=IINNWAYUJNWZRM-UHFFFAOYSA-L
InChI=1S/C20H8I4O5.2Na/c21-11-5-9-13(7-3-1-2-4-8(7)20(27)28)10-6-12(22)17(26)15(24)19(10)29-18(9)14(23)16(11)25;;/h1-6,25H,(H,27,28);;/q;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula C20H6I4O5
Molecular Weight 833.8765
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Erythrosine B (also known as Red No. 3), a Food and Drug Administration (FDA)-approved red food dye, is found in cosmetics and food. It is also used as a plasma stain for nerve cells and staining bacteria in soil. It was studied the modulating capabilities of erythrosine B on amyloid-beta peptide (Aβ) aggregation and Aβ-associated impaired neuronal cell function. It is known, that aggregation Aβ is closely linked to the development of Alzheimer's disease pathology.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.2 µM [EC50]
0.66 µM [EC50]
0.57 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Multigeneration study of FD & C Red No. 3 (erythrosine) in Sprague-Dawley rats.
1990 Dec
Monosodium benzoate hypersensitivity in subjects with persistent rhinitis.
2004 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In order to determine the detrimental effects of rythrosine B (ER)-induced amyloid-beta peptide (Aβ) aggregates on cellular functions, it was chosen the cellular MTT reducing activity of Human neuroblastoma SH-SY5Y cells. Cells were adminstered Aβ aggregates preformed in the absence or presence of ER. Preformed Aβ aggregates were prepared by incubating 50 µM Aβ monomers in the absence or presence of various concentrations of ER (1x to 10x) at 37°C for the specified time duration. SH-SY5Y cells were incubated with 5 µM preformed aggregates for 48 hours, and subsequently MTT reducing activity was determined. The results suggested that ER mitigated Aβ-associated damage to the cellular function by blocking specific sequence of low molecular weight Aβ species that confers damages to neuronal cells. However, even at 10x ER the protofibrils formed are A11- and OC-reactive, suggesting that ER binding sites on the Aβ do not overlap with the epitope of either A11 or OC antibody.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:25:51 UTC 2023
Edited
by admin
on Fri Dec 15 15:25:51 UTC 2023
Record UNII
8TL7LH93FM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERYTHROSINE SODIUM ANHYDROUS
Common Name English
BENZOIC ACID, 2-(6-HYDROXY-2,4,5,7-TETRAIODO-3-OXO-3H-XANTHEN-9-YL)-, SODIUM SALT (1:2)
Common Name English
ERYTHROSINE, SODIUM ANHYDROUS
Common Name English
ERYTHROSINE [MI]
Common Name English
NSC-36685
Code English
DISODIUM SALT OF 2',4',5',7'-TETRAIODOFLUORESCEIN
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 120901
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
Code System Code Type Description
NSC
36685
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
SMS_ID
100000087004
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
PUBCHEM
27872
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
MERCK INDEX
m5019
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
RXCUI
1736634
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
FDA UNII
8TL7LH93FM
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
EVMPD
SUB20880
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
HSDB
7974
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
DAILYMED
8TL7LH93FM
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
CAS
16423-68-0
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
ECHA (EC/EINECS)
240-474-8
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
WIKIPEDIA
Erythrosine
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
CAS
568-63-8
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
ALTERNATIVE
EPA CompTox
DTXSID7021233
Created by admin on Fri Dec 15 15:25:51 UTC 2023 , Edited by admin on Fri Dec 15 15:25:51 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY