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

Details

Stereochemistry ACHIRAL
Molecular Formula C20H14N2O10S3
Molecular Weight 538.528
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AMARANTH ACID

SMILES

OC1=C(\N=N\C2=C3C=CC=CC3=C(C=C2)S(O)(=O)=O)C4=CC=C(C=C4C=C1S(O)(=O)=O)S(O)(=O)=O

InChI

InChIKey=IRPXADUBAQAOKL-QURGRASLSA-N
InChI=1S/C20H14N2O10S3/c23-20-18(35(30,31)32)10-11-9-12(33(24,25)26)5-6-13(11)19(20)22-21-16-7-8-17(34(27,28)29)15-4-2-1-3-14(15)16/h1-10,23H,(H,24,25,26)(H,27,28,29)(H,30,31,32)/b22-21+

HIDE SMILES / InChI

Molecular Formula C20H14N2O10S3
Molecular Weight 538.528
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.ukfoodguide.net/e123.htm

Amaranth is an artificial dark red to purple azo dye. It is also used to color cosmetics. Amaranth is commonly used in fish roe, aperitif wine drinks and Americano. It has been banned in the United States since 1976 by the FDA, because it is a suspected carcinogen. Amaranth (E 123) is an azo dye authorised as a food additive in the EU and has previously been evaluated by the Joint FAO/WHO Expert Committee on Food Additives (JECFA) in 1972, 1975, 1978 and 1984, and by the EU Scientific Committee for Food (SCF) in 1976, 1979 and 1983. Derived from the small herbaceous plant of the same name. A purplish-red (blackcurrant) synthetic coal tar or azo dye found in ice creams, gravy granules, jams, jelly, tinned fruit pie fillings and prawns and packeted cake mixes, soups and trifles. It appears to cause allergic and/or intolerance reactions, similar to nettle rash, particularly amongst those with an aspirin intolerance or asthmatics. can provoke asthma, eczema and hyperactivity; it caused birth defects and foetal deaths in some animal tests, possibly also cancer. Not recommended for consumption by children. It is banned in Norway, United States, Russia and Austria with a very restricted use in France and Italy (caviar only).

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Hypersensitivity reactions to food colours with special reference to the natural colour annatto extract (butter colour).
1978
Toxicity of xanthene food dyes by inhibition of human drug-metabolizing enzymes in a noncompetitive manner.
2009
Effects of maternally exposed coloring food additives on receptor expressions related to learning and memory in rats.
2013 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:14:58 UTC 2023
Edited
by admin
on Fri Dec 15 20:14:58 UTC 2023
Record UNII
02J7X17ZUQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMARANTH ACID
Common Name English
C.I. ACID RED 27 FREE ACID
Common Name English
C.I. ACID RED 27 (FREE ACID)
Common Name English
1-(4-SULFONAPHTHYLAZO)-2-HYDROXYNAPHTHALENE-3,6-DISULFONIC ACID
Systematic Name English
2,7-NAPHTHALENEDISULFONIC ACID, 3-HYDROXY-4-(2-(4-SULFO-1-NAPHTHALENYL)DIAZENYL)-
Common Name English
Code System Code Type Description
RXCUI
1546381
Created by admin on Fri Dec 15 20:14:58 UTC 2023 , Edited by admin on Fri Dec 15 20:14:58 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
211-385-1
Created by admin on Fri Dec 15 20:14:58 UTC 2023 , Edited by admin on Fri Dec 15 20:14:58 UTC 2023
PRIMARY
EPA CompTox
DTXSID8048367
Created by admin on Fri Dec 15 20:14:58 UTC 2023 , Edited by admin on Fri Dec 15 20:14:58 UTC 2023
PRIMARY
FDA UNII
02J7X17ZUQ
Created by admin on Fri Dec 15 20:14:58 UTC 2023 , Edited by admin on Fri Dec 15 20:14:58 UTC 2023
PRIMARY
DAILYMED
02J7X17ZUQ
Created by admin on Fri Dec 15 20:14:58 UTC 2023 , Edited by admin on Fri Dec 15 20:14:58 UTC 2023
PRIMARY
CAS
642-59-1
Created by admin on Fri Dec 15 20:14:58 UTC 2023 , Edited by admin on Fri Dec 15 20:14:58 UTC 2023
PRIMARY