Indigoidine
Basic information
- CAS
2435-59-8- Standard SMILES
N=C1C=C(c2cc(N)c(=O)[nH]c2O)C(=O)NC1=O- InChIKey
YCZATMZTIWSFLZ-UHFFFAOYSA-N- Molecular formula
- C10H8N4O4
- Average molar mass
- 248.19 g/mol
- Monoisotopic mass
- 248.05455474
Overview
Indigoidine is a member of the class of pyridone that is a dimeric blue pigment biosynthesised from L-glutamine. It has a role as a biological pigment and a bacterial metabolite. It is a dicarboximide, a ring assembly, a pyridone and an enamine. It is functionally related to a L-glutamine.
Names & identifiers
- Preferred name
- Indigoidine
- IUPAC
- 3-(5-amino-2-hydroxy-6-oxo-1H-pyridin-3-yl)-5-iminopyridine-2,6-dione
- English name
- indigoidine
- Molecular formula
- C10H8N4O4
- Molecular weight
- 248.19
Names & synonyms
IndigoidineCHEBI:79296DTXSID9011254743-(5-amino-2-hydroxy-6-oxo-1H-pyridin-3-yl)-5-iminopyridine-2,6-dioneRefChem:148135DTXCID7015569942435-59-85,5'-Diamino-2H,2'H-[3,3'-bipyridinylidene]-2,2',6,6'(1H,1'H)-tetraoneIndigoidinVeretexyn BlueIndigoidine tautomer(5E)-3-amino-5-(5-amino-2,6-dioxopyridin-3-ylidene)pyridine-2,6-dione
Show more names
5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone2,6(1H,3H)-Pyridinedione, 5-amino-3-(5-amino-1,6-dihydro-2,6-dioxo-3(2H)-pyridinylidene)-
SCHEMBL16612487SCHEMBL16612491SCHEMBL29769725DTXSID4013594085,5'-Diamino-1H,1'H-[3,3'-bipyridinylidene]-2,2',6,6'-tetraoneMFCD361819475-Amino-3-(5-amino-1,2,3,6-tetrahydro-2,6-dioxopyridin-3-ylidene)-2,6(1H,3H)-pyridinedioneSY458168
Database identifiers
- CAS
2435-59-8- PubChem CID
- 193349
- DTXSID
DTXSID401359408- ChEBI
CHEBI:79296- Nikkaji
- J13.276D
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 145 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 597
Physicochemical properties
- Boiling point
- 285.6 · 285.6±40.0 °C(Predicted)
- Density
- 1.637 · 1.637±0.06 g/cm3(Predicted)
- pka
- 5.88 · 5.88±0.40(Predicted)
Chemistry & industry
Applications
DescriptionIndigoidine is a blue-violet organic pigment related to the Azaquinones group and synthesized by bacterial strains. It is biosynthesized by bacterial species such as Streptomyces chromofuscus，E. coli，and Corynebacterium insidiosum (Gangulyet al. 2019). It is used as a food colorant in cereal, baking, and ice-cream industries.
UsesIndigoidine natural blue dye is a promising alternative to the synthetic dyes used to colored jeans, leather, food, beverages, cosmetics and paper. The blue color of the indigoidine compound is bright and sustainable. As a natural dye, it has promising health benefits as an antioxidant and antimicrobial actor. Because of a new purification process patented with the compound, indigoidine natural blue dye is safe to use in food and drinks.
Additional notes
DefinitionChEBI: Indigoidine is a member of the class of pyridone that is a dimeric blue pigment biosynthesised from L-glutamine. It has a role as a bacterial metabolite and a biological pigment. It is a pyridone, a ring assembly, a dicarboximide and an enamine. It derives from a L-glutamine.
DefinitionPigment characterization:Identification of interrupted genes in the nonpigmented mutants suggested that the blue compound produced by Y4I was indigoidine, a bicyclic 3,3′-bipyridyl molecule synthesized by the cyclization of two glutamine molecules. The absorbance spectrum of the purified compound in DMSO has a peak at 612 nm, which has been previously reported as the absorbance maximum of indigoidine. Profiles of the Y4I variant show that absorbance at this wavelength for the clpA::Tn5 mutant is approximately five times higher than that of the wild-type strain[1].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…