Gallocyanine
Basic information
- CAS
1562-85-2- Standard SMILES
CN(C)c1ccc2[nH+]c3c(C(=O)O)cc(=O)c(O)c-3oc2c1.[Cl-]- InChIKey
AQSOTOUQTVJNMY-UHFFFAOYSA-N- Molecular formula
- C15H13ClN2O5
- Average molar mass
- 336.72 g/mol
- Monoisotopic mass
- 336.0512992
Overview
Gallocyanin is an organic chloride salt composed of 1-carboxy-7-(dimethylamino)-3,4-dihydroxyphenoxazin-5-ium and chloride ions in a 1:1 ratio. A histological dye used in solution with an iron alum mordant as a hematoxylin substitute in the H&E stain. It has a role as a fluorochrome and a histological dye. It contains a gallocyanin(1+).
Names & identifiers
- Preferred name
- Gallocyanine
- IUPAC
- 7-(dimethylamino)-4-hydroxy-3-oxophenoxazin-10-ium-1-carboxylic acid chloride
- English name
- GALLOCYANINE
- Molecular formula
- C15H13ClN2O5
- Molecular weight
- 336.73
Names & synonyms
GALLOCYANINE1562-85-2Gallocyanin1-Carboxy-7-(dimethylamino)-3,4-dihydroxyphenoxazin-5-ium chlorideSolid VioletGallocyanine BSGallocyanine DHC.I. Mordant Blue 10Fast VioletAnthracene Blue SWGGAlizarine Navy Blue ATBrilliant Chrome Blue P
Show more names
CI 51030FastBioletCI NO 51030solidvioletGallic bluegallocyaninebs
Mordant blue 10C.I. 51030Gallocyanine (chloride)7-(dimethylamino)-4-hydroxy-3-oxophenoxazin-10-ium-1-carboxylic acid;chloridePhenoxazin-5-ium, 1-carboxy-7-(dimethylamino)-3,4-dihydroxy-, chloride (1:1)8S1S2GY38KNSC-47701NSC-103779
Database identifiers
- CAS
1562-85-2- PubChem CID
- 73801
- DTXSID
DTXSID60935389- ChEMBL
CHEMBL1966521- ChEBI
CHEBI:90106
Properties
Computed structural properties
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 632
Physicochemical properties
- Density
- 1.3979 · 1.3979 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
- storage temp.
- room temp
- solubility
- PBS (pH 7.2): 10 mg/ml
- Colour Index
- 51030 · 51030
- form
- Fine Crystalline Powder
- color
- Very dark green to black
- Water Solubility
- 10 mg/ml), · Soluble in water (10 mg/ml), 100% ethanol (10 mg/ml), alcohol, 1N NH4OH (10 mg/ml), and DMSO (25 mg/ml).
- λmax
- 601 nm · 601 nm
- Merck
- 14 · 14,4355
- BRN
- 307454 · 307454
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- diagnostic assay manufacturinghematologyhistology
- InChI
- 1S/C15H12N2O5.ClH/c1-17(2)7-3-4-9-11(5-7)22-14-12(16-9)8(15(20)21)6-10(18)13(14)19;/h3-6H,1-2H3,(H2-,16,18,19,20,21);1H
- InChIKey
- ADAUKUOAOMLVSN-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- SP7692000
- hs_code
- 29349990
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H332-H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P261-P264-P270-P301+P312a-P304+P340-P501a
Chemistry & industry
Applications
UsesGallocyanine is used as an intermediate in chemical research. It is a small molecule dye that also inhibits DKK1 of the Wnt pathway.
UsesAs a dye; in alkali carbonate solution as a reagent for lead with which it forms a deep violet color.
General DescriptionGallocyanine belongs to the oxazine class of dyes. It is synthesised from methanol solution of gallic acid in the presence of excess iodine. Gallocyanine is used to stain animal cells, mostly the nucleic acids. It also acts as a chelating agent and is used to determine bioactive compounds and several metal ions.
Preparation methods
Preparationexcessive amounts of N,N-dimethyl-4-nitrosobenzenamine and3,4,5-Trihydroxybenzoic acid in methanol reaction (incomplete reaction in ethanol).
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Gallocyanin is an organic chloride salt composed of 1-carboxy-7-(dimethylamino)-3,4-dihydroxyphenoxazin-5-ium and chloride ions in a 1:1 ratio. A histological dye used in solution with an iron alum mordant as a hematoxylin substitute in the H&E stain. It has a role as a fluorochrome and a histological dye. It contains a gallocyanin(1+).
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