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Sigma-Aldrich

Malachite Green oxalate salt

for microscopy, crystalline, S. No.: 754

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Synonym(s):
N,N,N′,N′-Tetramethyl-4,4′-diaminotriphenylcarbenium oxalate, Basic Green 4
Empirical Formula (Hill Notation):
C23H25N2 · C2HO4 · 0.5C2H2O4
CAS Number:
2437-29-8
Molecular Weight:
463.50
Colour Index Number:
42000
Beilstein:
3644550
EC Number:
219-441-7
UNSPSC Code:
12171500
PubChem Substance ID:
57648708
NACRES:
MA.02

grade

for microscopy

Quality Level

200

form

crystalline

color

S. No.: 754

mp

144-150 °C

solubility

methanol: 0.01 g/10 mL, blue to very deep blue

εmax

≥1450 at 609-619 nm in water
≥300 at 420-430 nm in water

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

C[N+](C)=C1C=CC(C=C1)=C(C2=CC=C(N(C)C)C=C2)C3=CC=CC=C3.[O-]C(C(O)=O)=O

InChI

1S/C23H25N2.C2H2O4/c1-24(2)21-14-10-19(11-15-21)23(18-8-6-5-7-9-18)20-12-16-22(17-13-20)25(3)4;3-1(4)2(5)6/h5-17H,1-4H3;(H,3,4)(H,5,6)/q+1;/p-1

InChI key

REZFCYOVFCJTDG-UHFFFAOYSA-M

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General description

Malachite green is manufactured as a zinc-free oxalate salt (green crystals with a metallic sheen) or as a zinc chloride salt (yellow crystals). Malachite green comes under the triphenyl methane class of dyes and is one of the most effective agents traditionally known for treating water mold infections of fish and eggs. It has also been found to be effective against ectoparasites, protozoan and some myxozoan parasites. Though it has several disadvantages like it acts as respiratory poison, teratogen and suspected carcinogen. It generated free radicals, thereby making it highly toxic to mammalian cells in culture; it also causes malignant transformation. It has a long half-life and can persist in tissues for long periods. In water, malachite green exists in equilibrium between the colored, ionic form and the colorless, nonionic pseudobase (carbinol form). Only the colored ionic form has antimicrobial activity, whereas the carbinol form is lipid-soluble, hence allowing it to pass across membranes. The toxicity of malachite green is dependent on temperature and it increase with increase in temperature, whereas it is more toxic at low pH and low hardness. It is phyotoxic in nature, thereby it is inactivated (oxidised) by light.

Application

Malachite green oxalate salt was used in studying the photocatalytic degradation with TiO2/WO3. It was also used in preparing selective medium for isolating Verticillium fungicola from mushroom. It may be used for the determination of phosphate in serum. It may also be used to monitor the presence of free COOH on the solid-phase. It may be used as reference materials for in an analytical method to independently quantify malachite green oxalate and leucomalachite green in fish tissue. It may also be used in Rappaport broth for incubating the membrane filters used in detecting Salmonella sp.

Other Notes

The molecular mass of malachite green oxalate is expressed as either:
927.00 g/mol - the mass of 2 mol malachite green + 2 mol monohydrogen oxalate + 1 mol dihydrogen oxalate, or
463.50 g/mol - the mass of 1 mol malachite green + 1 mol monohydrogen oxalate + 0.5 mol dihydrogen oxalate

Signal Word

Danger

Hazard Statements

H301,H318,H361fd,H410

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Repr. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A selective medium for Verticillium fungicola.
Rinker, D. L., S. Bussmann, and G. Aim.
Canadian Journal of Plant Pathology, 15, 123-124 (1993)
Photocatalytic degradation of malachite green dyes with TiO2/WO3 composite.
Bojinova, Assya S., et al.
Eurasian Journal of Analytical Chemistry, 3, 34-43 (2008)
Malachite green, a valuable reagent to monitor the presence of free COOH on the solid-phase.
Attardi ME
Tetrahedron Letters, 41 (38), 7391-7394 (2000)
A Kallner
Clinica chimica acta; international journal of clinical chemistry, 59(1), 35-39 (1975-02-22)
The highly sensitive malachite-green method for the determination of phosphate requires a protective colloid in order to avoid precipitation of the formed dye salt. A polyvinylalcohol proved to be suitable and permit the determination of phosphate in urine and in
Fish Disease: Diagnosis and Treatment.
Noga EJ.
Science (2011)
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