5699. Malachite Green

Nomenclature

CAS number: 569-64-2; 510-13-4 (carbinol base)
N-[4-[[4-(Dimethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-methylmethanaminium chloride; bis[p-(dimethylamino)phenyl]phenylmethylium chloride; C.I. Basic Green 4; C.I. 42000; aniline green; benzal green; benzaldehyde green; china green; diamond green B; diamond green Bx; diamond green P extra; fast green; light green N; new victoria green extra O; new victoria green extra I; new victoria green extra II; solid green O; victoria green W; victoria green B.
C23H25ClN2; mol wt 364.91.
C 75.70%, H 6.91%, Cl 9.72%, N 7.68%.

Description and references

Triphenylmethane dye with fungicidal and limited antiseptic activity. Prepn: Colour Index Vol. 4 (3rd ed., 1971) p 4380. Conformational changes in excited state: S. Saikan, J. Sei, J. Chem. Phys. 79, 4154 (1983). Use in electron microscopy: R. G. Pourcho et al., Stain Technol. 53, 29 (1978); as stain in determn of prostaglandin E and F compounds: E. J. Singh et al., J. Chromatogr. 105, 195 (1975); in determn of inorganic phosphate: W. Hohenwallner, E. Wimmer, Clin. Chim. Acta 45, 169 (1973); S. G. Carter, D. W. Karl, J. Biochem. Biophys. Methods 7, 7 (1982). Antiseptic activity: J. E. Madden et al., Surg. Forum 22, 63 (1971). Toxicology: N. Brock, A. Erhardt, Arzneim.-Forsch. 1, 5 (1951); T. D. Bills, L. L. Marking, Invest. Fish Control 75, 6 (1977); S. Clemmensen et al., Arch. Toxicol. 56, 43 (1984). Reviews of use as fungicide in fish culture: N. C. Nelson, U.S. NTIS Report (PB-235450, 1974) 79 pp, C.A. 82, 150006p (1975), (PB-235451, 1974) 33 pp, C.A. 83, 1547j (1975); and as biological stain: Conn's Biological Stains, R. W. Horobin, J. A. Kiernan, Eds. (BIOS Scientific Publishers Ltd, Oxford, UK, 10th ed., 2002) 189-190. Review of toxicological effects: S. Srivastava et al., Aquat. Toxicol. 66, 310-329 (2004).

Chemical structure

Properties

Green crystals with metallic luster. Very sol in water; sol in alcohol, methanol, amyl alcohol. Water solns are blue-green, absorption max 616.9 nm; yellow below pH 2. pK 6.90. LD50 in mice (mg/kg): 80 orally; 4.2 i.p. (Brock, Erhardt). LC50 (6 hr, 12°C) in bluegill sunfish, channel catfish, rainbow trout, coho salmon (mg/l): 2.19 (pH 7.5), 0.960 (pH 7.5), 6.8 (pH 8.0), 3.0 (pH 7.5) (Bills, Marking).

Derivative

Oxalate salt.

Nomenclature

CAS number: 2437-29-8
C46H50N4.2HC2O4.C2H2O4; mol wt 927.00.
C 67.37%, H 5.87%, N 6.04%, O 20.71%.

Properties

Sol to 4% in water, 5% in ethanol. Insol in xylene.

Derivative

Leucomalachite green.

Nomenclature

CAS number: 129-73-7
Bis(p-dimethylaminophenyl)phenylmethane.
C23H26N2; mol wt 330.47.
C 83.59%, H 7.93%, N 8.48%.

Properties

Colorless, reduced form of malachite green. Practically insol in water. Slightly sol in ethanol.

Note

The term malachite green applies to the oxalate as well as the chloride.

Use

For directly dyeing silk, wool, jute and leather; dyeing cotton after mordanting. Biological stain. Clinical reagent (inorganic phosphate assay). As spot test reagent for detecting sulfurous acid and cerium. As acid-base indicator: pH 0.0 yellow, 2.0 green; 11.6 green, 14 colorless.

Therapeutic Category (Veterinary)

Fungicide and parasiticide in fish.