The colourful history of malachite green: from ancient Egypt to modern surgery

‘Brilliant green’, also known as ‘malachite green G’ (C 27 H 33 N 2 HO 4 S: ethanaminium, N -[4-[[4-(diethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]- N -ethyl sulphate), has long been utilized as an ink and as a dye for artistic, medical, and industrial purposes ( Fig. 1 ) . Current preparations of brilliant green ink and dye do not contain malachite, but are chemically prepared as anhydrous salts using a process initially described by Fischer in 1877 . The term ‘malachite’ (Gk. molochitēs ) reflects the green colour of the leaves of the Malvaceae family of plants.

Fig. 1
(A) The chemical structure of brilliant green dye (malachite green G) contains three benzyl rings with alkyl amino groups. (B) Malachite green is similar, with modifications in the structure of the alkyl amino groups. Both compounds have a green hue in solution, similar to the colour of the mineral malachite.

A basic copper carbonate (Cu 2 CO 3 (OH) 2 ), mineral malachite was mined from deposits near the Isthmus of Suez and the Sinai as early as 4000 BC . Beauty was considered a sign of holiness among the ancient Egyptians. Cosmetic enhancement with make-up was integral to their daily life . Malachite green paint was frequently applied as an ‘eye-liner’ and used to adorn the nipple–areola complex in the early pre-dynastic period (i.e. prior to 3100 BC) . The Egyptians believed that malachite prevented water-borne eye infections that were common along the Nile river . They also thought that the medicinal properties of malachite were magical and holy. Cosmetic palettes have been found buried with the deceased and the ink was used to paint mural hieroglyphs in tombs .

Over the subsequent millennia, malachite green dyes became a standard for colouring fabrics, paper, and leather . Malachite green has also been used to catch thieves . The anhydrous form of the chemical is applied as bait to paper money. Anyone handling stolen money would be caught ‘green-handed’ upon washing . Today, the dye is commonly used to colour silk and wool.

The medicinal properties of brilliant green solutions were studied in the early 20th century . Browning and colleagues demonstrated that brilliant green also exhibited bactericidal activity against Gram-positive organisms, particularly cocci ; their results were verified by other investigators . Its bacteriostatic activity has been ascribed to the three benzyl rings with two alkyl amine groups . Baccal used brilliant green ink solution for preoperative skin preparation, hand-washing before surgical procedures, and sterilization of catgut sutures and surgical instruments . He also used the solution for topical treatment of burns and inflammatory diseases of the ocular adnexa. These various clinical reports were confirmed experimentally by Narat, who showed that brilliant green is a strong, non-irritating, non-toxic antiseptic with excellent penetration . Narat also believed that the solution stimulated the formation of healthy granulation tissue. In Russia and Eastern Europe, diluted brilliant green solution is still sold as a topical antiseptic (Latin: Viridis nitentis spirituosa , Russian: Zelyonka) .

In the early 20th century, ink for cutaneous marking was first used in the emerging specialty of plastic surgery . Victor Bonney, a British gynaecologist, mixed malachite green and gentian violet as an antiseptic solution for vaginal procedures . ‘Bonney’s blue’ became a popular marking ink among British and European plastic surgeons . In 1928, Vilray Blair used methylene blue to draw his Mirault-type cleft lip repair . In 1929, John Staige Davis, the first plastic surgeon at The Johns Hopkins Hospital, used 5% brilliant green to mark excisions for scar revision and for tattooing the conchal cartilage during setback otoplasty . He wrote that “…perforating the tissues with the needle dipped in brilliant green solution in marking out the line of cartilage to be incised, or excised, is a distinct advance in technique” .

Over the ensuing decades, brilliant green ink continued to be a favourite at the plastic surgery service of The Johns Hopkins Hospital. Past chairmen, Milton Edgerton (1951–1970), Jack Hoopes (1971–1990), and Paul Manson (1991–2011), all used brilliant green for cutaneous and mucosal marking. In 1974, brilliant green was introduced at Boston Children’s Hospital by a Hopkins graduate (JBM). As a result of the integration of plastic surgery and oral surgery at the Children’s Hospital, brilliant green was adopted by a maxillofacial surgeon (LBK) to mark mucosal incisions and osteotomies. In 1980, he switched to a sterile pencil for bone marking.

The currently used brilliant green ink is soluble in water and alcohol . Preparation concentrations vary from 0.5% to 5.0% . Cutaneous and mucosal marks can be removed easily with ethyl alcohol. Hydrogen peroxide helps to clean linens that are soiled with the product. Brilliant green ink is not easily soluble in povidone iodine or light saline irrigation. It can also be used to mark a mucosal surface and, once dry, it does not bleed into the surrounding tissues. In contrast, commercial surgical marking pens contain gentian violet in isopropyl alcohol (1–12%). Their disadvantage (also an advantage) is that the markings are nearly insoluble and difficult to erase. However, the tip diameters of commercial marking pens are too wide for drawing fine lines, such as those needed for cleft lip repair ( Fig. 2 ). A sharpened toothpick (bamboo preferred over pine) dipped in brilliant green ink and in steady hands, gives a delicate line. The ink is particularly useful in marking mucosa (keratinized or non-keratinized) for intraoral incisions ( Fig. 3 ). Because brilliant green is a tincture, it can be easily erased with a drop of ethanol. Gentian violet and methylene blue, which are commonly prepared as aqueous solutions, too easily wash off of skin and mucosa with water and saliva.

Dec 14, 2017 | Posted by in Oral and Maxillofacial Surgery | Comments Off on The colourful history of malachite green: from ancient Egypt to modern surgery
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