HOME

TheInfoList



OR:

Methyl red (2-(''N'',''N''-dimethyl-4-aminophenyl) azobenzenecarboxylic acid), also called C.I. Acid Red 2, is an
indicator Indicator may refer to: Biology * Environmental indicator of environmental health (pressures, conditions and responses) * Ecological indicator of ecosystem health (ecological processes) * Health indicator, which is used to describe the health o ...
dye that turns red in
acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...
ic solutions. It is an
azo dye Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N ...
, and is a dark red crystalline powder. Methyl red is a
pH indicator A pH indicator is a halochromic chemical compound added in small amounts to a solution so the pH (acidity or basicity) of the solution can be determined visually or spectroscopically by changes in absorption and/or emission properties. Hence, ...
; it is red in pH under 4.4, yellow in pH over 6.2, and orange in between, with a p''K''a of 5.1.
Murexide Murexide (NH4C8H4N5O6, or C8H5N5O6·NH3), also called ammonium purpurate or MX, is the ammonium salt of purpuric acid. It is a purple solid that is soluble in water. The compound was once used as an indicator reagent. Aqueous solutions are yel ...
and methyl red are investigated as promising enhancers of sonochemical destruction of
chlorinated hydrocarbon An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlo ...
pollutant A pollutant or novel entity is a substance or energy introduced into the environment that has undesired effects, or adversely affects the usefulness of a resource. These can be both naturally forming (i.e. minerals or extracted compounds like oi ...
s. Methyl red is classed by the
IARC IARC may refer to: * International Aerial Robotics Competition * International Age Rating Coalition * International Agency for Research on Cancer * International Arctic Research Center * Israel Amateur Radio Club The Israel Amateur Radio Club (IA ...
in
group 3 Group 3 may refer to: *Group 3 element, chemical element classification *Group 3 (racing), FIA classification for auto racing *Group 3, the third tier of races in worldwide Thoroughbred horse racing * Group 3 image format, Group 3 & Group 4 are d ...
- unclassified as to
carcinogenic A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...
potential in humans.


Preparation

As an azo dye, methyl red may be prepared by
diazotization Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. General properti ...
of
anthranilic acid Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ''ortho''-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic f ...
, followed by reaction with
dimethylaniline ''N'',''N''-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It consists of a tertiary amine, featuring dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but comm ...
: :


Properties

Methyl red displays pH dependent
photochromism Photochromism is the reversible transformation of a chemical species (photoswitch) between two forms by the absorption of electromagnetic radiation (photoisomerization), where the two forms have different absorption spectra. In plain language, th ...
, with protonation causing it to adopt a
hydrazone Hydrazones are a class of organic compounds with the structure . They are related to ketones and aldehydes by the replacement of the oxygen =O with the = functional group. They are formed usually by the action of hydrazine on ketones or aldehydes. ...
/
quinone The quinones are a class of organic compounds that are formally "derived from aromatic compounds
uch as benzene or naphthalene Uch ( pa, ; ur, ), frequently referred to as Uch Sharīf ( pa, ; ur, ; ''"Noble Uch"''), is a historic city in the southern part of Pakistan's Punjab province. Uch may have been founded as Alexandria on the Indus, a town founded by Alexand ...
by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double ...
structure. : Methyl Red has a special use in histopathology for showing acidic nature of tissue and presence of organisms with acidic natured cell walls. Methyl Red is detectably fluorescent in 1:1 water:methanol (pH 7.0), with an emission maximum at 375 nm (
UVA UVA most often refers to: * Ultraviolet A, a type of ultraviolet radiation * University of Virginia, a public research university in Charlottesville, Virginia, United States Uva or UVA may also refer to: Places * Uva, Missouri, an unincorpora ...
) upon excitation with 310 nm light (
UVB Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30  PHz) to 400 nm (750  THz), shorter than that of visible light, but longer than X-rays. UV radiation i ...
).


Methyl red test

In
microbiology Microbiology () is the scientific study of microorganisms, those being unicellular (single cell), multicellular (cell colony), or acellular (lacking cells). Microbiology encompasses numerous sub-disciplines including virology, bacteriology, prot ...
, methyl red is used in the
methyl red test Methyl red (2-(''N'',''N''-dimethyl-4-aminophenyl) azobenzenecarboxylic acid), also called C.I. Acid Red 2, is an indicator dye that turns red in acidic solutions. It is an azo dye, and is a dark red crystalline powder. Methyl red is a pH indi ...
(MR test), used to identify
bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...
producing stable acids by mechanisms of mixed acid
fermentation Fermentation is a metabolic process that produces chemical changes in organic substrates through the action of enzymes. In biochemistry, it is narrowly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food ...
of
glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using ...
(''cf.'' Voges–Proskauer test). The MR test, the "M" portion of the four
IMViC The IMViC tests are a group of individual tests used in microbiology lab testing to identify an organism in the coliform group. A coliform is a gram negative, aerobic, or facultative anaerobic rod, which produces gas from lactose within 48 hour ...
tests, is used to identify enteric bacteria based on their pattern of glucose metabolism. All enterics initially produce
pyruvic acid Pyruvic acid (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH3COCOO−, is an intermediate in several metabolic pathways throughout the cell. Pyruvic aci ...
from glucose metabolism. Some enterics subsequently use the mixed acid pathway to metabolize pyruvic acid to other acids, such as lactic, acetic, and formic acids. These bacteria are called methyl-red positive and include ''
Escherichia coli ''Escherichia coli'' (),Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. also known as ''E. coli'' (), is a Gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escher ...
'' and ''
Proteus vulgaris ''Proteus vulgaris'' is a rod-shaped, nitrate-reducing, indole-positive and catalase-positive, hydrogen sulfide-producing, Gram-negative bacterium that inhabits the intestinal tracts of humans and animals. It can be found in soil, water, and feca ...
''. Other enterics subsequently use the butylene glycol pathway to metabolize pyruvic acid to neutral end products. These bacteria are called methyl-red-negative and include ''
Serratia marcescens ''Serratia marcescens'' () is a species of rod-shaped, Gram-negative bacteria in the family Yersiniaceae. It is a facultative anaerobe and an opportunistic pathogen in humans. It was discovered in 1819 by Bartolomeo Bizio in Padua, Italy.Serrati ...
'' and ''
Enterobacter aerogenes ''Klebsiella aerogenes'', previously known as ''Enterobacter aerogenes,'' is a Gram-negative, oxidase negative, catalase positive, citrate positive, indole negative, rod-shaped bacterium. The bacterium is approximately 1-3 microns in length, and ...
''.


Process

A tube filled with a glucose phosphate broth is inoculated with a sterile transfer loop. The tube is incubated at for 2–5 days. After incubation, 2.5 ml of the medium are transferred to another tube. Five drops of the pH indicator methyl red is added to this tube. The tube is gently rolled between the palms to disperse the methyl red.


Expected results

Enterics that subsequently metabolize pyruvic acid to other acids lower the pH of the medium to 4.2. At this pH, methyl red turns red, a positive test. Enterics that subsequently metabolize pyruvic acid to neutral end products lower the pH of the medium to only 6.0. At this pH, methyl red is yellow, a negative test.


See also

*
Methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...
*
Universal Indicator __FORCETOC__ A universal indicator is a pH indicator made of a solution of several compounds that exhibits several smooth colour changes over a wide range pH values to indicate the acidity or alkalinity of solutions. Although there are several ...
*
Tashiro's indicator Tashiro's indicator is a pH indicator (pH value: 4.4–6.2), mixed indicator composed of a solution of methylene blue (0.1%) and methyl red (0.03%) in ethanol or in methanol. Used e.g. for the titration of ammonia in Kjeldahl analysis. Colours * I ...
*
pH indicator A pH indicator is a halochromic chemical compound added in small amounts to a solution so the pH (acidity or basicity) of the solution can be determined visually or spectroscopically by changes in absorption and/or emission properties. Hence, ...
s *
Methyl yellow Methyl yellow, or C.I. 11020, is an organic compound with the formula C6H5N2C6H4N(CH3)2. It is an azo dye derived from dimethylaniline. It is a yellow solid. According to X-ray crystallography, the C14N3 core of the molecule is planar. It is u ...
*
Methyl orange Methyl orange is a pH indicator frequently used in titration because of its clear and distinct color variance at different pH values. Methyl orange shows red color in acidic medium and yellow color in basic medium. Because it changes color at the ...
*
Methyl violet Methyl violet is a family of organic compounds that are mainly used as dyes. Depending on the number of attached methyl groups, the color of the dye can be altered. Its main use is as a purple dye for textiles and to give deep violet colors in p ...


References

*"Microbiology, A Photographic Atlas for the Laboratory", Alexander, Street, Pearson Education, 2001.


External links


Nile Chemicals -- Methyl Red
A site showing some extra information on methyl red.
Synthesis of methyl red
{{Clinical microbiology techniques IARC Group 3 carcinogens PH indicators Azo dyes Anthranilic acids Dimethylamino compounds