Product Code Database
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of and . Phloroglucinol is one of three isomeric . The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "natural phenol" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed . The enzyme is biosynthesized by phloroglucinol synthase.
A modern synthesis of phloroglucinol involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from trinitrobenzene.
As an enol, phloroglucinol in principle exists in equilibrium with keto . Evidence for this equilibrium is provided by the formation of the oxime:
For the neutral compound, the keto tautomers are undetectable spectroscopically. Upon deprotonation, the keto tautomer predominates.
The Hoesch reaction allows the synthesis of 1-(2,4,6-Trihydroxyphenyl)ethanone from phloroglucinol.
Leptospermone can be synthesized from phloroglucinol by a reaction with isovaleroylnitrile in the presence of a zinc chloride catalyst.
Pentacarbon dioxide, described in 1988 by Günter Maier and others, can be obtained by pyrolysis of 1,3,5-cyclohexanetrione (phloroglucin).
Phloroglucinol readily forms 5-aminoresorcinol (aka Phloramine) in aqueous ammonia at low temperatures.
Reaction of phloroglucinol and phloretic acid gives 30% yield of phloretin.
Phloroglucinols are secondary metabolites that occur naturally in certain plant species. It is also produced by brown algae and bacteria.
Acyl derivatives are present in the fronds of the coastal woodfern, Dryopteris arguta or in Dryopteris crassirhizoma. The anthelmintic activity of the root of Dryopteris filix-mas has been claimed to be due to flavaspidic acid, a phloroglucinol derivative.
Formylated phloroglucinol compounds (, and ) can be found in Eucalyptus species. Hyperforin and adhyperforin are two phloroglucinols found in St John's wort. Humulone is a phloroglucinol derivative with three isoprenoid side-chains. Two side-chains are prenyl groups and one is an isovaleryl group. Humulone is a bitter-tasting chemical compound found in the resin of mature hops ( Humulus lupulus).
, such as Ecklonia stolonifera, Eisenia bicyclis or species in the genus Zonaria, produce phloroglucinol and phloroglucinol derivatives. Brown algae also produce a type of tannins known as .
The bacterium Pseudomonas fluorescens produces phloroglucinol, phloroglucinol carboxylic acid and diacetylphloroglucinol.
The enzyme pyrogallol hydroxytransferase uses 1,2,3,5-tetrahydroxybenzene and 1,2,3-trihydroxybenzene (pyrogallol) to produce 1,3,5-trihydroxybenzene (phloroglucinol) and 1,2,3,5-tetrahydroxybenzene. It is found in the bacterium species Pelobacter acidigallici.
The enzyme phloroglucinol reductase uses dihydrophloroglucinol and NADP+ to produce phloroglucinol, NADPH, and H+. It is found in the bacterium species Eubacterium oxidoreducens.
The legume-root nodulating, microsymbiotic nitrogen-fixing bacterium species Bradyrhizobium japonicum is able to degrade catechin with formation of phloroglucinol carboxylic acid, further decarboxylated to phloroglucinol, which is dehydroxylated to resorcinol and hydroxyquinol.
Phloretin hydrolase uses phloretin and water to produce phloretate and phloroglucinol.
Phloroglucinols acylated derivatives have a fatty acid synthase inhibitory activity.
It is useful for the industrial synthesis of pharmaceuticals (Flopropione), Phloretin, and explosives (TATB (2,4,6-triamino-1,3,5-trinitrobenzene), trinitrophloroglucinol, 1,3,5-trinitrobenzeneA facile two-step Synthesis of 1,3,5-trinitrobenzene. Bottaro Jeffrey C, Malhotra Ripudaman and Dodge Allen, Synthesis, 2004, no 4, pages 499-500, ).
Phloroglucinolysis is an analytical technique to study by means of depolymerisation. The reaction makes use of phloroglucinol as nucleophile. formation (tannins condensation and precipitation) can be minimized in using strong nucleophiles, such as phloroglucinol, during pine tannins extraction.
Phloroglucinol is used in plant culture media. It demonstrates both cytokinin-like and auxin-like activity. Phloroglucinol increases shoot formation and somatic embryogenesis in several horticultural and grain crops. When added to rooting media together with auxin, phloroglucinol further stimulates rooting.
A solution of hydrochloric acid and phloroglucinol is also used for the detection of lignin (Wiesner test). A brilliant red color develops, owing to the presence of coniferaldehyde groups in the lignin.Lignin production and detection in wood. John M. Harkin, U.S. Forest Service Research Note FPL-0148, November 1966 ( article ) A similar test can be performed with tolonium chloride.
It is also part of Gunzburg reagent, an alcoholic solution of phloroglucinol and vanillin, for the qualitative detection of free hydrochloric acid in gastric juice.
ATC classification
It has the A03AX12 code in the A03AX Other drugs for functional bowel disorders section of the ATC code A03 Drugs for functional gastrointestinal disorders subgroup of the Anatomical Therapeutic Chemical Classification System. It also has the D02.755.684 code in the D02 Organic chemicals section of the Medical Subject Headings (MeSH) codes by the United States National Library of Medicine.
Applications
Phloroglucinol is mainly used as a coupling agent in printing. It links to give a fast black.
Use in tests
Phloroglucinol is a reagent of the Bernhard Tollens' test for . This test relies on reaction of the furfural with phloroglucinol to produce a colored compound with high molar absorptivity.Oshitna, K., and Tollens, B., Ueber Spectral-reactionen des Methylfurfurols. Ber. Dtsch. Chem. Ges. 34, 1425 (1901)
|
|
