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Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, but they cannot be by any scientifically-accepted definition.
Phloroglucinol is a useful intermediate because it is polyfunctional. Furthermore, the deprotonated intermediate in the interconversion of the two forms, referred to as an enolate anion, is important in carbonyl chemistry, in large part because it is a strong nucleophile.
From water, phloroglucinol crystallizes as the dihydrate, which has a melting point of 116-117 °C, but the anhydrous form melts at a much higher temperature, at 218-220 °C. It does not boil intact, but it does sublime.
It is synthesized via a number of processes, but representative is the following route from trinitrobenzene. It is a selective trinitration where benzene is symmetrically trinitrated to 1,3,5 trinitrobenzene to produce a precursor for the synthesis of phloroglucinol.
The synthesis is noteworthy because ordinary aniline derivatives are unreactive toward hydroxide. Because the triaminobenzene also exists as its imine tautomer, it is susceptible to hydrolysis.
The compound behaves like a ketone in its reaction with hydroxylamine, forming the tris(oxime). But it behaves also like a benzenetriol (Ka1 = 3.56 × 10-9, Ka2 1.32×10-9), as the three hydroxyl groups can be methylated to give 1,3,5-trimethoxybenzene.
It is also used as a treatment for gallstones, spasmodic pain and other related gastrointestinal disorders. It has a non-specific spasmolytic action on the vessels, bronchi, intestine, ureters and gall bladder, and is used for treating disorders of these organs. It is the main ingredient of the drug Spasfon, commercialized in France, where it is one of the most sold drugs.
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 D02Organic chemicals section of the Medical Subject Headings (MeSH) codes by the United States National Library of Medicine.
Phloroglucinol is mainly used as a coupling agent in printing. It links diazo dyes to give a fast black.
Phloroglucinolysis is an analytical technique to study condensed tannins by means of depolymerisation. The reaction makes use of phloroglucinol as nucleophile. Phlobaphenes formation (tannins condensation and precipitation) can be minimized in using strong nucleophiles, such as phloroglucinol, during pine tannins extraction.
Use in tests
Phloroglucinol is a reagent of the Tollens' test for pentoses. This test relies on reaction of the furfural with phloroglucinol to produce a colored compound with high molar absorptivity.
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. 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.
Hlasiwetz, Heinrich (1855). "Ueber das Phloretin" [On phloretin]. Annalen der Chemie und Pharmacie. 96 (1): 118-123. doi:10.1002/jlac.18550960115. On p. 120, Hlasiwetz named phloroglucin: "Die auffalendste Eigenschaft dieses Körpers ist, dass er überaus süss schmeckt, wesshalb er bis auf weiteres Phloroglucin genannt sein mag." (The most striking property of this substance is that it tastes extremely sweet, for which reason it may be named "phloroglucin" until further [information emerges].)
Thorpe, Edward, ed., A Dictionary of Applied Chemistry (London, England: Longmans, Green, and Co., 1913), vol. 4, 183.
^Maier, G.; Reisenauer, H. P.; Schäfer, U.; Balli, H. (1988). "C5O2 (1,2,3,4-Pentatetraene-1,5-dione), a New Oxide of Carbon". Angewandte Chemie International Edition. 27 (4): 566-568. doi:10.1002/anie.198805661.
^ abNa, M.; Jang, J.; Min, B. S.; Lee, S. J.; Lee, M. S.; Kim, B. Y.; Oh, W. K.; Ahn, J. S. (2006). "Fatty acid synthase inhibitory activity of acylphloroglucinols isolated from Dryopteris crassirhizoma". Bioorganic & Medicinal Chemistry Letters. 16 (18): 4738-4742. doi:10.1016/j.bmcl.2006.07.018. PMID16870425.
^Eschler, B. M.; Pass, D. M.; Willis, R.; Foley, W. J. (2000). "Distribution of foliar formylated phloroglucinol derivatives amongst Eucalyptus species". Biochemical Systematics and Ecology. 28 (9): 813-824. doi:10.1016/S0305-1978(99)00123-4. PMID10913843.
^Okada, Y.; Ishimaru, A.; Suzuki, R.; Okuyama, T. (2004). "A New Phloroglucinol Derivative from the Brown AlgaEisenia bicyclis: Potential for the Effective Treatment of Diabetic Complications". Journal of Natural Products. 67 (1): 103-105. doi:10.1021/np030323j. PMID14738398.
^Blackman, A. J.; Rogers, G. I.; Volkman, J. K. (1988). "Phloroglucinol Derivatives from Three Australian Marine Algae of the Genus Zonaria". Journal of Natural Products. 51: 158-160. doi:10.1021/np50055a027.
^Shibata, T.; Kawaguchi, S.; Hama, Y.; Inagaki, M.; Yamaguchi, K.; Nakamura, T. (2004). "Local and chemical distribution of phlorotannins in brown algae". Journal of Applied Phycology. 16 (4): 291. doi:10.1023/B:JAPH.0000047781.24993.0a.
^ abAchkar, J.; Xian, M.; Zhao, H.; Frost, J. W. (2005). "Biosynthesis of Phloroglucinol". Journal of the American Chemical Society. 127 (15): 5332-5333. doi:10.1021/ja042340g. PMID15826166.
^A facile two-step Synthesis of 1,3,5-trinitrobenzene. Bottaro Jeffrey C, Malhotra Ripudaman and Dodge Allen, Synthesis, 2004, no 4, pages 499-500, INIST:15629637
^Sealy-Fisher, V. J.; Pizzi, A. (1992). "Increased pine tannins extraction and wood adhesives development by phlobaphenes minimization". Holz als Roh- und Werkstoff. 50 (5): 212. doi:10.1007/BF02663290.
^Oshitna, K., and Tollens, B., Ueber Spectral-reactionen des Methylfurfurols. Ber. Dtsch. Chem. Ges. 34, 1425 (1901)
^Lignin production and detection in wood. John M. Harkin, U.S. Forest Service Research Note FPL-0148, November 1966 (article)