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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 459115668
			| verifiedrevid = 459445024
	| Name = Phloroglucinol
	| ImageFileL1 = phloroglucinol structure.png		| Name = Phloroglucinol
			| ImageFileL1 = phloroglucinol structure.png
			| ImageFileR1 = Phloroglucinol-3D.png
	| ImageSizeL1 = 120px
			| PIN = Benzene-1,3,5-triol
	| ImageFileR1 = Phloroglucinol-3D.png
			| OtherNames = phloroglucine,
	| ImageSizeR1 = 120px
			1,3,5-benzenetriol , 1,3,5-trihydroxybenzene or cyclohexane-1,3,5-trione
	| IUPACName = Benzene-1,3,5-triol
			|Section1={{Chembox Identifiers
	| OtherNames = phloroglucine, 1,3,5-trihydroxybenzene, 1,3,5-benzenetriol, or cyclohexane-1,3,5-trione
			| UNII_Ref = {{fdacite|correct|FDA}}
	| Section1 = {{Chembox Identifiers
	| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = DHD7FFG6YS		| UNII = DHD7FFG6YS
	| ChEMBL = 473159		| KEGG = D00152
			| KEGG2 = C02183
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| ChEMBL = 473159
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 16204		| ChEBI = 16204
	| PubChem = 359		| PubChem = 359
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 352		| ChemSpiderID = 352
	| SMILES = c1c(cc(cc1O)O)O		| SMILES = c1c(cc(cc1O)O)O
	| InChI = 1/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H		| InChI = 1/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
	| InChIKey = QCDYQQDYXPDABM-UHFFFAOYAF		| InChIKey = QCDYQQDYXPDABM-UHFFFAOYAF
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H		| StdInChI = 1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = QCDYQQDYXPDABM-UHFFFAOYSA-N		| StdInChIKey = QCDYQQDYXPDABM-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 108-73-6		| CASNo = 108-73-6
	| ChEMBL = 473159		| RTECS = UX1050000
	| ChEBI = 16204		| EINECS = 203-611-2
	| PubChem = 359
	| RTECS = UX1050000
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>3</sub>		| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>3</sub>
	| MolarMass = 126.11 g/mol		| MolarMass = 126.11 g/mol
			| Appearance = colorless to beige solid
	| ExactMass = 126.031694
			| Density =
	| Appearance = white solid
			| Solubility = 1 g/100 mL
	| Density =
			| SolubleOther = soluble in ], ], ]
	| Solubility = 1 g/100 mL
			| MeltingPtC = 219
	| MeltingPt = 218-220 °C
			| pKa = 8.45
			| MagSus = -73.4·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| Dipole =		| Dipole =
	}}		}}
	| Section7 = {{Chembox Hazards		|Section6={{Chembox Pharmacology
			| ATCCode_prefix = A03
	| ExternalMSDS =
			| ATCCode_suffix = AX12
	| EUClass = Harmful ('''Xn''')
			}}
	| NFPA-H =
			|Section7={{Chembox Hazards
	| NFPA-F =
	| NFPA-R =		| ExternalSDS =
	| RPhrases =		| NFPA-H =
	| SPhrases =		| NFPA-F =
	| FlashPt =		| NFPA-R =
			| GHSPictograms = {{GHS07}}{{GHS08}}
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|315|317|319|335|341|361}}
			| PPhrases = {{P-phrases|201|202|261|264|271|272|280|281|302+352|304+340|305+351+338|308+313|312|321|332+313|333+313|337+313|362|363|403+233|405|501}}
			| FlashPt =
			| LD50 = 5 g/kg (rat, oral)
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
			| OtherFunction_label =
	| Function =
	| OtherFunctn =		| OtherFunction =
	| OtherCpds =		| OtherCompounds =
	}}		}}
	}}		}}
			]
			'''Phloroglucinol''' is an ] with the formula C<sub>6</sub>H<sub>3</sub>(OH)<sub>3</sub>. It is a colorless solid. It is used in the ] of ]s and ]s. Phloroglucinol is one of three isomeric ]s. The other two isomers are ] (1,2,4-benzenetriol) and ] (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "]s" according to the ] official nomenclature rules of chemical compounds. Many such monophenolics are often termed ]s.
			==Synthesis and occurrence==
	'''Phloroglucinol''' is a ]. It is an organic compound that is used in the ] of ]s and ]s. This molecule exists in two forms, or ]s, '''1,3,5-trihydroxybenzene''', which has ]-like, and '''1,3,5-cyclohexanetrione''' (phloroglucin), which has ]-like character. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional.
			In 1855, phloroglucinol was first prepared from ] by the Austrian chemist ] (1825–1875).<ref>{{cite journal|last1=Hlasiwetz|first1=Heinrich|title=Ueber das Phloretin|journal=Annalen der Chemie und Pharmacie|date=1855|volume=96 |issue= 1 |pages= 118–123 |url=https://babel.hathitrust.org/cgi/pt?id=uva.x002457945;view=1up;seq=518|trans-title=On phloretin|doi=10.1002/jlac.18550960115}} On p. 120, Hlasiwetz named phloroglucin: ''"Die auffallendste 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 .)</ref><ref>Thorpe, Edward, ed., ''A Dictionary of Applied Chemistry'' (London, England: Longmans, Green, and Co., 1913), vol. 4, </ref>
			A modern synthesis of phloroglucinol involves hydrolysis of benzene-1,3,5-triamine and its derivatives.<ref>{{cite journal|title=Phloroglucinol |author=H. T. Clarke and W. W. Hartman|journal=Org. Synth.|year=1929|volume=9|page=74|doi=10.15227/orgsyn.009.0074}}</ref> Representative is the following route from ].<ref name=Ullmann>{{Cite book | last1 = Fiege | first1 = H. | last2 = Voges | first2 = H. W. | last3 = Hamamoto | first3 = T. | last4 = Umemura | first4 = S. | last5 = Iwata | first5 = T. | last6 = Miki | first6 = H. | last7 = Fujita | first7 = Y. | last8 = Buysch | first8 = H. J. | last9 = Garbe | first9 = D. | last10 = Paulus | doi = 10.1002/14356007.a19_313 | first10 = W. | chapter = Phenol Derivatives | title = Ullmann's Encyclopedia of Industrial Chemistry | year = 2000 | isbn = 978-3527306732 | url = https://books.google.com/books?id=IY-YtwEACAAJ }}</ref>
	]
			:]
			The synthesis is noteworthy because ordinary ] derivatives are unreactive toward ]. Because the triaminobenzene also exists as its ] tautomer, it is susceptible to ].
			== Reactions==
	From water, phloroglucinol crystallizes as the dihydrate, which has a melting point of 116-117 °C, but the anhydrous form melts much higher, at 218-220 °C. It does not boil intact, but it does sublime.
			===Tautomerism and acid-base behavior===
			Phloroglucinol is a weak triprotic acid. The first two pK<sub>a</sub>'s are 8.5 and 8.9.
			As an ], phloroglucinol in principle exists in equilibrium with keto ]s. Evidence for this equilibrium is provided by the formation of the ]:
	==Isolation, synthesis, and reactions==
			:C<sub>6</sub>H<sub>3</sub>(OH)<sub>3</sub> + 3 NH<sub>2</sub>OH → (CH<sub>2</sub>)<sub>3</sub>(C=NOH)<sub>3</sub> + 3 H<sub>2</sub>O
	Phloroglucinol was originally isolated from bark of fruit trees. It is synthesized via a number of processes, but representative is the following route from ]:<ref name=Ullmann>Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Wienheim, 2005. DOI: 10.1002/14356007.a19_313. Published online: 15 June 2002.</ref>
			But it behaves also like a benzenetriol as the three hydroxyl groups can be methylated to give 1,3,5-trimethoxybenzene.<ref name=Ullmann/>
	:]
	The synthesis is noteworthy because ordinary ] derivatives are unreactive toward ]. Because the triaminobenzene also exists as its ] tautomer, it is susceptible to ].
			For the neutral compound, the keto tautomers are undetectable spectroscopically. Upon deprotonation, the keto tautomer predominates.<ref>{{cite journal|title=Dissociation and Keto-Enol Tautomerism of Phloroglucinol and its Anions in Aqueous Solution|author=Martin Lohrie |author2=Wilhelm Knoche|journal=J. Am. Chem. Soc.|year=1993|volume=115|issue=3 |pages=3919–924|doi=10.1021/ja00056a016|bibcode=1993JAChS.115..919L }}</ref>
	The compound behaves like a ketone in its reaction with ], forming the tris(]). But it behaves also like a benzenetriol (''K''<sub>a1</sub> = 3.56 × 10<sup>−9</sup>, ''K''<sub>a2</sub> 1.32×10<sup>−9</sup>), as the three hydroxyl groups can be methylated to give 1,3,5-trimethoxybenzene.<ref name=Ullmann/>
	==Natural occurrence==		===Other reactions===
			From water, phloroglucinol crystallizes as the dihydrate, which has a melting point of 116–117&nbsp;°C, but the anhydrous form melts at a much higher temperature, at 218–220&nbsp;°C. It does not boil intact, but it does sublime.
	Phloroglucinols occur naturally in certain plant species. For example, they (and sometimes their ] dervatives) are present in the fronds of the coastal woodfern, '']''.<ref>C. Michael Hogan. 2008. </ref> ] also produce phloroglucinol derivatives<ref></ref><ref></ref> known as ]s.<ref></ref>
			The ] allows the synthesis of ] from phloroglucinol.<ref>{{cite journal|last1=Gulati|first1=K. C.|last2=Seth|first2=S. R.|last3=Venkataraman|first3=K.|title=Phloroacetophenone|journal=Organic Syntheses|date=1935|volume=15|page=70|doi=10.15227/orgsyn.015.0070}}</ref>
			] can be synthesized from phloroglucinol by a reaction with ] in the presence of a zinc chloride catalyst.
			], described in 1988 by ] and others, can be obtained by ] of 1,3,5-cyclohexanetrione (phloroglucin).<ref name="maier">{{cite journal | title = C<sub>5</sub>O<sub>2</sub> (1,2,3,4-Pentatetraene-1,5-dione), a New Oxide of Carbon |author1=Maier, G. |author2=Reisenauer, H. P. |author3=Schäfer, U. |author4=Balli, H. | journal = Angewandte Chemie International Edition | year = 1988 | volume = 27 | issue = 4 | pages = 566–568 | doi = 10.1002/anie.198805661 }}</ref>
			Phloroglucinol readily forms 5-aminoresorcinol (aka Phloramine) in aqueous ammonia at low temperatures.<ref>{{cite book|last1=Gmelin|first1=Leopold|editor1-last=Watts|editor1-first=Henry|title=Hand-Book of Chemistry, Volume 15|date=1862|publisher=The Cavendish Society|location=London|edition=1st|url=https://books.google.com/books?id=svM4AAAAMAAJ&pg=PA70|access-date=26 December 2016}}</ref><ref name=Treatise />
			Reaction of phloroglucinol and ] gives 30% yield of ]{{cn|date=December 2021}}.
			== Natural occurrences ==
			Phloroglucinol is also generally found in the ] ring A substitution pattern. Indeed, it was originally prepared from ], a compound isolated from fruit trees, using ].<ref name=Treatise>{{cite book|last1=Roscoe|first1=H.E.|last2=Schorlemmer|first2=C.|title=A Treatise on Chemistry, Volume 3, Part 3|date=1893|publisher=D Appleton and Company|location=New York|pages=193 & 253|edition=1st|url=https://books.google.com/books?id=LaM_AAAAYAAJ&pg=PA253|access-date=26 December 2016}}</ref> Additionally, the compound can be similarly prepared from ], plant extracts and ] such as ], ] and ].
			Phloroglucinols are ]s that occur naturally in certain plant species. It is also produced by brown algae and bacteria.
			] derivatives are present in the fronds of the coastal woodfern, '']''<ref>{{cite web|author=C. Michael Hogan|date=December 14, 2008|url=http://www.globaltwitcher.com/artspec_information.asp?thingid=88976 |title=Coastal Woodfern (''Dryopteris arguta'')|website=GlobalTwitcher|url-status=usurped|archive-url=https://web.archive.org/web/20110711102430/http://www.globaltwitcher.com/artspec_information.asp?thingid=88976|archive-date=2011-07-11}}</ref> or in '']''.<ref name=Na>{{Cite journal
			| last1 = Na | first1 = M.
			| last2 = Jang | first2 = J.
			| last3 = Min | first3 = B. S.
			| last4 = Lee | first4 = S. J.
			| last5 = Lee | first5 = M. S.
			| last6 = Kim | first6 = B. Y.
			| last7 = Oh | first7 = W. K.
			| last8 = Ahn | first8 = J. S.
			| doi = 10.1016/j.bmcl.2006.07.018
			| title = Fatty acid synthase inhibitory activity of acylphloroglucinols isolated from Dryopteris crassirhizoma
			| journal = Bioorganic & Medicinal Chemistry Letters
			| volume = 16
			| issue = 18
			| pages = 4738–4742
			| year = 2006
			| pmid = 16870425
			}}</ref> The anthelmintic activity of the root of '']'' has been claimed to be due to ], a phloroglucinol derivative.
			] phloroglucinol compounds (]s, ]s and ]s) can be found in '']'' species.<ref>{{Cite journal
			| doi = 10.1016/S0305-1978(99)00123-4
			| last1 = Eschler | first1 = B. M.
			| last2 = Pass | first2 = D. M.
			| last3 = Willis | first3 = R.
			| last4 = Foley | first4 = W. J.
			| title = Distribution of foliar formylated phloroglucinol derivatives amongst Eucalyptus species
			| journal = Biochemical Systematics and Ecology
			| volume = 28
			| issue = 9
			| pages = 813–824
			| year = 2000
			| pmid = 10913843
			| bibcode = 2000BioSE..28..813E }}</ref> ] and ] are two phloroglucinols found in ]. ] is a phloroglucinol derivative with three ] 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 ('']'').
			]e, such as '']'', '']''<ref>{{Cite journal | last1 = Okada | first1 = Y. | last2 = Ishimaru | first2 = A. | last3 = Suzuki | first3 = R. | last4 = Okuyama | first4 = T. | title = A New Phloroglucinol Derivative from the Brown AlgaEisenia bicyclis: Potential for the Effective Treatment of Diabetic Complications | doi = 10.1021/np030323j | journal = Journal of Natural Products | volume = 67 | issue = 1 | pages = 103–105 | year = 2004 | pmid = 14738398}}</ref> or species in the genus '']'',<ref>{{Cite journal | last1 = Blackman | first1 = A. J. | last2 = Rogers | first2 = G. I. | last3 = Volkman | first3 = J. K. | title = Phloroglucinol Derivatives from Three Australian Marine Algae of the Genus Zonaria | doi = 10.1021/np50055a027 | journal = Journal of Natural Products | volume = 51 | pages = 158–160 | year = 1988 }}</ref> produce phloroglucinol and phloroglucinol derivatives. Brown algae also produce a type of tannins known as ]s.<ref>{{Cite journal | last1 = Shibata | first1 = T. | last2 = Kawaguchi | first2 = S. | last3 = Hama | first3 = Y. | last4 = Inagaki | first4 = M. | last5 = Yamaguchi | first5 = K. | last6 = Nakamura | first6 = T. | doi = 10.1023/B:JAPH.0000047781.24993.0a | title = Local and chemical distribution of phlorotannins in brown algae | journal = Journal of Applied Phycology | volume = 16 | issue = 4 | pages = 291 | year = 2004 | bibcode = 2004JAPco..16..291S | s2cid = 13479924 }}</ref>
			The bacterium '']'' produces phloroglucinol, ] and ].<ref name=Achkar>{{Cite journal | last1 = Achkar | first1 = J. | last2 = Xian | first2 = M. | last3 = Zhao | first3 = H. | last4 = Frost | first4 = J. W. | title = Biosynthesis of Phloroglucinol | doi = 10.1021/ja042340g | journal = Journal of the American Chemical Society | volume = 127 | issue = 15 | pages = 5332–5333 | year = 2005 | pmid = 15826166| bibcode = 2005JAChS.127.5332A }}</ref>
			== Biosynthesis ==
			].]]
			In '']'', biosynthesis of phloroglucinol is performed with a ]. The synthesis begins with the condensation of three ]s. Then decarboxylation followed by the cyclization of the activated ] product leads to the formation of phloroglucinol.<ref name=Achkar/>
			The enzyme ] uses ] and ] (pyrogallol) to produce 1,3,5-trihydroxybenzene (phloroglucinol) and ]. It is found in the bacterium species '']''.
			The enzyme ] uses ] and NADP<sup>+</sup> to produce phloroglucinol, NADPH, and H<sup>+</sup>. It is found in the bacterium species '']''.
			The legume-root nodulating, microsymbiotic nitrogen-fixing bacterium species '']'' is able to degrade ] with formation of ], further decarboxylated to phloroglucinol, which is dehydroxylated to ] and ].
	==Metabolism==
	] uses ] and water to produce ] and phloroglucinol.		] uses ] and water to produce ] and phloroglucinol.
			== Health effects ==
	==Applications==
	Phloroglucinol is mainly used as a coupling agent in printing. It links ]s to give a fast black.
			In some countries and in veterinary medicine, phloroglucinol is used as a treatment for ]s, ] and other related gastrointestinal disorders <ref>{{cite web | title=Phloroglucinol Summary Report | publisher=EMEA | url=http://www.emea.europa.eu/pdfs/vet/mrls/004695en.pdf | access-date=24 April 2009 | url-status=dead | archive-url=https://web.archive.org/web/20070710215947/http://www.emea.europa.eu/pdfs/vet/mrls/004695en.pdf | archive-date=10 July 2007 }}</ref>
	It is useful for the industrial synthesis of pharmaceuticals<ref>{{cite web | title=Intermediate Pharmaceutical Ingredients - Flopropione | publisher=Univar Canada | url=http://www.univarcanada.com/pdfdoc/pharmaceutical/Intermediates.pdf | accessdate=24 April 2009 }}</ref> and explosives.<ref>{{cite web | year=1984 | title=Synthesis of trinitrophloroglucinol | publisher=The United States Patent and Trademark Office | url=http://www.freepatentsonline.com/4434304.html | accessdate=24 April 2009 }}</ref> It is also used as a treatment for gallstones, spasmodic pain and other related gastrointestinal disorders.<ref>{{cite web | year=1999 | title=PHLOROGLUCINOL | publisher=Biam | url=http://www.biam2.org/www/Sub2438.html | accessdate=24 April 2009 }} (in French)</ref><ref>{{cite web | title=Phloroglucinol Summary Report | publisher=EMEA | url=http://www.emea.europa.eu/pdfs/vet/mrls/004695en.pdf | accessdate=24 April 2009 }}</ref><ref>{{cite journal | author=Chassany O et al. | title=Acute exacerbation of pain in irritable bowel syndrome: efficacy of phloroglucinol/trimethylphloroglucinol. A randomized, double-blind, placebo-controlled study. | journal=Alimentary pharmacology & therapeutics | volume=1 | issue=25 | year=2007 | pages=1115–23}} {{PMID|17439513}}</ref> 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.
			A 2018 review found insufficient evidence that phloroglucinol was effective for treating abdominal pain <ref name="pmid29350249">{{cite journal | vauthors =Blanchard, C, Pouchain, D, Vanderkam, P, Perault-Pochat, M, Boussageon, R, Vaillant-Roussel, H| title =Efficacy of phloroglucinol for treatment of abdominal pain: a systematic review of literature and meta-analysis of randomised controlled trials versus placebo. | journal =Eur J Clin Pharmacol| date = 2018 | volume =74 | issue =5 | pages =541–548 | doi= 10.1007/s00228-018-2416-6| pmid =29350249 | s2cid =4700542 }}</ref>
			A 2020 review found insufficient evidence that phloroglucinol was effective for treating pain caused by ] and ] conditions.<ref name="pmid31435708">{{cite journal | vauthors =Clara B, Paul V, Denis P, Stéphanie M, Hélène VR, Rémy B| title =Efficacy of phloroglucinol for the treatment of pain of gynaecologic or obstetrical origin: a systematic review of literature of randomised controlled trials. | journal =Eur J Clin Pharmacol| date = 2020 | volume =76 | issue =1 | pages =1–6 | doi= 10.1007/s00228-019-02745-7| pmid =31435708 | s2cid =201103441 }}</ref> A 2022 phase 3 study conducted in Italy on 364 patients indicated phloroglucinol and its derivative must be as effective as ] for the treatment of pain and spasms of biliary or urinary tracts.<ref>{{Cite journal |last1=Corvino |first1=Angela |last2=Magli |first2=Elisa |last3=Minale |first3=Massimiliano |last4=Autelitano |first4=Andrea |last5=Valente |first5=Valeria |last6=Pierantoni |first6=Giovanna Maria |date=2023-02-01 |title=Phloroglucinol-Derived Medications are Effective in Reducing Pain and Spasms of Urinary and Biliary Tracts: Results of Phase 3 Multicentre, Open-Label, Randomized, Comparative Studies of Clinical Effectiveness and Safety |url=https://doi.org/10.1007/s12325-022-02347-3 |journal=Advances in Therapy |language=en |volume=40 |issue=2 |pages=619–640 |doi=10.1007/s12325-022-02347-3 |issn=1865-8652 |pmc=9898402 |pmid=36443585}}</ref>
			Phloroglucinols acylated derivatives have a ] inhibitory activity.<ref name=Na/>
	Phloroglucinolysis is an analytical technique to study ]s by mean of ]. The reaction makes use of phloroglucinol as ].
			=== ATC classification===
	==References==
			It has the A03AX12 code in the A03AX ''Other drugs for functional bowel disorders'' section of the ] '' Drugs for functional gastrointestinal disorders'' subgroup of the Anatomical Therapeutic Chemical Classification System. It also has the D02.755.684 code in the ] ''Organic chemicals'' section of the Medical Subject Headings (MeSH) codes by the United States National Library of Medicine.
	<references/>
			== Applications ==
			Phloroglucinol is mainly used as a coupling agent in printing. It links ]s to give a fast black.
			It is useful for the industrial synthesis of pharmaceuticals (]<ref>{{cite web | title=Intermediate Pharmaceutical Ingredients - Flopropione | publisher=Univar Canada | url=http://www.univarcanada.com/pdfdoc/pharmaceutical/Intermediates.pdf | access-date=24 April 2009 }}</ref>), ], and explosives (] (2,4,6-triamino-1,3,5-trinitrobenzene), ],<ref>{{cite web | year=1984 | title=Synthesis of trinitrophloroglucinol | publisher=The United States Patent and Trademark Office | url=http://www.freepatentsonline.com/4434304.html | access-date=24 April 2009 }}</ref> ]<ref>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}}</ref>).
			Phloroglucinolysis is an analytical technique to study ]s by means of ]. The reaction makes use of phloroglucinol as ]. ]s formation (tannins condensation and precipitation) can be minimized in using strong nucleophiles, such as phloroglucinol, during pine tannins extraction.<ref>{{Cite journal | last1 = Sealy-Fisher | first1 = V. J. | last2 = Pizzi | first2 = A. | doi = 10.1007/BF02663290 | title = Increased pine tannins extraction and wood adhesives development by phlobaphenes minimization | journal = Holz Als Roh- und Werkstoff | volume = 50 | issue = 5 | pages = 212 | year = 1992 | s2cid = 6585979 }}</ref>
			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.<ref>{{Cite journal|last1=Teixeira da Silva|first1=Jaime A.|last2=Dobránszki|first2=Judit|last3=Ross|first3=Silvia|date=2013-02-01|title=Phloroglucinol in plant tissue culture|journal=In Vitro Cellular & Developmental Biology - Plant|language=en|volume=49|issue=1|pages=1–16|doi=10.1007/s11627-013-9491-2|s2cid=15470904|issn=1475-2689}}</ref>
			=== Use in tests ===
			Phloroglucinol is a reagent of the ]' test for ]s. This test relies on reaction of the ] with phloroglucinol to produce a colored compound with high molar absorptivity.<ref>Oshitna, K., and Tollens, B., Ueber Spectral-reactionen des Methylfurfurols. Ber. Dtsch. Chem. Ges. 34, 1425 (1901)</ref>
			A solution of hydrochloric acid and phloroglucinol is also used for the detection of ] (Wiesner test). A brilliant red color develops, owing to the presence of ] groups in the lignin.<ref>Lignin production and detection in wood. John M. Harkin, U.S. Forest Service Research Note FPL-0148, November 1966 ( {{Webarchive|url=https://web.archive.org/web/20200305091429/http://www.fpl.fs.fed.us/documnts/fplrn/fplrn0148.pdf |date=2020-03-05 }})</ref> A similar test can be performed with ].
			It is also part of ], an alcoholic solution of phloroglucinol and ], for the qualitative detection of free hydrochloric acid in gastric juice.
			== References ==
			{{Reflist}}
	{{Drugs for functional gastrointestinal disorders}}		{{Drugs for functional gastrointestinal disorders}}
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