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Phloroglucinol

Names
IUPAC name Benzene-1,3,5-triol
Other names phloroglucine, 1,3,5-trihydroxybenzene, 1,3,5-benzenetriol, or cyclohexane-1,3,5-trione
Identifiers
CAS Number	108-73-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16204
ChEMBL	ChEMBL473159
ChemSpider	352
ECHA InfoCard	100.003.284
PubChem CID	359
RTECS number	UX1050000
UNII	DHD7FFG6YS
CompTox Dashboard (EPA)	DTXSID9048354
InChI InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9HKey: QCDYQQDYXPDABM-UHFFFAOYSA-N InChI=1/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9HKey: QCDYQQDYXPDABM-UHFFFAOYAF
SMILES c1c(cc(cc1O)O)O
Properties
Chemical formula	C6H6O3
Molar mass	126.11 g/mol
Appearance	white solid
Melting point	218-220 °C
Solubility in water	1 g/100 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Phloroglucinol is a benzenetriol. It is an organic compound that is used in the synthesis of pharmaceuticals and explosives. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5-cyclohexanetrione (phloroglucin), which has ketone-like character. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional.

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.

Isolation, synthesis, and reactions

Phloroglucinol was originally isolated from bark of fruit trees. It is synthesized via a number of processes, but representative is the following route from trinitrobenzene:

File:Phlorosynth.png

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 (K_a1 = 3.56 × 10, K_a2 1.32×10), as the three hydroxyl groups can be methylated to give 1,3,5-trimethoxybenzene.

Natural occurrence

Phloroglucinols occur naturally in certain plant species. For example, they (and sometimes their acyl dervatives) are present in the fronds of the coastal woodfern, Dryopteris arguta. Brown algae also produce phloroglucinol derivatives known as phlorotannins.

Metabolism

Phloretin hydrolase uses phloretin and water to produce phloretate and phloroglucinol.

Applications

Phloroglucinol is mainly used as a coupling agent in printing. It links diazo dyes to give a fast black.

It is useful for the industrial synthesis of pharmaceuticals and explosives. 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.

Phloroglucinolysis is an analytical technique to study condensed tannins by mean of depolymerisation. The reaction makes use of phloroglucinol as nucleophile.

References

1. ^ 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.
2. C. Michael Hogan. 2008. Coastal Woodfern (Dryopteris arguta), GlobalTwitcher, ed. N. Stromberg
3. A New Phloroglucinol Derivative from the Brown Alga Eisenia bicyclis: Potential for the Effective Treatment of Diabetic Complications. Yoshihito Okada, Akiko Ishimaru, Ryuichiro Suzuki and Toru Okuyama, J. Nat. Prod., 2004, 67 (1), pp 103–105, DOI: 10.1021/np030323j
4. Phloroglucinol Derivatives from Three Australian Marine Algae of the Genus Zonaria. Adrian J. Blackman, Glen I. Rogers and John K. Volkman, J. Nat. Prod., 1988, 51 (1), pp 158–160, DOI: 10.1021/np50055a027
5. Local and chemical distribution of phlorotannins in brown algae. Toshiyuki Shibata, Shigeo Kawaguchi, Yoichiro Hama, Masanori Inagaki, Kuniko Yamaguchi and Takashi Nakamura, Journal of Applied Phycology, Volume 16, Number 4, 291-296, DOI: 10.1023/B:JAPH.0000047781.24993.0a
6. "Intermediate Pharmaceutical Ingredients - Flopropione" (PDF). Univar Canada. Retrieved 24 April 2009.
7. "Synthesis of trinitrophloroglucinol". The United States Patent and Trademark Office. 1984. Retrieved 24 April 2009.
8. "PHLOROGLUCINOL". Biam. 1999. Retrieved 24 April 2009. (in French)
9. "Phloroglucinol Summary Report" (PDF). EMEA. Retrieved 24 April 2009.
10. Chassany O; et al. (2007). "Acute exacerbation of pain in irritable bowel syndrome: efficacy of phloroglucinol/trimethylphloroglucinol. A randomized, double-blind, placebo-controlled study". Alimentary pharmacology & therapeutics. 1 (25): 1115–23. {{cite journal}}: Explicit use of et al. in: |author= (help) PMID 17439513

• Phloroglucinols