Phloroglucinol

Base Information

• Chemical Name: Phloroglucinol
• CAS No.: 108-73-6
• Molecular Formula: C6H6O3
• Molecular Weight: 126.112
• Hs Code.: 2907.29
• European Community (EC) Number: 203-611-2
• NSC Number: 1572
• UNII: DHD7FFG6YS
• DSSTox Substance ID: DTXSID9048354
• Nikkaji Number: J2.866E
• Wikipedia: Phloroglucinol
• Wikidata: Q899008
• Metabolomics Workbench ID: 42470
• ChEMBL ID: CHEMBL473159
• Mol file: 108-73-6.mol

Synonyms:5-Oxyresorcinolphloroglucin;1,3,5-Trihydroxycyclohexatriene;Benzene, trihydroxy;s-Trihydroxybenzene;4-06-00-07361 (Beilstein Handbook Reference);Spasfon-Lyoc;See also 1,3,5-Benzenetriol;Benzene-s-triol;Benzene-1,3,5-triol;sym-Trihydroxybenzene;1,3, 5-Trihydroxybenzene;1,3,5-benzenetriol;Dilospan S;1,3,5-Trihydroxybenzene;1,3,5-THB;Floroglucin [Czech];1.3.5-Trihydroxybenzene;5-Oxyresorcinol;Floroglucinol [Czech];5-Hydroxyresorcinol;5-Benzenetriol;Benzene, 1,3,5-trihydroxy-;1,3,5-Triol;3,5-Dihydroxyphenol;1,3,5-Trihydroxybenzene anhydrate;Phloroglucinol Anhydrous;m-Trihydroxybenzene;Phloroglucinol Dihydrate;1,3,5-trihydroxy benzene;

Chemical Property of Phloroglucinol

Chemical Property:

• Appearance/Colour: white to light yellow crystal
• Vapor Pressure: 8.27E-05mmHg at 25°C
• Melting Point: 215-220 °C
• Refractive Index: n20/D 1.365
• Boiling Point: 331.1 °C at 760 mmHg
• PKA: pK1:8.45(0);pK2:8.88(-1) (25°C)
• Flash Point: 174.9 °C
• PSA: 60.69000
• Density: 1.488 g/cm³
• LogP: 0.80340
• Storage Temp.: Dark Room
• Sensitive.: Light Sensitive & Hygroscopic
• Solubility.: Soluble in diethyl ether, ethanol and pyridine.
• Water Solubility.: 11.17g/L(room temperature)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 126.031694049
• Heavy Atom Count: 9
• Complexity: 63.3

Purity/Quality:

99% ^*data from raw suppliers

Phloroglucinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38-34-43
• Safety Statements: 7-16-24/25-45-36/37/39-26-36/37-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: C1=C(C=C(C=C1O)O)O
• Recent ClinicalTrials: Effect of Oral Phloroglucin (Flospan?) as Premedication of Non-sedative Diagnostic Esophagogastroduodenoscopy
• Uses: Phloroglucinol can be used in verifications of antimony, arsenic, cerium, chromate, chromium, gold, iron, mercury, nitrites, osmium, palladium, tin, vanadium, vanillin and lignin, and measurement of furfural, pentose, pentosan, methanol, chloral hydrate, turpentine, Lignified cell tissues, free acid in gastric juice (HCl) and decalcified bone specimens. Besides it can also be used as biological reagent dyes. Phloroglucinol is mainly used as a coupling agent in printing. It is an active component of Tollen's reagent and Gunzburg reagent used to test pentoses and hydrochloric acid in gastric juice respectively. In analytical chemistry, it is used to study condensed tannins by means of depolymerization. It is also involved in the synthesis of 2,4,6-triamino-1,3,5- trinitrobenzene, trinitrophloroglucinol and pharmaceuticals like flopropione. Phloroglucinol (1,3,5-trihydroxybenzene) is the core structure of a large family of substituted phenolics with broad, albeit weak, biological activity. Phloroglucinol is a useful metabolite for HPLC/DAD and bioassay dereplication.diagnostic aid growth hormone releasing factor. Antispasmodic.
• Production method: 2,4,6-aminobenzoic acid can be obtained by 2,4,6-trinitrobenzoic acid`s reduction of zinc particles. After its dilute solution was heated at reflux for 20h, acidified with hydrochloric acid, cooled and crystallized, phloroglucinol can be obtained with a yield of 46-53%.
• Description: Phloroglucinol is a naturally occurring phenol that exhibits diverse biological activities. Phloroglucinol protects V79-4 Chinese hamster lung fibroblast cells from oxidative stress and inhibits lipid peroxidation by scavenging reactive oxygen species (ROS). It induces apoptosis in HT-29 human colon cancer cells and inhibits metastasis of BT549 and MDA-MB-231 human breast cancer cells. Phloroglucinol protects primary neurons from β-amyloid-induced dendritic spine loss in vitro and shortens the latency to find the platform in a Morris water maze test in an Alzheimer’s disease (AD) mouse model. Phloroglucinol has been used to stain histological plant sections and in the synthesis of numerous natural products. Phloroglucinol slows the frequency and decreases the amplitude of contraction in isolated rabbit and rat intestine at a concentration of 100 and 1 μM, respectively. Formulations containing phloroglucinol have been used as antispasmodics.

Technology Process of Phloroglucinol

There total 228 articles about Phloroglucinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

2,4-diacetylphloroglucinol (2161-86-6) + recorcinol (108-46-3) → 2',4'-dihydroxy-4-acetophenone (89-84-9) + 3,5-dihydroxyphenol (108-73-6)

Guidance literature:

With cell-free E_. coli extract containing the recombinant acyltransferase from Pseudomonas protegens; In aq. phosphate buffer; dimethyl sulfoxide; at 35 ℃; for 0.5h; pH=7.5; Solvent; pH-value; Temperature; Catalytic behavior; Enzymatic reaction;

DOI:10.1007/s00253-018-9052-z

Reference yield: 13.0%

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) + recorcinol (108-46-3) → 2',4'-dihydroxy-4-acetophenone (89-84-9) + 3,5-dihydroxyphenol (108-73-6)

Guidance literature:

With cell-free E_. coli extract containing the recombinant acyltransferase from Pseudomonas protegens; In aq. phosphate buffer; dimethyl sulfoxide; at 35 ℃; for 0.5h; pH=7.5; Enzymatic reaction;

DOI:10.1007/s00253-018-9052-z

Reference yield:

5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one (480-43-3,26207-61-4,65337-52-2) → 3,5-dihydroxyphenol (108-73-6) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

bei der Kalischmelze;

upstream raw materials:

orcinol

1,3,5-trinitrobenzene

2,4,6-Trinitrotoluene

1,2,3-trimethoxybenzene

Downstream raw materials:

1,2,3-trimethoxybenzene

2,4,6-tris-morpholinomethyl-phloroglucinol

5,7-dihydroxy-3,4-dimethylcoumarin

1,3,5-triacetoxybenzene

Refernces

• 1、 Ceshire et al.. "". . p. 5155,5156,5157,5159,5163. Retrieved 1968.
• 2、 Tilden. "". . p. 344. Retrieved 1892.
• 3、 Hayashi, Asuka,Saitou, Hiroki,Mori, Tomomi,Matano, Ikue,Sugisaki, Hiroyuki,Maruyama, Kiyofumi. "Molecular and catalytic properties of monoacetylphloroglucinol acetyltransferase from pseudomonas sp. YGJ3". . p. 559 - 566. Retrieved 2012.
• 4、 Alaniya,Kavtaradze,Skhirtladze. "Anthocyan glycoside from Hedera colchica". . p. 673 - 674. Retrieved 2008.
• 5、 Chauhan, J. S.,Kumar, Santosh,Chaturvedi, Rajesh. "A FLAVONE GLYCOSIDE FROM THE STEM OF IXORA ARBOREA". . p. 2404 - 2405. Retrieved 1984.
• 6、 Hazura,Benedikt. "". . p. 702. Retrieved 1885.
• 7、 Ghosal,Dutta. "". . p. 195,197. Retrieved 1971.
• 8、 Abdullazhanova,Mavlyanov,Abdullaev. "Phenolic compounds from Oenothera gigas". . p. 97 - 98. Retrieved 2000.
• 9、 Tilden,Beck. "". . p. 323. Retrieved 1890.
• 10、 Carrillo, Romen,Daranas, Antonio Hernández,Martín-Encinas, Endika,Pérez-Pérez, Yaiza,Pasán, Jorge,Rivero, David S.,Santos, Tanausú. "Dynamic Nucleophilic Aromatic Substitution of Tetrazines". . p. 18783 - 18791. Retrieved 2021/07/20.