Phloroglucinol

Reaction of formaldehyde with phloroglucinol under alkaline conditions generates orange compound. The colorimetric assay determination of this compound at the maximum absorption wavelength of 460 nm, can be used to detect low or trace formaldehyde in textile and garment.
Since phloroglucinol may occur enol and keto tautomers, it can react with ammonia according following reaction:

Under the influence of ammonia, 1,3,5-Benzenetriamine can be obtained by keto reaction of phloroglucinol, while this amine can also hydrolyze in aqueous acid to generate phloroglucinol. Besides phloroglucinol can also have enol reaction.

The information above is edited by Andy from Chemicalbook.

This product is a white or light yellow crystal or crystalline powder with melting point of 218 ℃. Usually it carries two molecular crystallization water ([6099-90-7]) and converts into anhydrous at 110 ℃. It can be dissolved in 100 parts of water, 10 parts of ethanol, and 0.5 parts of pyridine and is soluble in ether. Besides It partially decomposes when sublimation, and changes its color when exposed to the light. In addition it tastes sweet.

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.

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%.

Category: Toxic substances
Toxicity grade: Moderate toxicity
Acute toxicity: oral-rat LD50: 4000 mg/kg; Oral-Mouse LD50: 4550 mg/kg
Flammability hazard characteristics: Combustible fire burning can cause smoke irritation
Storage characteristics: Ventilated, low-temperature and dry warehouse; and separately with oxidants
Extinguishing agents: Carbon dioxide, foam, sand and water mist

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.

white to light yellow crystal

Phloroglucinol crystallizes in the anhydrous form or as the dihydrate. Recrystallization from water gives the dihydrate, which is colorless, oderless, sweet in taste, and forms rhombic crystals. The dihydrate is converted into the anhydrous form by heating at 110 ℃. Phloroglucinol sublimes at higher temperatures with partial decomposition.

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.

ChEBI: Phloroglucinol is a benzenetriol with hydroxy groups at position 1, 3 and 5. It has a role as an algal metabolite.

Phloroglucinol (phlo) is a phenol derivative that shows cyctoprotective effect from oxidative damage by enhancing the activity of cellular catalase.
It can react with benzaldehyde derivatives to form phloroglucinol-based microporous polymeric organic frameworks (phlo-POF) with potential applications in ion-exchange and gas adsorption.
Phlo can also be used to prepare synthetic analogs of A-type proanthocyanidins (PACs) such as 2,8-dioxabicyclo[3.3.1]nonane derivatives by reacting with the corresponding flavylium salts.

Phloroglucinol is a trihydroxybenzene with antithrombotic, profibrinolytic, antimicrobial, antimalarial, cancer chemopreventive, anti-HIV and anti-leishmanial activities. Phloroglucinol (PG) is a biosynthetic precursor of the 2,4-diacetylphloroglucinol (DAPG) an antibiotic against soil-borne diseases. Phloroglucinol is a useful intermediate because it is polyfunctional.

Not classified

Moderately toxic by subcutaneous and intraperitoneal routes. Mildly toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. Used in diazo-type printing and textile dyeing, in microscopy as a bone specimen decalcifier

Crystallise the triol from water, and store it in the dark under nitrogen. [Beilstein 6 IV 7361.]

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