ChemicalBook CAS DataBase List 108-73-6

108-73-6

Name	Phloroglucinol
CAS	108-73-6
EINECS(EC#)	203-611-2
Molecular Formula	C6H6O3
MDL Number	MFCD00002286
Molecular Weight	126.11
MOL File	108-73-6.mol

Synonyms

1,2,5-TRIHYDROXYBENZENE 1,3,5-BENZENETRIOL 1,3,5-THB 1,3,5-TRIHYDROXYBENZENE 1,3,5-TRIHYDROXYBENZENE ANH 3,5-DIHYDROXYPHENOL 5-HYDROXYRESORCINOL AKOS BBS-00004257 PHLOROGLUCIN PHLOROGLUCINOL PHLOROGLUCINOL TS TRIHYDROXYBENZENE ?hloroglucin 1,3,5-trihydroxy-benzen 1,3,5-Trihydroxycyclohexatriene 5-Oxyresorcinol 5-Oxyresorcinolphloroglucin Benzene, 1,3,5-trihydroxy- Benzene, trihydroxy benzene,trihydroxy

Chemical Properties

Appearance	white to light yellow crystal
Melting point	215-220 °C
Boiling point	194.21°C (rough estimate)
bulk density	560kg/m3
density	0.801 g/mL at 20 °C
vapor pressure	0.001Pa at 25℃
refractive index	n20/D 1.365
Fp	14 °C
storage temp.	Dark Room
solubility	Soluble in diethyl ether, ethanol and pyridine.
form	Crystalline Powder
pka	pK1:8.45(0);pK2:8.88(-1) (25°C)
color	White to light beige
Water Solubility	11.17g/L(room temperature)
Sensitive	Light Sensitive & Hygroscopic
Merck	14,7328
BRN	1341907
Cosmetics Ingredients Functions	HAIR DYEING
InChI	1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
InChIKey	QCDYQQDYXPDABM-UHFFFAOYSA-N
SMILES	Oc1cc(O)cc(O)c1
LogP	0.55 at 25℃
CAS DataBase Reference	108-73-6(CAS DataBase Reference)
NIST Chemistry Reference	1,3,5-Benzenetriol(108-73-6)
EPA Substance Registry System	1,3,5-Benzenetriol (108-73-6)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H315-H317-H319-H335
Precautionary statements	P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes	F,Xi
Risk Statements	R11:Highly Flammable. R36/37/38:Irritating to eyes, respiratory system and skin . R34:Causes burns. less more
Safety Statements	S7:Keep container tightly closed . S16:Keep away from sources of ignition-No smoking . S24/25:Avoid contact with skin and eyes . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . less more
RIDADR	UN 1170 3/PG 2
WGK Germany	2
RTECS	SY1050000
TSCA	Yes
REACH Registrations	Active
HS Code	29072900
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3
Safety Profile	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 less more
Toxicity	LD50 in mice, rats (g/kg): 4.7, 4.0 i.g. (Cahen) less more

Raw materials And Preparation Products

Hazard Information

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.

Physical properties

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.

Application

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.

Definition

ChEBI: A benzenetriol with hydroxy groups at position 1, 3 and 5.

General Description

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.

Flammability and Explosibility

Notclassified

storage

Store at RT

Purification Methods

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

References

[1] JIHANE ACHKAR. Biosynthesis of Phloroglucinol[J]. Journal of the American Chemical Society, 2005, 127 15: 5332-5333. DOI: 10.1021/ja042340g
[2] KYOUNG AH KANG. Cytoprotective effect of phloroglucinol on oxidative stress induced cell damage via catalase activation[J]. Journal of cellular biochemistry, 2005, 97 3: 609-620. DOI: 10.1002/jcb.20668
[3] MI-HYE KANG Taek J N In Hye Kim. Phloroglucinol induces apoptosis through the regulation of insulin-like growth factor 1 receptor signaling pathways in human colon cancer HT-29 cells.[J]. International journal of oncology, 2014, 45 3: 1036-1042. DOI: 10.3892/ijo.2014.2521
[4] RAE-KWON KIM. Phloroglucinol suppresses metastatic ability of breast cancer cells by inhibition of epithelial-mesenchymal cell transition[J]. Cancer Science, 2014, 106 1: 94-101. DOI: 10.1111/cas.12562
[5] EUN-JEONG YANG. Phloroglucinol Attenuates the Cognitive Deficits of the 5XFAD Mouse Model of Alzheimer’s Disease.[J]. ACS Applied Bio Materials, 2015: e0135686. DOI: 10.1371/journal.pone.0135686
[6] JANA KHOLOVá. Component traits of plant water use are modulated by vapour pressure deficit in pearl millet (Pennisetum glaucum (L.) R.Br.).[J]. Functional Plant Biology, 2016, 43 5: 423-437. DOI: 10.1071/fp15115
[7] MARIA B. CAVALCANTE. Reactive Oxygen Species and Cellular Interactions Between Mycosphaerella fijiensis and Banana[J]. Tropical Plant Biology, 2011, 4 1: 134-143. DOI: 10.1007/s12042-011-9071-8
[8] SINGH I P, SIDANA J, BHARATE S B, et al. Phloroglucinol compounds of natural origin: Synthetic aspects[J]. Natural Product Reports, 2010, 3: 393-416. DOI: 10.1039/b914364p
[9] INOUE S. EFFECTS OF 1,3,5-TRIHYDROXYBENZENE AND 2,4,6-TRIHYDROXY-1-PROPIOPHENONE ON THE SMOOTH MUSCLE ORGANS[J]. Japanese journal of pharmacology, 1969, 19 2: Pages 224-233. DOI: 10.1254/jjp.19.224
[10] O. CHASSANY. Acute exacerbation of pain in irritable bowel syndrome: efficacy of phloroglucinol/trimethylphloroglucinol – a randomized, double-blind, placebo-controlled study[J]. Alimentary Pharmacology & Therapeutics, 2007, 25 9: 1115-1123. DOI: 10.1111/j.1365-2036.2007.03296.x
[11] SAMIA TABASSUM. Phloroglucinol for acceleration of labour: double blind, randomized controlled trial.[J]. Journal of the Pakistan Medical Association, 2005, 55 7: 270-273.

Material Safety Data Sheet(MSDS)

Questions And Answer

Feature reaction of 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.;
Chemical properties
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.;
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.;
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%.;
Hazards & Safety Information
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;

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108-73-6

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Preparation Products

Hazard Information

Description

Physical properties

Application

Definition

General Description

Flammability and Explosibility

storage

Purification Methods

References

Material Safety Data Sheet(MSDS)

Questions And Answer

Feature reaction of phloroglucinol

Chemical properties

Uses

Production method

Hazards & Safety Information

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

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