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P3502

Sigma-Aldrich

Phloroglucinol

Used to detect the presence of wood fiber.

Synonym(s):

1,3,5-Trihydroxybenzene

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About This Item

Empirical Formula (Hill Notation):
C6H6O3
CAS Number:
Molecular Weight:
126.11
Beilstein/REAXYS Number:
1341907
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

Quality Level

form

powder or crystals

mp

215-220 °C

solubility

ethanol: 50 mg/mL (clear to hazy)

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Oc1cc(O)cc(O)c1

InChI

1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H

InChI key

QCDYQQDYXPDABM-UHFFFAOYSA-N

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General description

Phloroglucinol (phlo) is a phenol derivative that shows a cytoprotective effect from oxidative damage by enhancing the activity of cellular catalase. It 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. Phlo can react with benzaldehyde derivatives to form phloroglucinol-based microporous polymeric organic frameworks (phlo-POF) with potential applications in ion exchange and gas adsorption.
Phloroglucinol is an antispasmodic and a derivative of phenol.

Application

Phloroglucinol has been used to prevent hyperhydricity by promoting the lignification of shoots. It has also been used in PG (phloroglucinol)-sucrose treatments for the growth and development of in vitro derived shoot tips. Phloroglucinol has been used to stain root sections. It has also been used to stain plant sections to identify plant materials like lignin.
Phloroglucinol has been used to stain root sections. It has also been used to stain plant sections to identify plant materials like lignin.

Biochem/physiol Actions

Phloroglucinol displays antispasmodic activity. It 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.

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Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Reactive Oxygen Species and Cellular Interactions
Between Mycosphaerella fijiensis and Banana
Maria
Tropical Plant Biology (2011)
Role of antispasmodics in the treatment of irritable bowel syndrome
Anita Annahazi
World Journal of Gastrointestinal Oncology (2014)
Component traits of plant water use are modulated by vapour
pressure deficit in pearl millet (Pennisetum glaucum (L.) R.Br.)
Jana Kholova
Functional Ecology (2016)
Poplar stems show opposite epigenetic patterns during winter
dormancy and vegetative growth
Daniel Conde
Trees (Berlin, Germany : West) (2013)
Juliana Almario et al.
Molecular plant-microbe interactions : MPMI, 26(5), 566-574 (2013-02-15)
Pseudomonas strains producing 2,4-diacetylphloroglucinol (DAPG) can protect plants from soilborne phytopathogens and are considered the primary reason for suppressiveness of morainic Swiss soils to Thielaviopsis basicola-mediated black root-rot disease of tobacco, even though they also occur nearby in conducive sandstone

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