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79330

Sigma-Aldrich

Phloroglucinol

≥99.0% (HPLC)

Synonym(s):

1,3,5-Trihydroxybenzene

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About This Item

Empirical Formula (Hill Notation):
C6H6O3
CAS Number:
108-73-6
Molecular Weight:
126.11
Beilstein/REAXYS Number:
1341907
EC Number:
203-611-2
MDL number:
MFCD00002286
UNSPSC Code:
12352100
PubChem Substance ID:
57652786
NACRES:
NA.22

assay

≥99.0% (HPLC)

form

solid

impurities

diresorcin, none detected
≤2% water

mp

215-220 °C

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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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.

pictograms

Exclamation mark
GHS07

signalword

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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Thermodynamic Stability of Flavylium Salts as a Valuable Tool To Design the Synthesis of A-Type Proanthocyanidin Analogues
Alejo-Armijo A, et al.
The Journal of Organic Chemistry, 83(19), 12297-12304 (2018)
Claudia Birkemeyer et al.
Metabolites, 10(9) (2020-09-17)
Accumulation of biologically active metabolites is a specific feature of plant biochemistry, directing the use of plants in numerous applications in the pharmaceutical and food industries. Among these substances, the plethora of phenolic compounds has attracted particular interest among researchers.
Efficient and Rapid Photocatalytic Reduction of Hexavalent Chromium Achieved by a Phloroglucinol-Derived Microporous Polymeric Organic Framework Solid
Kostas V, et al.
The Journal of Physical Chemistry C, 121(13), 7303-7311 (2017)
Cytoprotective effect of phloroglucinol on oxidative stress induced cell damage via catalase activation
Kang KA, et al.
Journal of Cellular Biochemistry, 97(3), 609-620 (2006)
Anne M Vissers et al.
Phytochemical analysis : PCA, 28(6), 487-495 (2017-06-15)
Phlorotannins are complex mixtures of phloroglucinol oligomers connected via C-C (fucols) or C-O-C (phlorethols) linkages. Their uniformity in subunits and large molecular weight hamper their structural analysis. Despite its commercial relevance for alginate extraction, phlorotannins in Laminaria digitata have not
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