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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:
1341907
EC Number:
203-611-2
MDL number:
MFCD00002286
UNSPSC Code:
12352100
PubChem Substance ID:
57652786
NACRES:
NA.22
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Quality Level

200

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.[1]
  • 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.[2]
  • 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.[3]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM5781
BCCK5832
BCCG9733
BCCF3066
BCCB9746

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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)
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.
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)
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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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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