Phloracetophenone - ≥98% , CAS No.480-66-0

CAS: 480-66-0 Cat. No.: P413178 Molecular Weight: 168.15 Beilstein Registry Number: 1911197 EC Number: 207-556-5 PubChem CID: 68073

GRADE & PURITY ≥98%

Synonyms

BDBM50249070 | 2-Acetylphloroglucinol | CK2566 | NSC 54927 | SCHEMBL105416 | Acetophenone, 2',4',6'-trihydroxy- (8CI) | InChI=1/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H | BRD-K64824948-001-02-2 | Phloracetophenone | 2',6'-Trihydroxyacetophenone

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Phloracetophenone Phloracetophenone, or 2,4,6-trihydroxyacetophenone (THA), the aglycone component of phloracetophenone glucoside, is a naturally occurring compound obtained from the rhizome of Curcuma comosa (Family Zingiberaceae). Phloracetophenone can stimulate CYP7A1 activity. Phloracetophenone induces cholestasis in rats mediated through Mrp2.

Specifications

Synonyms

BDBM50249070 | 2-Acetylphloroglucinol | CK2566 | NSC 54927 | SCHEMBL105416 | Acetophenone, 2', 4', 6'-trihydroxy- (8CI) | InChI=1/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3, 10-12H, 1H | BRD-K64824948-001-02-2 | Phloracetophenone | 2', 6'-Trihydroxyacetophenone

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Phloracetophenone, or 2, 4, 6-trihydroxyacetophenone (THA), the aglycone component of phloracetophenone glucoside, is a naturally occurring compound obtained from the rhizome of Curcuma comosa (Family Zingiberaceae). Phloracetophenone can stimulate CYP7A1 a

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504754245
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754245
• Canonical Smiles: CC(=O)C1=C(C=C(C=C1O)O)O
• IUPAC Name: 1-(2,4,6-trihydroxyphenyl)ethanone
• InChIKey: XLEYFDVVXLMULC-UHFFFAOYSA-N
• INCHI: 1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3
• Isomeric SMILES: CC(=O)C1=C(C=C(C=C1O)O)O
• WGK Germany: 3
• RTECS: AN0528000
• Alternate CAS: 249278-28-2
• PubChem CID: 68073
• Molecular Weight: 168.15
• Beilstein: 1911197
• Reaxy-Rn: 1911197

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones
• Direct Parent: Alkyl-phenylketones
• Alternative Parents: Acylphloroglucinols and derivatives Acetophenones Benzoyl derivatives Aryl alkyl ketones 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Polyols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Acylphloroglucinol derivative - Acetophenone - Phloroglucinol derivative - Benzenetriol - Aryl alkyl ketone - Benzoyl - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Vinylogous acid - Polyol - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
• External Descriptors: methyl ketone - aromatic ketone - benzenetriol

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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LoVo (4724 Activities)

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PC-3 (62116 Activities)

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SK-MEL-28 (48833 Activities)

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U-937 (7138 Activities)

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A549 (127892 Activities)

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MIA PaCa-2 (5949 Activities)

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HCT-116 (91556 Activities)

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HeLa (62764 Activities)

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SLC28A3 Tchem Solute carrier family 28 member 3 (29 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Crotalus adamanteus (3 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 33 mg/mL (196.25 mM)
• Melt Point(°C): 218-222°C
• Molecular Weight: 168.150 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 168.042 Da
• Monoisotopic Mass: 168.042 Da
• Topological Polar Surface Area: 77.800 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 168.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wang Yiying, Pang Yuehong, Yang Yan, Shen Xiaofang.  (2022)  Facile synthesis of recyclable magnetic covalent organic frameworks for adsorption of bisphenol A from aqueous solution.  JOURNAL OF POROUS MATERIALS,  29  (5): (1411-1421).  [PMID:] [10.1007/s10934-022-01266-6]

2. Shu-Ting Cheng, Jin-Yu Qiao, Hong-Ming Zhang, Xiao-Fang Shen, Yue-Hong Pang.  (2024)  Covalent organic framework reinforced hollow fiber bar for extraction and detection of bisphenols from beverages.  FOOD CHEMISTRY,      [PMID:38401314] [10.1016/j.foodchem.2024.138802]

3. Jin-Yu Qiao, Yue-Hong Pang, Zhu-Ying Yan, Xiao-Fang Shen.  (2022)  Electro-enhanced solid-phase microextraction with membrane protection for enrichment of bisphenols in canned meat.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:36323096] [10.1016/j.chroma.2022.463592]