2,4-Diacetylphloroglucinol

Base Information

• Chemical Name: 2,4-Diacetylphloroglucinol
• CAS No.: 2161-86-6
• Molecular Formula: C10H10 O5
• Molecular Weight: 210.186
• Hs Code.: 2914400090
• European Community (EC) Number: 640-549-9
• UNII: 8XV4YYO3WN
• DSSTox Substance ID: DTXSID10175995
• Nikkaji Number: J80.411H
• Wikipedia: 2,4-Diacetylphloroglucinol
• Wikidata: Q4596777
• Metabolomics Workbench ID: 98836
• ChEMBL ID: CHEMBL276139
• Mol file: 2161-86-6.mol

Synonyms:2,4-DAPG;2,4-diAc-phloroglucinol;2,4-diacetylphloroglucinol

Chemical Property of 2,4-Diacetylphloroglucinol

Chemical Property:

• Vapor Pressure: 3.81E-06mmHg at 25°C
• Melting Point: 164 °C
• Boiling Point: 374.7°Cat760mmHg
• PKA: 7.67±0.28(Predicted)
• Flash Point: 194.6°C
• PSA: 94.83000
• Density: 1.422g/cm³
• LogP: 1.20860
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 210.05282342
• Heavy Atom Count: 15
• Complexity: 249

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

2,4-Diacetylphloroglucinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C(=C(C=C1O)O)C(=O)C)O
• Uses: A secondary metabolite of P. Fluorescens strain CHAO which is a pathogen suppressor as well as showing inhibitory effects on bacteria, fungi, and plants. Also show marked antiviral activity against both RNA virus with envelop (vesicular stomatitis virus) and a DNA Virus with envelop (herpes simplex virus type I). Furthermore, it showed antagonistic activity against both thromboxane A2 and leukotriene D4. Diacetylphloroglucinol (DAPG) is a small molecular weight, phenolic metabolite belonging to the phloroglucinol (1,3,5- trihydroxybenzene) family produced by bacteria, including Pseudomonas strains. DAPG exhibits a broad range of biological activities, albeit with mostly low potency. In the search for novel actives, DAPG and related metabolites are important for dereplication to eliminate leads due to high amounts of weakly potent actives. Although weakly active, this family appears to be important in the biocontrol of plant diseases by some Pseudomonas strains.

Technology Process of 2,4-Diacetylphloroglucinol

There total 22 articles about 2,4-Diacetylphloroglucinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

3,5-dihydroxyphenol (108-73-6) + acetic anhydride (108-24-7) → 2,4-diacetylphloroglucinol (2161-86-6)

Guidance literature:

With silica sulphuric acid; In neat (no solvent); at 60 ℃; for 0.333333h; Temperature; Reagent/catalyst; Catalytic behavior; Green chemistry;

DOI:10.1039/d0ra05424k

Reference yield: 94.0%

3,5-dihydroxyphenol (108-73-6) + acetyl chloride (75-36-5) → 2,4-diacetylphloroglucinol (2161-86-6)

Guidance literature:

With methanesulfonic acid; acetic acid; at 80 ℃; for 0.5h; Neat (no solvent);

DOI:10.1016/j.bmcl.2012.01.089

Reference yield: 92.0%

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) + acetic anhydride (108-24-7) → 2,4-diacetylphloroglucinol (2161-86-6)

Guidance literature:

With boron trifluoride diethyl etherate; acetic acid; for 21h; Heating;

DOI:10.1016/j.bmc.2004.12.040

upstream raw materials:

1,3,5-triacetoxybenzene

1,3,5-triacetyl-2,4,6-trihydroxybenzene

3,5-dihydroxyphenol

acetic anhydride

Downstream raw materials:

3'-acetyl-2',4'-dihydroxy-6'-methoxyacetophenone

2,4,6-tribromophloroglucinol

1,3,5-triacetoxy-2,4-diacetyl-benzene

5-acetoxy-2,4-diacetyl-1,3-dihydroxybenzene

Refernces

• 1、 Bharate, Jaideep B.,Batarseh, Yazan S.,Wani, Abubakar,Sharma, Sadhana,Vishwakarma, Ram A.,Kaddoumi, Amal,Kumar, Ajay,Bharate, Sandip B.. "Synthesis and P-glycoprotein induction activity of colupulone analogs". . p. 5488 - 5496. Retrieved 2015.
• 2、 Marchand, Patrice A.,Weller, David M.,Bonsall, Robert F.. "Convenient synthesis of 2,4-diacetylphloroglucinol a natural antibiotic involved in the control of take-all disease of wheat". . p. 1882 - 1887. Retrieved 2000.
• 3、 Firdaus, Maulidan,Kusumaningsih, Triana,Prasetyo, Wahyu Eko. "A greatly improved procedure for the synthesis of an antibiotic-drug candidate 2,4-diacetylphloroglucinol over silica sulphuric acid catalyst: multivariate optimisation and environmental assessment protocol comparison by metrics". . p. 31824 - 31837. Retrieved 2020.
• 4、 Perera, Shashika,Fernando, Asantha,Dallman, Johnathan,Weeramange, Chamitha,Lansakara, Ashabha,Nguyen, Thi,Rafferty, Ryan J.. "Construction and Biological Evaluation of Small Libraries Based on the Intermediates within the Total Synthesis of Uvaretin". . p. 1631 - 1639. Retrieved 2021/04/29.