2161-86-6 Usage
Chemical Properties
Light Pink Solid
Uses
Different sources of media describe the Uses of 2161-86-6 differently. You can refer to the following data:
1. 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.
2. 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.
Definition
ChEBI: A benzenetriol that is phloroglucinol in which two of the ring hydrogens are replaced by acetyl groups.
Preparation
Preparation by Friedel–Crafts acylation of phloroglucinol, ? with acetic acid, – by using boron trifluoride-acetic acid complex at 28–30° for 18 h (85%)with acetic anhydride, – in the presence of boron trifluoride-ethyl ether complex at 20° for 1 h (80%) – in the presence of zinc chloride at 145–150° for 15 min (25%); – in the presence of concentrated sulfuric acid (24%) ? with acetyl chloride, – (4 equiv.) in the presence of ferric chloride – in ethyl ether in the presence of aluminium chloride at r.t. for 5 days (8).
Biological Activity
2,4-diacetylphloroglucinol is an agent against various plant pathogenic fungi, viruses, bacteria, and nematodes.2,4-diacetylphloroglucinol, a non-nitrogen-containing compound produced by some isolates of p. fluorescens, has been used to increase crop yield by controlling plant root diseases.
in vitro
a previous study was conducted to determine if 2,4-diacetylphloroglucinol was toxic to selected nematodes. the plant-parasitic nematodes including pratylenchus scribneri and xiphinema americanum, heterodera glycines, meloidogyne incognita, and the bacterial-feeding nematodes such as pristionchus pacificus, caenorhabditis elegans, and rhabditis rainai, were found to be immersed in concentrations ranging from 0 to 100 μg/ml of 2,4-diacetylphloroglucinol. moreove, the egg hatch and viability of juveniles and adults were determined, and the results showed that 2,4-diacetylphloroglucinol was toxic to x. americanum adults with an ld50 of 8.3 μg/ml. 2,4-diacetylphloroglucinol could decrease m. incognita egg hatch, but stimulated c. elegans hatch. whereas, the viability of m. incognita j2 and of c. elegans j1 and adults was not affected. there were no observed effects on the other nematodes. these findings indicated that 2,4-diacetylphloroglucinol was not toxic to all nematodes, and did not affect the tested species of beneficial bacterial-feeding nematodes [1].
references
[1] meyer, s. l.f.,halbrendt, j.m.,carta, l.k., et al. toxicity of 2,4-diacetylphloroglucinol (dapg) to plant-parasitic and bacterial-feeding nematodes. journal of nematology 41(4), 274-280 (2009).
Check Digit Verification of cas no
The CAS Registry Mumber 2161-86-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,6 and 1 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2161-86:
(6*2)+(5*1)+(4*6)+(3*1)+(2*8)+(1*6)=66
66 % 10 = 6
So 2161-86-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3
2161-86-6Relevant articles and documents
A large scale synthesis of a natural antibiotic, 2,4- diacetylophloroglucinol (DAPG)
Zakrzewski, Jerzy,Karpinska, Monika,Malinski, Zbigniew
, p. 103 - 106 (2007)
A natural antibiotic, 2,4-diacetylophloroglucinol (DAPG), has been prepared by the acetylation of phloroglucinol (PhL) with acetic anhydride in the presence of boron trifluoride etherate complex. The crude DAPG is efficiently purified using chromatographi
Diacylphloroglucinol derivatives as antioxidant agents: green synthesis, optimisation, in?vitro, and in silico evaluation
Prasetyo, Wahyu E.,Kusumaningsih, Triana,Firdaus, Maulidan,Marliana, Soerya D.,Suryanti, Venty,Artanti, Anif N.,Apriana, Ita,Anggraini, Septin D.
, (2021)
Several derivatives of diacylphloroglucinol (3a–3c and 5a–5b) as an analogue of natural product compound 2,4-diacetylphloroglucinol 3a, were successfully synthesised in an excellent yield via a greener Friedel–Craft acylation using methanesulfonic acid (MSA) as a catalyst under an ultrasound-assisted condition. Operational simplicity, excellent yield, expedient metal-free synthesis, energy-efficient and mild reaction conditions are the outstanding advantages in this procedure. A scaled-up reaction also revealed the practical suitability of this newly developed procedure. The effects of several process variables on 3a were carefully accomplished using response surface methodology (RSM). Moreover, the green credentials of the present protocol have been assessed using several established green metrics and compared to relevant procedures. Along with the monomers, dimeric diacylphloroglucinols (6a–6e) were also synthesised and their in?vitro antioxidant activity of these species were carried out. Furthermore, drug-likeness, density functional theory (DFT), and molecular docking studies were also established.
Highly efficient and green synthesis of diacylphloroglucinol over treated natural zeolite mordenite and the optimization using response surface method (RSM)
Prasetyo, Wahyu Eko,Kusumaningsih, Triana,Firdaus, Maulidan
, p. 3352 - 3372 (2019)
Herein, we report a greener and highly efficient route for the Friedel-Craft acylation of phloroglucinol over Indonesian treated natural zeolite mordenite (nHZMOR) catalyst to provide value-added diacylphloroglucinol derivatives under solvent-free conditi
Toward an efficient and eco-friendly route for the synthesis of dimeric 2,4-diacetyl phloroglucinol and its potential as a SARS-CoV-2 main protease antagonist: Insight from: In silico studies
Kusumaningsih, Triana,Prasetyo, Wahyu E.,Wibowo, Fajar R.,Firdaus, Maulidan
supporting information, p. 7830 - 7843 (2021/05/13)
As a consequence of the unavailability of an anti-viral drug for SARS-CoV-2, the prospect of developing an antiviral drug is of great importance in this current emergency of the COVID-19 pandemic era. To support the enduring research on the improvement of
Total synthesis of dryocrassin ABBA and its analogues with potential inhibitory activity against drug-resistant neuraminidases
Hou, Bo,Liu, Ze,Yang, Xiao-Bei,Zhu, Wen-Fei,Li, Jin-Yu,Yang, Liu,Reng, Fu-Cai,Lv, Yong-Feng,Hu, Jiang-Miao,Liao, Guo-Yang,Zhou, Jun
, p. 3846 - 3852 (2019/07/18)
The stems of Dryopteris crassirhizoma, one of the main components of Lianhua-Qingwen Formula (LQF) was traditionally used for heat-clearing and detoxifying. Dryocrassin ABBA is a key antiviral component in the herbal medicine while the compound is hard to
