2',4',6'-Trihydroxyacetophenone

Base Information

• Chemical Name: 2',4',6'-Trihydroxyacetophenone
• CAS No.: 480-66-0
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 29145000
• European Community (EC) Number: 207-556-5
• NSC Number: 54927
• UNII: 8L7XD8830T
• DSSTox Substance ID: DTXSID5060061
• Nikkaji Number: J6.168I
• Wikipedia: 2,4,6-Trihydroxyacetophenone
• Wikidata: Q4596772
• Metabolomics Workbench ID: 43955
• ChEMBL ID: CHEMBL452477
• Mol file: 480-66-0.mol

Synonyms:2,4,-dihydroxy-acetophenone;2,4,6-THA;2,4,6-trihydroxy-acetophenone;2,4,6-trihydroxyacetophenone;4-mono-hydroxy-acetophenone;phloracetophenone;phloroacetophenone

Chemical Property of 2',4',6'-Trihydroxyacetophenone

Chemical Property:

• Appearance/Colour: light brown solid
• Melting Point: 219-221 °C(lit.)
• Refractive Index: 1.5090 (estimate)
• Boiling Point: 333.2 °C at 760 mmHg
• PKA: 7.76±0.23(Predicted)
• Flash Point: 169.5 °C
• PSA: 77.76000
• Density: 1.446 g/cm³
• LogP: 1.00600
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly), Water (Very Slightly,
• Water Solubility.: Soluble in water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

Phloracetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1=C(C=C(C=C1O)O)O
• Uses: Monoacetylphloroglucinol (MAPG) is small molecular weight phenolic metabolite belonging to the phloroglucinol (1,3,5-trihydroxybenzene) family, produced by bacteria including Pseudomonas strains. MAPG exhibits a broad range of biological activity albeit with mostly low potency. In the search for novel actives, MAPG and related metabolites are important metabolites 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. Induced choleresis in rats is mediated through multidrug resistance protein-2 (Mrp2). It enhances bile secretion Induced choleresis in rats is mediated through multidrug resistance protein-2 (Mrp2). It enhances bile secretion.

Technology Process of 2',4',6'-Trihydroxyacetophenone

There total 46 articles about 2',4',6'-Trihydroxyacetophenone 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: 96.2%

3,5-dihydroxyphenol (108-73-6) + acetonitrile (75-05-8,26809-02-9) → 2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5)

Guidance literature:

3,5-dihydroxyphenol; acetonitrile; With hydrogenchloride; zinc(II) chloride; In di-isopropyl ether; at 0 ℃;

With water; for 2h; Reflux;

DOI:10.14233/ajchem.2016.19613

Reference yield: 92.0%

3,5-dihydroxyphenol (108-73-6) + acetic acid butyl ester (123-86-4) → 2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5)

Guidance literature:

With 4-chlorophenylethylamine; copper(I) bromide; at 5 ℃; for 35h; Temperature; Reflux;

Reference yield: 92.0%

1-(2,4,6-tris((tert-butyldimethylsilyl)oxy)phenyl)ethan-1-one (265975-36-8) → 2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5)

Guidance literature:

With N,N,N',N'-tetramethylguanidine; In acetonitrile; at 50 ℃; for 1h;

DOI:10.1021/ol027263d

upstream raw materials:

3,5-dihydroxyphenol

2,4-diacetylphloroglucinol

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

acetyl chloride

Downstream raw materials:

2-hydroxy-4,6-dimethoxyacetophenone

2,6-dihydroxy-4-methoxy-acetophenone

1-[2,4,6-tris-(4-nitro-benzoyloxy)-phenyl]-ethanone

2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone

Refernces

• 1、 Zhou, Wen-Li,Tan, Hai-Bo,Qiu, Sheng-Xiang,Chen, Guang-Ying,Liu, Hong-Xin,Zheng, Chao. "Biomimetic total synthesis and structure confirmation of myrtucommulone K". . p. 1817 - 1821. Retrieved 2017.
• 2、 Wu, Lin,Luo, Jun,Zhang, Yalong,Zhu, Mengdi,Wang, Xiaobing,Luo, Jianguang,Yang, Minghua,Yu, Boyang,Yao, Hequan,Dai, Yue,Guo, Qinglong,Chen, Yijun,Sun, Hongbin,Kong, Lingyi. "Isolation and biomimetic synthesis of (±)-calliviminones A and B, two novel Diels-Alder adducts, from Callistemon viminalis". . p. 229 - 232. Retrieved 2014.
• 3、 Wu, Hongxi,Ren, Jie,Zhao, Lulu,Li, Zhiyu,Ye, Wanli,Yang, Yong,Wang, Jubo,Bian, Jinlei. "Identification of novel androgen receptor degrading agents to treat advanced prostate cancer". . . Retrieved 2021/03/24.
• 4、 Escobar, Gustavo,González, Luis A.,Qui?ones, Wiston,Robledo, Sara,Upegui, Yulieth. "Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones". . . Retrieved 2021/12/02.