Acetosyringone

Base Information

• Chemical Name: Acetosyringone
• CAS No.: 2478-38-8
• Molecular Formula: C10H12O4
• Molecular Weight: 196.203
• Hs Code.: 29145090
• European Community (EC) Number: 219-610-5
• UNII: 866P45Y84S
• DSSTox Substance ID: DTXSID2062454
• Nikkaji Number: J55.026D
• Wikipedia: Acetosyringone
• Wikidata: Q906309
• Metabolomics Workbench ID: 52908
• ChEMBL ID: CHEMBL224146
• Mol file: 2478-38-8.mol

Synonyms:acetosyringenin;acetosyringone

Chemical Property of Acetosyringone

Chemical Property:

• Appearance/Colour: beige to light brown crystalline powder
• Melting Point: 124-127 °C(lit.)
• Refractive Index: 1.5430 (estimate)
• Boiling Point: 334.7 °C at 760 mmHg
• PKA: 8.19±0.23(Predicted)
• Flash Point: 131.7 °C
• PSA: 55.76000
• Density: 1.172 g/cm³
• LogP: 1.61200
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 190

Purity/Quality:

99%, ^*data from raw suppliers

4’-Hydroxy-3’,5’-dimethoxyacetophenone ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(=O)C1=CC(=C(C(=C1)OC)O)OC
• Uses: 4’-Hydroxy-3’,5’-dimethoxyacetophenone used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents. It is a naturally occuring compound found in plants and used in plant-pathogen recognition. insect attractant, plant hormone A buffer also known as acetosyringone that is used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents in vitro.
• Description: Acetosyringone is a phenol secreted by wounded plant tissues. It induces expression of virulence A genes and chemotaxis in A. tumefaciens strains that contain a tumor-inducing plasmid used to transfer genetic information to plant cells. Acetosyringone is widely used to increase efficacy of genetic transformation for the creation of genetically modified dicotyledonous and monocotyledonous plants.

Technology Process of Acetosyringone

There total 58 articles about Acetosyringone 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%

methyl (3,4,5-trimethoxyphenyl) ketone (1136-86-3) → 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone (2478-38-8)

Guidance literature:

With lithium thioethoxide; In N,N-dimethyl-formamide; at 70 ℃; for 0.25h; regioselective reaction; Inert atmosphere; Microwave irradiation;

DOI:10.1055/s-2008-1077949

Reference yield: 82.0%

1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol (33900-62-8) → 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone (2478-38-8) + 2,6-dimethoxy-p-quinone (530-55-2,26547-64-8)

Guidance literature:

With oxygen; (pyridine)cobalt; In methanol; for 24h; under 2585.7 Torr; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00113a020

Reference yield: 80.0%

acetic acid 2,6-dimethoxy-phenyl ester (944-99-0) → 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone (2478-38-8)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In toluene; for 1h; Heating;

DOI:10.1081/SCC-120030693

upstream raw materials:

acetic acid 2,6-dimethoxy-phenyl ester

1-(4-hydroxy-3-iodo-5-methoxy-phenyl)ethan-1-one

sodium methylate

1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone benzyl ether

Downstream raw materials:

3,5-dimethoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)acetophenone

1-(4-acetoxy-3,5-dimethoxy-phenyl)-ethanone

1,2,3,4-tetra-O-acetyl-L-fucopyranose

3,5-Dimethoxy-4-(2,3,4-tri-O-acetyl-β-L-fucopyranosyloxy)acetophenone

Refernces

• 1、 Negrel, Jonathan,Javelle, Francine. "The biosynthesis of acetovanillone in tobacco cell-suspension cultures". . p. 751 - 759. Retrieved 2010.
• 2、 -. "Synthesis method of 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one". Paragraph 0019; 0025-0027; 0028; 0032-0033; 0034; 0038-0039. . Retrieved 2020/05/30.
• 3、 Hu, Zhenhua,Li, Suxiang,Lu, Fachuang,Shi, Lanlan,Wang, Chen,Yue, Fengxia,Zhang, Han,Zhao, Chengke. "Profiling of the formation of lignin-derived monomers and dimers from: Eucalyptus alkali lignin". supporting information. p. 7366 - 7375. Retrieved 2020/11/18.