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Acetosyringone

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Acetosyringone Basic information

Product Name:
Acetosyringone
Synonyms:
  • SYRINGACETONE
  • 3',5'-DIMETHOXY-4'-HYDROXYACETOPHENONE
  • 3,5-DIMETHOXY-4-HYDROXYACETOPHENONE
  • 4'-HYDROXY-3',5'-DIMETHOXYACETOPHENONE
  • 4-HYDROXY-3,5-DIMETHOXYACETOPHENONE
  • ACETOSYRINGONE
  • 1-(4-hydroxy-3,5-dimethoxyphenyl)-ethanon
  • 1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanone
CAS:
2478-38-8
MF:
C10H12O4
MW:
196.2
EINECS:
219-610-5
Product Categories:
  • plantgrowth
  • Aromatic Acetophenones & Derivatives (substituted)
Mol File:
2478-38-8.mol
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Acetosyringone Chemical Properties

Melting point:
124-127 °C(lit.)
Boiling point:
293.08°C (rough estimate)
Density 
1.2166 (rough estimate)
refractive index 
1.5430 (estimate)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Crystalline Powder
pka
8.19±0.23(Predicted)
color 
Beige to light brown
Odor
at 100.00?%. odorless
Water Solubility 
soluble
BRN 
1966119
LogP
1.699 (est)
CAS DataBase Reference
2478-38-8(CAS DataBase Reference)
NIST Chemistry Reference
Ethanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-(2478-38-8)
EPA Substance Registry System
Acetosyringone (2478-38-8)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
2
RTECS 
AM8440000
10
Hazard Note 
Irritant
HS Code 
29145090

MSDS

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Acetosyringone Usage And Synthesis

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.

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.

Chemical Properties

beige to light brown crystalline powder

Uses

insect attractant, plant hormone

Uses

A buffer also known as acetosyringone that is used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents in vitro.

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.

Preparation

Preparation by adding a solution of 4-hydroxy-3- iodo-5-methoxyacetophenone and cupric chloride in DMF to a solution of sodium methoxide in methanol and heating between 105° and 120° (86%).

Definition

ChEBI: A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.

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