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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

AM8440000

F 

10

Hazard Note 

Irritant

HS Code 

29145090

MSDS

• Language:English Provider:3',5'-Dimethoxy-4'-hydroxyacetophenone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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.

References

[1] SHAW C H. Swimming against the tide: Chemotaxis in Agrobacterium[J]. BioEssays, 1991, 13 1: 25-29. DOI: 10.1002/bies.950130105
[2] YONG-WOOG LEE . The sensing of plant signal molecules by Agrobacterium: genetic evidence for direct recognition of phenolic inducers by the VirA protein[J]. Gene, 1996, 179 1: Pages 83-88. DOI: 10.1016/s0378-1119(96)00328-9
[3] RAMACHANDRAN SRINIVASAN  Kodiveri M G. Synergistic Action of D-Glucose and Acetosyringone on Agrobacterium Strains for Efficient Dunaliella Transformation.[J]. PLoS ONE, 2016: e0158322. DOI: 10.1371/journal.pone.0158322

Acetosyringone(2478-38-8)Related Product Information

• 3,4-Dimethoxyacetophenone
• Acetylacetone
• 2-HYDROXYACETOPHENONE
• Dimethyldimethoxysilane
• Acetylspiramycin
• 2'-Methoxyacetophenone
• 4'-Methoxyacetophenone
• 1,1-Dimethoxyethane
• 2'-Hydroxyacetophenone
• Acetaminophen
• 3,5-Dihydroxyacetophenone
• Acetylcholine
• Diphenyldimethoxysilane
• 3',5'-Dimethoxyacetophenone
• Acetylsalicylic acid
• CHLOROPHOSPHONAZO III
• 4'-Hydroxyacetophenone
• Dimethoxymethane