Acetosyringone is a phenolic compound produced from injured plant cells. The virA gene encodes a membrane-bound protein that senses Acetosyringone, phosphorylates itself and activates the vir gene product, which stimulates the transcription of itself and other vir genes. Acetosyringone enhances Agrobacterium-mediated efficient transformation of Dunaliella salina.

Physicochemical Properties

Molecular Formula	C10H12O4
Molecular Weight	196.1999
Exact Mass	196.073
CAS #	2478-38-8
PubChem CID	17198
Appearance	Off-white to light brown solid powder
Density	1.2±0.1 g/cm3
Boiling Point	334.7±37.0 °C at 760 mmHg
Melting Point	124-127 °C(lit.)
Flash Point	131.7±20.0 °C
Vapour Pressure	0.0±0.8 mmHg at 25°C
Index of Refraction	1.528
LogP	1.23
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Heavy Atom Count	14
Complexity	190
Defined Atom Stereocenter Count	0
InChi Key	OJOBTAOGJIWAGB-UHFFFAOYSA-N
InChi Code	InChI=1S/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H3
Chemical Name	1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Acetosyringone, a phenolic substance derived from injured plant cells, stimulates the hydrolysis of additional vir genes by phosphorylating the VirA gene, which codes for membrane-bound cleavage, and activating the virG gene product [1]. The capacity of Agrobacterium Escherichia coli strains to effectively change Dunaliella algae [2].
References	[1]. Acetosyringone treatment duration affects large T-DNA molecule transfer to rice callus. BMC Biotechnol. 2018 Aug 9;18(1):48. [2]. Synergistic Action of D-Glucose and Acetosyringone on Agrobacterium Strains for Efficient Dunaliella Transformation. PLoS One. 2016 Jun 28;11(6):e0158322.
Additional Infomation	Acetosyringone is 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. It has a role as a non-steroidal anti-inflammatory drug, an anti-asthmatic drug, a non-narcotic analgesic, a peripheral nervous system drug and a plant metabolite. It is a member of acetophenones, a dimethoxybenzene and a member of phenols. Acetosyringone has been reported in Atropa belladonna, Triticum aestivum, and other organisms with data available. Acetosyringone is a metabolite found in or produced by Saccharomyces cerevisiae.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~509.68 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.0968 mL	25.4842 mL	50.9684 mL
	5 mM	1.0194 mL	5.0968 mL	10.1937 mL
	10 mM	0.5097 mL	2.5484 mL	5.0968 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.