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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O4
Molecular Weight 196.1999
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETOSYRINGONE

SMILES

COC1=CC(=CC(OC)=C1O)C(C)=O

InChI

InChIKey=OJOBTAOGJIWAGB-UHFFFAOYSA-N
InChI=1S/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H3

HIDE SMILES / InChI
Acetosyringone is a naturally occurring compound found in a wide variety of plants. It is best known for its involvement in plant-pathogen recognition and its biotechnical applications for enhancing plant transformation efficiency. There has been limited investigation of human or animal applications. In one instance Acetosyringone demonstrated accelerated hair regrowth in a mouse model.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Agrobacterium tumefaciens-mediated genetic transformation of a recalcitrant grain legume, lentil (Lens culinaris Medik).
2009-03
Development of an activation tagging system for the basidiomycetous medicinal fungus Antrodia cinnamomea.
2009-03
FORCA, a promoter element that responds to crosstalk between defense and light signaling.
2009-01-07
Genetic transformation and regeneration of Sesbania drummondii using cotyledonary nodes.
2009-01
Conidiation color mutants of Aspergillus fumigatus are highly pathogenic to the heterologous insect host Galleria mellonella.
2009
Role of acetosyringone in the accumulation of a set of RNAs in the arbuscular mycorrhiza fungus Glomus intraradices.
2008-12
Engineering and Applications of fungal laccases for organic synthesis.
2008-11-20
Transgenic rice expressing Allium sativum leaf agglutinin (ASAL) exhibits high-level resistance against major sap-sucking pests.
2008-10-14
Decolourization of recalcitrant dyes with a laccase from Streptomyces coelicolor under alkaline conditions.
2008-10
Transgenic tomatoes expressing human beta-amyloid for use as a vaccine against Alzheimer's disease.
2008-10
High-throughput Agrobacterium-mediated barley transformation.
2008-09-26
The Arabidopsis thaliana response regulator ARR22 is a putative AHP phospho-histidine phosphatase expressed in the chalaza of developing seeds.
2008-07-15
[Optimization of tomato genetic transformation, kanamycin-resistant screening and seed selection].
2008-07
Expression of HIV-1 antigens in plants as potential subunit vaccines.
2008-06-23
The histidine kinase AHK5 integrates endogenous and environmental signals in Arabidopsis guard cells.
2008-06-18
[Transformation of Astragalus melilotoides Pall with AtNHX1 gene and the expression of salinity tolerance of transformants].
2008-06
Off-line pyrolysis and compound-specific stable carbon isotope analysis of lignin moieties: a new method for determining the fate of lignin residues in soil.
2008-06
Role of CheY1 and CheY2 in the chemotaxis of A. tumefaciens toward acetosyringone.
2008-06
Hypericum perforatum plant cells reduce Agrobacterium viability during co-cultivation.
2008-05
The SNF1-type serine-threonine protein kinase SAPK4 regulates stress-responsive gene expression in rice.
2008-04-28
Histoplasma requires SID1, a member of an iron-regulated siderophore gene cluster, for host colonization.
2008-04-11
Tobacco mosaic virus movement protein enhances the spread of RNA silencing.
2008-04-04
Scale-up of Agrobacterium-mediated transient protein expression in bioreactor-grown Nicotiana glutinosa plant cell suspension culture.
2008-03-14
Salt tolerance conferred by overexpression of Arabidopsis vacuolar Na(+)/H (+) antiporter gene AtNHX1 in common buckwheat (Fagopyrum esculentum).
2008-02
Optimized cDNA libraries for virus-induced gene silencing (VIGS) using tobacco rattle virus.
2008-01-22
A modified Gateway cloning strategy for overexpressing tagged proteins in plants.
2008-01-22
Different subcellular localizations and functions of Arabidopsis myosin VIII.
2008-01-08
Specific targeting of a plasmodesmal protein affecting cell-to-cell communication.
2008-01
A constructed alkaline consortium and its dynamics in treating alkaline black liquor with very high pollution load.
2008
The Arabidopsis cytochrome P450 CYP86A1 encodes a fatty acid omega-hydroxylase involved in suberin monomer biosynthesis.
2008
Ethylene production in plants during transformation suppresses vir gene expression in Agrobacterium tumefaciens.
2008
Methoxyphenols and levoglucosan ratios in PM2.5 from wheat and Kentucky bluegrass stubble burning in eastern Washington and northern Idaho.
2007-11-15
Interference by Mes [2-(4-morpholino)ethanesulfonic acid] and related buffers with phenolic oxidation by peroxidase.
2007-11-01
Agrobacterium tumefaciens-mediated transformation of Narcissus tazzeta var. chinensis.
2007-09
High-efficiency protein expression in plants from agroinfection-compatible Tobacco mosaic virus expression vectors.
2007-08-27
Optimization of phenolic compounds analysis by capillary electrophoresis.
2007-06-15
Removal of lipophilic extractives from paper pulp by laccase and lignin-derived phenols as natural mediators.
2007-06-01
Agrobacterium-mediated transformation of protocorm-like bodies in Cymbidium.
2007-06
Translational control of recombinant human acetylcholinesterase accumulation in plants.
2007-05-30
Transformation of polycyclic aromatic hydrocarbons by laccase is strongly enhanced by phenolic compounds present in soil.
2007-04-15
A novel role for the TIR domain in association with pathogen-derived elicitors.
2007-03
Development of genotype-independent regeneration system for transformation of rice (Oryza sativa ssp. indica).
2007-03
Association of six YFP-myosin XI-tail fusions with mobile plant cell organelles.
2007-02-09
A study of expression of hypoxanthine and cytokinin-like compounds in the presence of acetosyringone and dexamethasone in phototrophic purple bacteria and their sensor histidine kinases: biochemical and computer analysis.
2007-02-09
Red colouration in apple fruit is due to the activity of the MYB transcription factor, MdMYB10.
2007-02
Methods for transient assay of gene function in floral tissues.
2007-01-08
Genetic transformation of barley (Hordeum vulgare L.) via infection of androgenetic pollen cultures with Agrobacterium tumefaciens.
2006-03
Mushroom (Agaricus bisporus).
2006
Banana (Musa sp.).
2006
Agrobacterium-Mediated Transformation of Fusarium oxysporum: An Efficient Tool for Insertional Mutagenesis and Gene Transfer.
2001-02
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: the referenced study was conducted on mouse
The hair on the back of 9-week old male C3H/He mice was clipped off and the clipped area was treated with softening cream for 5 or 10 min and washed. After 24 hours a test sample of Acetosyringone (0.001, 0.01, 0.1, 0.5, 1.0 mg) was applied topically once per day for 1 or 3 days. Hair regrowth was monitored relative to controls. Acetosyringone promoted significantly greater hair regrowth at all concentrations compared to controls and did not cause skin irritation.
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
ACETOSYRINGENIN
Preferred Name English
ACETOSYRINGONE
Common Name English
4'-HYDROXY-3',5'-DIMETHOXYACETOPHENONE
Systematic Name English
Code System Code Type Description
CHEBI
2404
Created by admin on Mon Mar 31 19:51:33 GMT 2025 , Edited by admin on Mon Mar 31 19:51:33 GMT 2025
PRIMARY
WIKIPEDIA
ACETOSYRINGONE
Created by admin on Mon Mar 31 19:51:33 GMT 2025 , Edited by admin on Mon Mar 31 19:51:33 GMT 2025
PRIMARY
CAS
2478-38-8
Created by admin on Mon Mar 31 19:51:33 GMT 2025 , Edited by admin on Mon Mar 31 19:51:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
219-610-5
Created by admin on Mon Mar 31 19:51:33 GMT 2025 , Edited by admin on Mon Mar 31 19:51:33 GMT 2025
PRIMARY
PUBCHEM
17198
Created by admin on Mon Mar 31 19:51:33 GMT 2025 , Edited by admin on Mon Mar 31 19:51:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID2062454
Created by admin on Mon Mar 31 19:51:33 GMT 2025 , Edited by admin on Mon Mar 31 19:51:33 GMT 2025
PRIMARY
FDA UNII
866P45Y84S
Created by admin on Mon Mar 31 19:51:33 GMT 2025 , Edited by admin on Mon Mar 31 19:51:33 GMT 2025
PRIMARY