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MedKoo Cat#: 329845 | Name: Acetosyringone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Acetosyringone is a phenolic natural product, and is a chemical compound related to acetophenone and 2,6-dimethoxyphenol. It was first described in relation to lignan/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes.

Chemical Structure

Acetosyringone
Acetosyringone
CAS#2478-38-8

Theoretical Analysis

MedKoo Cat#: 329845

Name: Acetosyringone

CAS#: 2478-38-8

Chemical Formula: C10H12O4

Exact Mass: 196.0736

Molecular Weight: 196.20

Elemental Analysis: C, 61.22; H, 6.17; O, 32.62

Price and Availability

Size Price Availability Quantity
5g USD 285.00 2 Weeks
10g USD 450.00 2 Weeks
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Synonym
Acetosyringone
IUPAC/Chemical Name
4'-Hydroxy-3',5'-dimethoxyacetophenone
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
SMILES Code
CC(C1=CC(OC)=C(O)C(OC)=C1)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 196.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Negrel J, Javelle F, Wipf D. Detection of an O-methyltransferase synthesising acetosyringone in methyl jasmonate-treated tobacco cell-suspensions cultures. Phytochemistry. 2014 Mar;99:52-60. doi: 10.1016/j.phytochem.2013.12.013. Epub 2014 Jan 17. PubMed PMID: 24445177. 2: Manfroi E, Yamazaki-Lau E, Grando MF, Roesler EA. Acetosyringone, pH and temperature effects on transient genetic transformation of immature embryos of Brazilian wheat genotypes by Agrobacterium tumefaciens. Genet Mol Biol. 2015 Dec;38(4):470-6. doi: 10.1590/S1415-475738420150026. Epub 2015 Nov 3. PubMed PMID: 26537604; PubMed Central PMCID: PMC4763325. 3: Srinivasan R, Gothandam KM. Synergistic Action of D-Glucose and Acetosyringone on Agrobacterium Strains for Efficient Dunaliella Transformation. PLoS One. 2016 Jun 28;11(6):e0158322. doi: 10.1371/journal.pone.0158322. eCollection 2016. PubMed PMID: 27351975; PubMed Central PMCID: PMC4924854. 4: Kim Y, Miyashita M, Miyagawa H. Early signaling events induced by the peptide elicitor PIP-1 necessary for acetosyringone accumulation in tobacco cells. Biosci Biotechnol Biochem. 2016 Jun;80(6):1054-7. doi: 10.1080/09168451.2016.1151342. Epub 2016 Feb 29. PubMed PMID: 26924306. 5: Hao S, Chen K, Cao L, Zhu X, Luo G, Zhang S, Chen J. Separation of high-purity syringol and acetosyringone from rice straw-derived bio-oil by combining the basification-acidification process and column chromatography. Electrophoresis. 2016 Oct;37(19):2522-2530. doi: 10.1002/elps.201600126. Epub 2016 Aug 2. PubMed PMID: 27482944. 6: Baker CJ, Mock NM, Whitaker BD, Roberts DP, Rice CP, Deahl KL, Aver'yanov AA. Involvement of acetosyringone in plant-pathogen recognition. Biochem Biophys Res Commun. 2005 Mar 4;328(1):130-6. PubMed PMID: 15670760. 7: Shaw CH, Ashby AM, Brown A, Royal C, Loake GJ, Shaw CH. virA and virG are the Ti-plasmid functions required for chemotaxis of Agrobacterium tumefaciens towards acetosyringone. Mol Microbiol. 1988 May;2(3):413-7. PubMed PMID: 3398775. 8: Hua SS. Inhibitory effect of acetosyringone on two aflatoxin biosynthetic genes. Lett Appl Microbiol. 2001 Apr;32(4):278-81. PubMed PMID: 11298941. 9: Fortin C, Nester EW, Dion P. Growth inhibition and loss of virulence in cultures of Agrobacterium tumefaciens treated with acetosyringone. J Bacteriol. 1992 Sep;174(17):5676-85. PubMed PMID: 1512200; PubMed Central PMCID: PMC206515. 10: Ankenbauer RG, Best EA, Palanca CA, Nester EW. Mutants of the Agrobacterium tumefaciens virA gene exhibiting acetosyringone-independent expression of the vir regulon. Mol Plant Microbe Interact. 1991 Jul-Aug;4(4):400-6. PubMed PMID: 1799700. 11: Harighi B. Genetic evidence for CheB- and CheR-dependent chemotaxis system in A. tumefaciens toward acetosyringone. Microbiol Res. 2009;164(6):634-41. doi: 10.1016/j.micres.2008.11.001. Epub 2009 Feb 23. PubMed PMID: 19231145. 12: Flores-Gómez E, Gómez-Silva L, Ruiz-Medrano R, Xoconostle-Cázeres B. Role of acetosyringone in the accumulation of a set of RNAs in the arbuscular mycorrhiza fungus Glomus intraradices. Int Microbiol. 2008 Dec;11(4):275-82. PubMed PMID: 19204900. 13: Saha P, Blumwald E. Spike-dip transformation of Setaria viridis. Plant J. 2016 Apr;86(1):89-101. doi: 10.1111/tpj.13148. Epub 2016 Mar 30. PubMed PMID: 26932666. 14: Turk SC, van Lange RP, Regensburg-Tuïnk TJ, Hooykaas PJ. Localization of the VirA domain involved in acetosyringone-mediated vir gene induction in Agrobacterium tumefaciens. Plant Mol Biol. 1994 Aug;25(5):899-907. PubMed PMID: 8075405. 15: Lipp João KH, Brown TA. Enhanced transformation of tomato co-cultivated with Agrobacterium tumefaciens C58C1Rif(r)::pGSFR1161 in the presence of acetosyringone. Plant Cell Rep. 1993 May;12(7-8):422-5. doi: 10.1007/BF00234705. PubMed PMID: 24197345. 16: Blount JW, Masoud S, Sumner LW, Huhman D, Dixon RA. Over-expression of cinnamate 4-hydroxylase leads to increased accumulation of acetosyringone in elicited tobacco cell-suspension cultures. Planta. 2002 Apr;214(6):902-10. Epub 2001 Dec 11. PubMed PMID: 11941467. 17: Banta LM, Joerger RD, Howitz VR, Campbell AM, Binns AN. Glu-255 outside the predicted ChvE binding site in VirA is crucial for sugar enhancement of acetosyringone perception by Agrobacterium tumefaciens. J Bacteriol. 1994 Jun;176(11):3242-9. PubMed PMID: 8195079; PubMed Central PMCID: PMC205494. 18: Lai EM, Shih HW, Wen SR, Cheng MW, Hwang HH, Chiu SH. Proteomic analysis of Agrobacterium tumefaciens response to the Vir gene inducer acetosyringone. Proteomics. 2006 Jul;6(14):4130-6. PubMed PMID: 16791832. 19: Harighi B. Role of CheY1 and CheY2 in the chemotaxis of A. tumefaciens toward acetosyringone. Curr Microbiol. 2008 Jun;56(6):547-52. doi: 10.1007/s00284-008-9120-1. Epub 2008 Mar 11. PubMed PMID: 18330636. 20: Sheikholeslam SN, Weeks DP. Acetosyringone promotes high efficiency transformation of Arabidopsis thaliana explants by Agrobacterium tumefaciens. Plant Mol Biol. 1987 Jul;8(4):291-8. doi: 10.1007/BF00021308. PubMed PMID: 24301191.