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

MedKoo CAT#: 329845

CAS#: 2478-38-8

Description: 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.


Price and Availability

Size
Price

5g
USD 265
Size
Price

10g
USD 465
Size
Price

25g
USD 750

Acetosyringone, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 329845
Name: Acetosyringone
CAS#: 2478-38-8
Chemical Formula: C10H12O4
Exact Mass: 196.0736
Molecular Weight: 196.202
Elemental Analysis: C, 61.22; H, 6.17; O, 32.62


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


Technical Data

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).

Harmonized System Code:
293490


References

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.