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49619

Sigma-Aldrich

cis-2-Dodecenoic acid

≥95.0% (HPLC)

Synonym(s):

BDSF, Burkholderia cenocepacia diffusible signal factor

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About This Item

Empirical Formula (Hill Notation):
C12H22O2
CAS Number:
55928-65-9
Molecular Weight:
198.30
Beilstein:
1722818
MDL number:
MFCD16661220
UNSPSC Code:
12352106
PubChem Substance ID:
329757488
NACRES:
NA.25

Quality Level

100

Assay

≥95.0% (HPLC)

storage temp.

−20°C

SMILES string

CCCCCCCCC\C=C/C(O)=O

InChI

1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h10-11H,2-9H2,1H3,(H,13,14)/b11-10-

InChI key

PAWGRNGPMLVJQH-KHPPLWFESA-N

Biochem/physiol Actions

Burkholderia cenocepacia produces a diffusible fatty acid signal molecule, cis-2-dodecenoic acid (BDSF), that has been implicated in interspecies and interkingdom communication.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

CorrosionEnvironment
GHS05,GHS09

Signal Word

Danger

Hazard Statements

H318,H411

Precautionary Statements

P273 - P280 - P305 + P351 + P338

Hazard Classifications

Aquatic Chronic 2 - Eye Dam. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yinyue Deng et al.
BMC microbiology, 13, 148-148 (2013-07-03)
Burkholderia cenocepacia employs both N-Acyl homoserine lactone (AHL) and cis-2-dodecenoic acid (BDSF) quorum sensing (QS) systems in regulation of bacterial virulence. It was shown recently that disruption of BDSF synthase RpfFBc caused a reduction of AHL signal production in B.
Robert P Ryan et al.
Journal of bacteriology, 191(15), 5013-5019 (2009-06-02)
Burkholderia cenocepacia produces a diffusible fatty acid signal molecule, cis-2-dodecenoic acid (BDSF), that has been implicated in interspecies and interkingdom communication. Here, we show that BDSF also acts as an intraspecies signal in B. cenocepacia to control factors contributing to
Rimi Chowdhury et al.
PLoS pathogens, 17(2), e1009357-e1009357 (2021-02-23)
Successful intestinal infection by Salmonella requires optimized invasion of the gut epithelium, a function that is energetically costly. Salmonella have therefore evolved to intricately regulate the expression of their virulence determinants by utilizing specific environmental cues. Here we show that
Nadine Schmid et al.
PloS one, 7(11), e49966-e49966 (2012-11-28)
Quorum sensing in Burkholderia cenocepacia H111 involves two signalling systems that depend on different signal molecules, namely N-acyl homoserine lactones (AHLs) and the diffusible signal factor cis-2-dodecenoic acid (BDSF). Previous studies have shown that AHLs and BDSF control similar phenotypic
Orlin Filipov et al.
Archives of orthopaedic and trauma surgery, 137(6), 779-788 (2017-04-10)
Osteosynthesis of femoral neck fractures is related up to 46% rate of complications. The novel method of biplane double-supported screw fixation (BDSF; Filipov's method) offers better stability using three medially diverging cannulated screws with two of them buttressed on the
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