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07077

Sigma-Aldrich

N-(p-Coumaroyl)-L-homoserine lactone

≥94% (HPLC)

Synonym(s):

p-Coumaroyl (S)-(−)α-amino-γ-butyrolactone, pC-HSL

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About This Item

Empirical Formula (Hill Notation):
C13H13NO4
Molecular Weight:
247.25
MDL number:
MFCD12912377
UNSPSC Code:
12352209
PubChem Substance ID:
329748342
NACRES:
NA.25

assay

≥94% (HPLC)

form

powder

optical activity

[α]/D -23.0±3.0°, c = 1% in ethanol

color

white to off-white

mp

201.2 °C

application(s)

cell analysis

storage temp.

2-8°C

SMILES string

Oc1ccc(\C=C\C(=O)N[C@H]2CCOC2=O)cc1

InChI

1S/C13H13NO4/c15-10-4-1-9(2-5-10)3-6-12(16)14-11-7-8-18-13(11)17/h1-6,11,15H,7-8H2,(H,14,16)/b6-3+/t11-/m0/s1

InChI key

CCIXZFJYFQJTGK-GQOHGMTASA-N

Application

N-(p-Coumaroyl)-L-homoserine lactone, or pC-HSL, can be used to study microbiology, quorum sensing and signaling compounds. pC-HSL has been used to study the activity of the Rhodopseudomonas palustris p-coumaroyl-homoserine lactone-responsive transcription factor RpaR.

Biochem/physiol Actions

New type of bacterial, quorum sensing signal compound. Quorum sensing mechanism has been investigated in Rhodopseudomonas palustris, but the signal compound has been discovered in other bacteria such as Bradyrhizobium sp. or Silicibacter pomeroyi.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Amy L Schaefer et al.
Nature, 454(7204), 595-599 (2008-06-20)
Quorum sensing is a term used to describe cell-to-cell communication that allows cell-density-dependent gene expression. Many bacteria use acyl-homoserine lactone (acyl-HSL) synthases to generate fatty acyl-HSL quorum-sensing signals, which function with signal receptors to control expression of specific genes. The
Hidetada Hirakawa et al.
Journal of bacteriology, 193(10), 2598-2607 (2011-03-08)
The Rhodopseudomonas palustris transcriptional regulator RpaR responds to the RpaI-synthesized quorum-sensing signal p-coumaroyl-homoserine lactone (pC-HSL). Other characterized RpaR homologs respond to fatty acyl-HSLs. We show here that RpaR functions as a transcriptional activator, which binds directly to the rpaI promoter.
Nicolas Kylilis et al.
Nature communications, 9(1), 2677-2677 (2018-07-12)
Advancing synthetic biology to the multicellular level requires the development of multiple cell-to-cell communication channels that propagate information with minimal signal interference. The development of quorum-sensing devices, the cornerstone technology for building microbial communities with coordinated system behaviour, has largely
Sun-Young Kang et al.
Microbial cell factories, 14, 191-191 (2015-11-27)
Quorum sensing (QS) networks are more commonly known as acyl homoserine lactone (HSL) networks. Recently, p-coumaroyl-HSL has been found in a photosynthetic bacterium. p-coumaroyl-HSL is derived from a lignin monomer, p-coumaric acid, rather than a fatty acyl group. The p-coumaroyl-HSL

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