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H7890

Sigma-Aldrich

L-Homoserine lactone hydrochloride

suitable for ligand binding assays

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About This Item

Empirical Formula (Hill Notation):
C4H7NO2 · HCl
CAS Number:
2185-02-6
Molecular Weight:
137.56
MDL number:
MFCD00058172
UNSPSC Code:
12352209
PubChem Substance ID:
24895811
NACRES:
NA.26

product name

L-Homoserine lactone hydrochloride,

form

powder

Quality Level

200

technique(s)

ligand binding assay: suitable

color

white

storage temp.

−20°C

SMILES string

Cl.N[C@H]1CCOC1=O

InChI

1S/C4H7NO2.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1

InChI key

XBKCXPRYTLOQKS-DFWYDOINSA-N

General description

L-Homoserine lactone (HSL), also called acyl-HSL, comprises a homoserine lactone ring and a fatty acyl side. The levels of acyl-HSL in bacteria is dictated by the availability of the substrates and acyl-homoserine lactones synthase.

Application

L-Homoserine lactone hydrochloride has been used as an inhibitor for arterial smooth muscle contraction.

Biochem/physiol Actions

L-Homoserine lactone inhibition reduces virulence factors and halts inflammation and tissue damage. In Pseudomonas aeruginosa it controls virulence factor production and biofilm formation. In Agrobacterium tumefaciens, it is essential for conjugal transfer.
Acylated L-Homoserine lactone(s) are used to study bacterial quorum-sensing signaling mechanisms.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

H7890-VAR:
H7890-5G:
H7890-1G:
H7890-BULK:
H7890-250MG:

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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Defining the structure and function of acyl-homoserine lactone autoinducers
Churchill MEA, et al.
Methods in Molecular Biology, 692(23), 159-171 (2011)
Long-chain acyl-homoserine lactone quorum-sensing regulation of Rhodobacter capsulatus gene transfer agent production
Schaefer AL, et al.
Journal of Bacteriology, 184(23), 6515-6521 (2002)
The Pseudomonas aeruginosa quorum-sensing signal molecule, N-(3-oxododecanoyl)-l-homoserine lactone, inhibits porcine arterial smooth muscle contraction
Lawrence RN, et al.
British Journal of Pharmacology, 128(4), 845-848 (1999)
Adam Schikora et al.
Plant physiology, 157(3), 1407-1418 (2011-09-24)
Pathogenic and symbiotic bacteria rely on quorum sensing to coordinate the collective behavior during the interactions with their eukaryotic hosts. Many Gram-negative bacteria use N-acyl-homoserine lactones (AHLs) as signals in such communication. Here we show that plants have evolved means
Inhibiting N-acyl-homoserine lactone synthesis and quenching Pseudomonas quinolone quorum sensing to attenuate virulence
Chan KG, et al.
Frontiers in Microbiology, 6, 1173-1173 (2015)
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