Skip to Content
Merck
All Photos(1)

Documents

61698

Sigma-Aldrich

N-(3-Hydroxyoctanoyl)-DL-homoserine lactone

≥95% (sum of isomers, HPLC)

Synonym(s):

3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)octanamide, 3-Hydroxy-C8-HSL, N-[(RS)-3-Hydroxyoctanoyl]-DL-homoserine lactone

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C12H21NO4
CAS Number:
853799-77-6
Molecular Weight:
243.30
MDL number:
MFCD27952927
UNSPSC Code:
41116134
PubChem Substance ID:
329759646
NACRES:
NA.25

Assay

≥95% (sum of isomers, HPLC)

storage temp.

−20°C

SMILES string

O=C(CC(O)CCCCC)NC1C(OCC1)=O

InChI

1S/C12H21NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h9-10,14H,2-8H2,1H3,(H,13,15)

InChI key

XCZVBYOXRSFQBH-UHFFFAOYSA-N

Biochem/physiol Actions

N-(3-Hydroxyoctanoyl)-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, cell to cell communication among bacteria; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.

Storage Class Code

11 - Combustible Solids

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Bonnie L Bassler
Cell, 109(4), 421-424 (2002-06-28)
In a process called quorum sensing, groups of bacteria communicate with one another to coordinate their behavior and function like a multicellular organism. A diverse array of secreted chemical signal molecules and signal detection apparatuses facilitate highly productive intra- and
M B Miller et al.
Annual review of microbiology, 55, 165-199 (2001-09-07)
Quorum sensing is the regulation of gene expression in response to fluctuations in cell-population density. Quorum sensing bacteria produce and release chemical signal molecules called autoinducers that increase in concentration as a function of cell density. The detection of a
Jie Zhu et al.
Current opinion in pharmacology, 13(5), 688-698 (2013-07-24)
With the emergence of microbial pathogens increasingly resistant against commonly used antibiotics, new treatment strategies are desperately needed. Bacterial quorum sensing has attracted a lot of attention over the last decade as a potential new target for antimicrobial therapy. Interference
David G Davies et al.
Journal of bacteriology, 191(5), 1393-1403 (2008-12-17)
It is well established that in nature, bacteria are found primarily as residents of surface-associated communities called biofilms. These structures form in a sequential process initiated by attachment of cells to a surface, followed by the formation of matrix-enmeshed microcolonies
C Fuqua et al.
Annual review of genetics, 35, 439-468 (2001-11-09)
Quorum sensing is an example of community behavior prevalent among diverse bacterial species. The term "quorum sensing" describes the ability of a microorganism to perceive and respond to microbial population density, usually relying on the production and subsequent response to
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service