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68224

N-Dodecanoyl-L-homoserine lactone

Name: <I>N</I>-Dodecanoyl-<SC>L</SC>-homoserine lactone
Brand: SIGMA

≥96% (HPLC), suitable for mass spectrometry (MS)

Synonym(s):

N-Lauroyl-L-homoserine lactone, N-[(3S)-Tetrahydro-2-oxo-3-furanyl]dodecanamide, C12-HSL

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₂₉NO₃

CAS Number:

137173-46-7

Molecular Weight:

283.41

NACRES:

NA.28

PubChem Substance ID:

329760775

UNSPSC Code:

12352211

MDL number:

MFCD11976890

Beilstein/REAXYS Number:

9281984

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Properties

Product Name

N-Dodecanoyl-L-homoserine lactone, ≥96% (HPLC)

Quality Segment

100

assay

≥96% (HPLC)

form

powder or crystals

optical activity

[α]/D -25±5°, c = 0.2 in methanol

technique(s)

mass spectrometry (MS): suitable

color

white to off-white

suitability

conforms to structure for Proton NMR spectrum

storage temp.

−20°C

SMILES string

O=C1OCC[C@@H]1NC(CCCCCCCCCCC)=O

InChI

1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1

InChI key

WILLZMOKUUPJSL-AWEZNQCLSA-N

Description

Biochem/physiol Actions

N-Dodecanoyl-L-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 .

Quorum-sensing signal generation

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hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c