N-(3-Oxooctanoyl)-L-homoserine lactone

Chemodex
Product Code: CDX-O0058
Product Group: Other Biochemicals
Supplier: Chemodex
CodeSizePrice
CDX-O0058-M01010 mg£72.00
Quantity:
CDX-O0058-M100100 mg£316.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
-20°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
3-oxo-C8-HSL; 3OC8-HSL; N-(beta-Ketooctanoyl)-L-homoserine
Appearance:
White solid.
CAS:
147795-39-9
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light and moisture.
InChi:
InChI=1S/C12H19NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h10H,2-8H2,1H3,(H,13,15)/t10-/m0/s1
InChiKey:
FXCMGCFNLNFLSH-JTQLQIEISA-N
Long Description:
Chemical. CAS: 147795-39-9. Formula: C12H19NO4. MW: 241.3. Synthetic. N-(3-Oxooctanoyl)-L-homoserine lactone is a small diffusible signaling molecule and is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) are involved in quorum sensing, controlling gene expression, and cellular metabolism. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. This compound stimulates the tra gene expression. It is an autoinducer and potent antagonist. Promotes the expression of the transcriptional activator (and LuxR homolog) TraR, in the gram-negative bacterium A. tumefaciens.
MDL:
MFCD08277025
Molecular Formula:
C12H19NO4
Molecular Weight:
241.3
Package Type:
Vial
Product Description:
N-(3-Oxooctanoyl)-L-homoserine lactone is a small diffusible signaling molecule and is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) are involved in quorum sensing, controlling gene expression, and cellular metabolism. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. This compound stimulates the tra gene expression. It is an autoinducer and potent antagonist. Promotes the expression of the transcriptional activator (and LuxR homolog) TraR, in the gram-negative bacterium A. tumefaciens.
Purity:
>97% (HPLC)
SMILES:
[H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCCCC
Solubility Chemicals:
Soluble in chloroform.
Source / Host:
Synthetic.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

References

(1) A. Eberhard, et al.; Arch. Microbiol. 146, 35 (1986) | (2) J. Zhu, et al.; J. Bacteriol. 180, 5398 (1998) | (3) M. Teplitski, et al.; Arch. Microbiol. 180, 494 (2003) | (4) T.A. Gould, et al.; J. Bacteriol. 188, 773 (2006) | (5) C.G.N. Penalver, et al.; FEBS Lett. 580, 561 (2006) | (6) J.C.A. Janssens, et al.; Appl. Environ. Microbiol. 73, 535 (2007) | (7) A.M. Pomini & A.J. Marsaioli; J. Nat. Prod. 71, 1032 (2008) | (8) R.L. Frey, et al.; Environ. Sci. Tech. 44, 7465 (2010) | (9) A.E. McClean, et al.; Phytopathol. 102, 195 (2012) | (10) C. Miao, et al.; BBRC 427, 293 (2012)

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