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N-(beta-Oxooctan-1-oyl)homoserine lactone

HCID 127293
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
147795-39-9
Standard SMILES
CCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
InChIKey
FXCMGCFNLNFLSH-JTQLQIEISA-N
Molecular formula
C12H19NO4
Average molar mass
241.28 g/mol
Monoisotopic mass
241.13140809

Overview

3-Oxo-octanoic acid (2-oxo-tetrahydro-furan-3-YL)-amide has been reported in Azospirillum lipoferum with data available.

Names & identifiers

Preferred name
N-(beta-Oxooctan-1-oyl)homoserine lactone
IUPAC
3-oxo-N-[(3S)-2-oxooxolan-3-yl]octanamide
English name
N-(3-OXOOCTANOYL)-L-HOMOSERINE LACTONE
Molecular formula
C12H19NO4
Molecular weight
241.28

Names & synonyms

147795-39-9Aai-OOHLCF1, A. TumefaciensN-(beta-Ketooctanoyl)-L-hslN-(beta-Oxooctan-1-oyl)homoserine lactoneN-(beta-Oxooctan-1-oyl)-L-homoserine lactoneDTXSID60163802RefChem:504700DTXCID7086293N-3-oxo-octanoyl-L-Homoserine lactone3-oxo-N-[(3S)-2-oxooxolan-3-yl]octanamideN-(3-Oxooctanoyl)-L-homoserine lactone
Show more names
3-oxo-C8-HSLN-(β-Ketooctanoyl)-L-homoserineN-(3-Oxooctanoyl)-L-homoserine la(S)-3-oxo-N-(2-oxotetrahydrofuran-3-yl)octanaMide(S)-4-Oxo-N-(2-oxotetrahydrofuran-3-yl)nonanamideN-3-Oxo-octanoyl-L-homoserine lactone, 10 mM in DMSO
3-OXO-OCTANOIC ACID (2-OXO-TETRAHYDRO-FURAN-3-YL)-AMIDEN-(3-Oxooctanoyl)homoserine lactoneOctanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-MFCD08277025CHEMBL463321N-(3-oxo-octanoyl)-homoserine lactone3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]octanamideN-(3-Oxo-octanoyl)-L-homoserine lactone

Database identifiers

CAS
147795-39-9
PubChem CID
127293
DTXSID
DTXSID60163802
ChEMBL
CHEMBL463321
Nikkaji
J533.603A

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
72.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
7
Heavy atoms
17
Formal charge
0
Complexity
301

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> Fatty acyl homoserine lactones [FA0803]

Physicochemical properties

Melting point
54 · 54-60 °C
Boiling point
490.1 · 490.1±45.0 °C(Predicted)
Density
1.12 · 1.12±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
50 mg/mL, · chloroform: 50 mg/mL, clear, colorless
form
white powder
pka
11.09 · 11.09±0.46(Predicted)
color
White to off-white
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
SMILES
CCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
UNSPSC Code
12352202 · 12352202
NACRES
32 · NA.32
PPE
95 · Eyeshields, Gloves, type N95 (US)
WGK Germany
3 · 3
Storage Class
11 · 11 - Combustible Solids

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
Storage Class
11 - Combustible Solids

Chemistry & industry

Applications · 4 items

DescriptionQuorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. In the gram-negative bacterium A. tumefaciens, N-3-oxo-octanoyl-L-homoserine lactone promotes the expression of the transcriptional activator (and LuxR homolog) TraR.

UsesN-(3-Oxooctanoyl)-L-homoserine lactone has been used to study the effects of pH, temperature and salinity on extracellular polymeric substances (EPS) of Pseudomonas aeruginosa biofilm.

UsesN-3-oxo-octanoyl-L-Homoserine lactone is a reagent that promotes the expression of the transcriptional activator.

General DescriptionN-(3-Oxooctanoyl)-L-homoserine lactone is a common quorum sensing (QS) signal.

Suppliers46 total

湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Syntechem Co.,Ltd[email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
Shanghai Hanhong Scientific Co., Ltd.+undefined17612118332 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海谱科生物技术有限公司021-64705760 18027310741 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
沧州恩科医药科技有限公司0317-5296180 15533709196 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 19370895928 · [email protected]
沧州恩科医药科技有限公司0317-5106596 15533709196 · [email protected]
郑州艾克姆化工有限公司0371-63315541 13323832564 · [email protected]
北京迈瑞达科技有限公司010-82387566 18001021521 · [email protected]
上海右肯医药科技有限公司021-37910267 15821801668 · [email protected]
Aladdin Scientific[email protected]
江苏洪珉药业有限公司18221292452 · [email protected]
河南伊诺凯新材料有限公司15565215982 15565215982 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海迈瑞尔生化科技有限公司18621169109 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
河北品科研生物科技有限公司4000-685-696 18932660197 · [email protected]
上海甄准生物科技有限公司18019219489 18901678489 · [email protected]
资川生化科技(苏州)有限公司0512-66317708 13372112871 · [email protected]
Henan Fengda Chemical Co., Ltd+86-371-86557731 +86-13613820652 · [email protected]
湖南汇百益新材料有限公司0745-2866551 19976851779 · [email protected]
河南威梯希化工科技有限公司0371-55135753 18003832934 · [email protected]
广州优南科技有限公司020-82000279 18988941452 · [email protected]
武汉艾美捷科技有限公司4006800868;027-59626688 18771149750 · [email protected]

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes