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  4. 2-Undecanone

2-Undecanone is an orally active organic ketone. 2-Undecanone exerts antibacterial effects by inhibiting bacterial chaperone systems and interfering with the refolding of heat-inactivated proteins. 2-Undecanone also ameliorates asthmatic inflammation and airway remodeling by blocking the NF-κB pathway, and activates the Nrf2 pathway to reduce oxidative damage and prevent lung cancer induced by Benzo[a]pyrene (HY-107377). 2-Undecanone can be used in research related to cancer, asthma and infections.

For research use only. We do not sell to patients.

2-Undecanone

2-Undecanone Chemical Structure

CAS No. : 112-12-9

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Liquid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO
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Based on 1 publication(s) in Google Scholar

Other Forms of 2-Undecanone:

2-Undecanone Related Antibodies

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  • Biological Activity

  • Purity & Documentation

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  • Customer Review

Description

2-Undecanone is an orally active organic ketone. 2-Undecanone exerts antibacterial effects by inhibiting bacterial chaperone systems and interfering with the refolding of heat-inactivated proteins. 2-Undecanone also ameliorates asthmatic inflammation and airway remodeling by blocking the NF-κB pathway, and activates the Nrf2 pathway to reduce oxidative damage and prevent lung cancer induced by Benzo[a]pyrene (HY-107377). 2-Undecanone can be used in research related to cancer, asthma and infections[1][2][3].

IC50 & Target

Human Endogenous Metabolite

 

In Vitro

2-Undecanone (6.25-200 μM; 48 h) exhibits low intrinsic cytotoxicity toward BEAS-2B cells, and reverses Benzo[a]pyrene (B[a]P) (HY-107377)-induced cytotoxicity in a dose-dependent manner[1].
2-Undecanone (25-100 μM; 48 h) dose-dependently reverses B[a]P-induced G0/G1 cell cycle arrest in BEAS-2B cells and restores the expression of cyclin D1[1].
2-Undecanone (25-100 μM; 48 h) reduces B[a]P-induced DNA strand breaks in BEAS-2B cells[1].
2-Undecanone (25-100 μM; 48 h) dose-dependently reduces B[a]P-induced overexpression of p-H2A.X in BEAS-2B cells, indicating that it can alleviate DNA double-strand breaks[1].
2-Undecanone (25-100 μM; 24 h) dose-dependently reduces B[a]P-induced overexpression of IL-1β and pro-IL-1β in BEAS-2B cells, indicating that it inhibits inflammatory responses[1].
2-Undecanone (25-100 μM; 48 h) reduces the excessive intracellular ROS production induced by B[a]P in BEAS-2B cells[1].
2-Undecanone (50 μM) activates the Nrf2-HO-1/NQO-1 signaling pathway in BEAS-2B cells and reverses the inhibitory effect of B[a]P on this pathway in BEAS-2B cells[1].
2-Undecanone (50 μM; 24-48 h) exerts protective effects against B[a]P-induced cytotoxicity, excessive ROS production and DNA damage in BEAS-2B cells via the Nrf2-HO-1/NQO-1 signaling pathway[1].
2-Undecanone (20 μmol; 0-90 min) almost completely inhibits the DnaK-ClpB-dependent refolding of heat-inactivated Photobacterium leiognathi luciferase in cell lysates of Escherichia coli JW3663 ibpB::kan (pLeo1)[2].
2-Undecanone (12.5-50 μM; 48 h) inhibits PDGF-BB-induced proliferation of primary mouse airway smooth muscle cells in a dose-dependent manner when co-incubated with 20 ng/mL PDGF-BB[3].
2-Undecanone (12.5-50 μM; 48 h) dose-dependently attenuates PDGF-BB-induced migration of primary mouse airway smooth muscle cells pretreated with 20 ng/mL PDGF-BB[3].
When co-incubated with 20 ng/mL PDGF-BB, 2-Undecanone (12.5-50 μM; 48 h) dose-dependently reverses PDGF-BB-induced phenotypic switch of primary mouse airway smooth muscle cells from the contractile to the synthetic phenotype, restores calmodulin expression and reduces osteopontin expression[3].
2-Undecanone (12.5-50 μM; 48 h) inhibits PDGF-BB-induced secretion of the proinflammatory cytokines IL-6 and TNF-α from primary mouse airway smooth muscle cells in a dose-dependent manner[3].
2-Undecanone (50 μM; 48 h) inhibits PDGF-BB-induced activation of the NF-κB pathway in primary mouse airway smooth muscle cells during co-incubation with 20 ng/mL PDGF-BB, reduces the phosphorylation levels of IκBα and NF-κB p65, and blocks the nuclear translocation of NF-κB p65[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

2-Undecanone Related Antibodies

Cell Cytotoxicity Assay[1]

Cell Line: BEAS-2B human lung epithelial cells
Concentration: 6.25, 12.5, 25, 50, 100 and 200 μM
Incubation Time: 48 h
Result: Did not change or weakly decreased BEAS-2B cell viability when used alone at 6.25-200 μM for 48 h.
Effectively increased cell viability in a dose-dependent manner when cotreated with 5 μM B[a]P at 6.25-200 μM for 48 h.

Cell Cycle Analysis[1]

Cell Line: BEAS-2B human lung epithelial cells
Concentration: 25, 50, 100 μM
Incubation Time: 48 h
Result: Significantly decreased the percentage of cells in G0/G1 phase and reversed the suppression of cyclin D1 protein levels in a dose-dependent manner.

Western Blot Analysis[1]

Cell Line: BEAS-2B human lung epithelial cells
Concentration: 25, 50, 100 μM
Incubation Time: 24 h
Result: Significantly decreased B[a]P-induced increases in IL-1β protein levels in culture supernatants, and pro-IL-1β and IL-1β protein levels in cell lysates, in a dose-dependent manner (p < 0.001) when cotreated with 5 μM B[a]P at 25, 50, or 100 μM for 24 h compared with B[a]P treatment alone.
In Vivo

2-Undecanone (100-200 mg/kg; p.o.; five times weekly; 38 weeks) significantly inhibits B[a]P-induced lung tumorigenesis in A/J mice with tumor inhibition rates of 33.62 ± 14.60% and 38.26 ± 13.59%, respectively, while also reducing DNA damage and systemic inflammation[1].
2-Undecanone (100-400 mg/kg; i.g.; once daily; 7 days) dose-dependently alleviates OVA-induced asthma in female BALB/c mice by reducing airway inflammation, histopathological lung changes, and activation of the NF-κB pathway[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: A/J mice (male, 4-6 weeks old, 18-22 g, intraperitoneal injection of 100 mg/kg benzo(a)pyrene to induce lung adenocarcinoma)[1]
Dosage: 100 mg/kg; 200 mg/kg
Administration: p.o.; five times weekly; 38 weeks
Result: Reduced visible lung tumor numbers.
Downregulated phosphorylated H2A.X (p-H2A.X) protein levels in mouse lung tissue.
Reduced plasma interleukin-1β (IL-1β) levels.
Showed no significant differences in body weight or organ indexes (heart, liver, spleen, kidney, thymus) compared to control mice.
Animal Model: BALB/c (female, 6 weeks old, 18-22 g, OVA-induced allergic airway inflammation)[3]
Dosage: 100 mg/kg; 200 mg/kg; 400 mg/kg
Administration: i.g.; once daily; 7 days
Result: Reduced OVA-induced inflammatory cell infiltration with dose-dependent reduction in lung inflammation scores, goblet cell hyperplasia with dose-dependent reduction in PAS-positive cell counts, and airway smooth muscle thickness with dose-dependent reduction in α-SMA-positive staining and smooth muscle thickness measurements in lung tissues.
Dose-dependently reduced total inflammatory cell counts, eosinophil counts, neutrophil counts, lymphocyte counts, and macrophage counts in BALF.
Dose-dependently decreased BALF levels of IL-4, IL-5, and IL-13, as well as OVA-specific IgE levels in both BALF and serum.
Inhibited OVA-induced phosphorylation of IκBα and NF-κB p65, and reduced nuclear translocation of NF-κB p65 in lung tissues (400 mg/kg dose).
Molecular Weight

170.30

Formula

C11H22O
CAS No.
Appearance

Liquid (Density: 0.825  g/cm3  )

Color

Colorless to light yellow

SMILES

CC(CCCCCCCCC)=O
Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Store at room temperature, keep dry and cool

In solvent -80°C 1 year
-20°C 6 months
Solvent & Solubility
In Vitro: 

DMSO : 100 mg/mL (587.20 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 5.8720 mL 29.3600 mL 58.7199 mL
5 mM 1.1744 mL 5.8720 mL 11.7440 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.5 mg/mL (14.68 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.5 mg/mL (14.68 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.90%

SDS (458 KB)

COA (239 KB) HNMR (235 KB) MS (70 KB) GC (286 KB)

Handling Instructions (2659 KB)
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 5.8720 mL 29.3600 mL 58.7199 mL 146.7998 mL
5 mM 1.1744 mL 5.8720 mL 11.7440 mL 29.3600 mL
10 mM 0.5872 mL 2.9360 mL 5.8720 mL 14.6800 mL
15 mM 0.3915 mL 1.9573 mL 3.9147 mL 9.7867 mL
20 mM 0.2936 mL 1.4680 mL 2.9360 mL 7.3400 mL
25 mM 0.2349 mL 1.1744 mL 2.3488 mL 5.8720 mL
30 mM 0.1957 mL 0.9787 mL 1.9573 mL 4.8933 mL
40 mM 0.1468 mL 0.7340 mL 1.4680 mL 3.6700 mL
50 mM 0.1174 mL 0.5872 mL 1.1744 mL 2.9360 mL
60 mM 0.0979 mL 0.4893 mL 0.9787 mL 2.4467 mL
80 mM 0.0734 mL 0.3670 mL 0.7340 mL 1.8350 mL
100 mM 0.0587 mL 0.2936 mL 0.5872 mL 1.4680 mL
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2-Undecanone Related Classifications

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  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

2-Undecanone112-12-9Keap1-Nrf2Interleukin RelatedNF-κBEnvironmental PollutantsBacterialILNuclear factor-κBNuclear factor-kappaBEnvironmental ContaminantsNrf2NQO-1Escherichia coliA/J miceNF-κB p65BEAS-2B cellsB[a]PROSHO-1BALB/c miceInhibitorinhibitorinhibit

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