| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
Purity: ≥98%
| Targets |
Hirsutanone targets multiple cellular signaling proteins, including PI3K, ERK1, Akt, EGFR, and NF-κB. It binds directly to PI3K and ERK1 in a non-ATP competitive manner, inhibiting their kinase activities. By inhibiting PI3K, it also affects downstream signaling through the PI3K/Akt/mTOR pathway. Hirsutanone's ability to target multiple key signaling nodes contributes to its diverse biological effects. It also exhibits potent antioxidant activity. Its interaction with these targets is responsible for its anti-inflammatory, anti-tumor, and anti-adipogenic activities.
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| ln Vitro |
In 3T3-L1 preadipocytes, hirsutenone (0-100 μM; 48 hours) suppresses adipogenesis and, at 20-100 μM, shows little toxicity [1]. In 3T3-L1 preadipocytes, hirsutenone (0-100 μM; 48 hours) attenuates lipid accumulation produced by MDI in a dose-dependent manner. Specifically, in 3T3-L1 preadipocytes, 40 and 80 μM HST markedly inhibited MDI-induced adipogenesis [1]. In 3T3-L1 preadipocytes, hirsutenone (0-100 μM; 48 hours) dose-dependently lowers the levels of PPARg, C/EBPα, and FAS protein expression [1]. Cell cycle entry into the S and G2/M phases, which happens at 20 hours as opposed to 20 hours, is inhibited by hirsutenone (80 μM; 20-24 hours). At 24 hours, more cells (53% of total cells) were arrested in the G1 phase as opposed to the MDI-induced group, where the majority of cells (56% of total cells) were in the G2/M phase [1].
In vitro, Hirsutanone demonstrates significant biological activity in various cell-based assays. In 3T3-L1 preadipocytes, it suppresses adipogenesis in a dose-dependent manner at concentrations of 0-100 μM. Specifically, 40 and 80 μM Hirsutanone markedly inhibit MDI-induced adipogenesis. It dose-dependently lowers the levels of key adipogenic proteins, including PPARγ, C/EBPα, and FAS. Hirsutanone (80 μM) inhibits cell cycle entry into the S and G2/M phases, causing cell cycle arrest in the G1 phase. At concentrations of 20-100 μM, it shows little toxicity in 3T3-L1 cells. |
| ln Vivo |
In vivo data for Hirsutanone are limited in the available literature. Based on its in vitro mechanism of action, the compound has potential for in vivo efficacy in models of obesity, cancer, and inflammation. Its ability to attenuate adipogenesis by targeting PI3K and ERK suggests that it could be effective in preventing or treating obesity. However, specific in vivo efficacy data, including animal models, dosing regimens, and pharmacokinetic-pharmacodynamic relationships, are not detailed in the available sources.
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| Enzyme Assay |
In vitro enzyme assays for Hirsutanone typically involve measuring its inhibitory activity against its target kinases, PI3K and ERK1. Kinase assays are performed using recombinant PI3K or ERK1 enzymes and appropriate substrates. The compound is incubated with the enzyme and substrate in the presence of ATP, and the phosphorylation of the substrate is measured. The IC50 for inhibition is determined by measuring enzyme activity at various concentrations of Hirsutanone. The non-ATP competitive nature of its binding can be confirmed by performing the assay at different ATP concentrations.
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| Cell Assay |
Cellular assays for Hirsutanone are performed in various cell lines, most notably in 3T3-L1 preadipocytes to study its anti-adipogenic effects. Cells are differentiated into adipocytes using a standard differentiation cocktail (MDI: methylisobutylxanthine, dexamethasone, insulin) in the presence or absence of Hirsutanone. After differentiation, lipid accumulation is assessed by Oil Red O staining. The expression of adipogenic marker proteins such as PPARγ, C/EBPα, and FAS is measured by Western blotting. Cell cycle analysis is performed by flow cytometry.
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| Animal Protocol |
In vivo animal studies with Hirsutanone are not extensively documented in the available literature. Based on its anti-adipogenic and anti-tumor activities, potential in vivo models could include high-fat diet-induced obesity models in mice or xenograft models for cancer. In such studies, Hirsutanone would be administered orally or intraperitoneally, and endpoints would include body weight, fat mass, tumor growth, and molecular markers of adipogenesis or tumor progression. However, specific protocols are not detailed in the available sources.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for Hirsutanone are not extensively reported. The compound is a diarylheptanoid with a molecular weight of 328.36. It has a density of 1.3±0.1 g/cm³ and a LogP of 2.16, indicating moderate lipophilicity. The compound is stable when stored as a powder at -20°C for up to 3 years. However, detailed pharmacokinetic parameters such as absorption, distribution, metabolism, excretion, half-life, and bioavailability are not available in the literature for this natural product.
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| Toxicity/Toxicokinetics |
Hirsutanone shows little toxicity in 3T3-L1 preadipocytes at concentrations of 20-100 μM. However, comprehensive toxicology data for this compound are not extensively reported. As a natural product with multiple biological activities, it may have off-target effects or toxicity at higher concentrations. The compound is classified as a research-use-only chemical and is not intended for human consumption. Specific toxicological data, including acute toxicity, genotoxicity, and target organ effects, are not reported in the available literature.
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| References | |
| Additional Infomation |
(4E)-1,7-bis(3,4-dihydroxyphenyl)hepten-4-en-3-one is a diarylheptane compound. It has been reported that tuftenones exist in alder, Japanese alder, and other organisms with relevant data.
Hirsutanone is a research-grade natural product not approved for clinical use. Its primary application is as a pharmacological tool for studying the roles of PI3K and ERK in adipogenesis, inflammation, and cancer. The compound is of interest for its potential therapeutic applications in obesity, cancer, and inflammatory diseases. Its non-ATP competitive binding to PI3K and ERK makes it a unique tool for studying kinase signaling. |
| Molecular Formula |
C19H20O5
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|---|---|
| Molecular Weight |
328.3591
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| Exact Mass |
328.131
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| CAS # |
41137-87-5
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| PubChem CID |
637394
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| Appearance |
Off-white to light brown ointment
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
622.0±55.0 °C at 760 mmHg
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| Flash Point |
344.0±28.0 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.649
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| LogP |
2.16
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
24
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| Complexity |
422
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(/C=C/CCC1=CC=C(O)C(O)=C1)CCC2=CC=C(O)C(O)=C2
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| InChi Key |
VWHYFMQKJYFLCC-DUXPYHPUSA-N
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| InChi Code |
InChI=1S/C19H20O5/c20-15(8-5-14-7-10-17(22)19(24)12-14)4-2-1-3-13-6-9-16(21)18(23)11-13/h2,4,6-7,9-12,21-24H,1,3,5,8H2/b4-2+
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| Chemical Name |
(E)-1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0454 mL | 15.2272 mL | 30.4544 mL | |
| 5 mM | 0.6091 mL | 3.0454 mL | 6.0909 mL | |
| 10 mM | 0.3045 mL | 1.5227 mL | 3.0454 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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