Hirsutanone is a bioactive diarylheptanoid found in Alnus species. It exhibits many biological activities, including anti-inflammatory, anti-tumor promoting and anti-atopic dermatitis effects. Hirsutenone attenuates adipogenesis by binding directly to PI3K and ERK1 in a non-ATP competitive manner. Hirsutenone can be used for the study of obesity.
Physicochemical Properties
| Molecular Formula | C19H20O5 |
| Molecular Weight | 328.3591 |
| Exact Mass | 328.131 |
| CAS # | 41137-87-5 |
| PubChem CID | 637394 |
| Appearance | Off-white to light brown ointment |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 622.0±55.0 °C at 760 mmHg |
| Flash Point | 344.0±28.0 °C |
| Vapour Pressure | 0.0±1.9 mmHg at 25°C |
| Index of Refraction | 1.649 |
| LogP | 2.16 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 24 |
| Complexity | 422 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(/C=C/CCC1=CC=C(O)C(O)=C1)CCC2=CC=C(O)C(O)=C2 |
| InChi Key | VWHYFMQKJYFLCC-DUXPYHPUSA-N |
| 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+ |
| Chemical Name | (E)-1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| 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]. |
| References |
[1]. Hirsutenone Directly Targets PI3K and ERK to Inhibit Adipogenesis in 3T3-L1 Preadipocytes.J Cell Biochem. |
| Additional Infomation |
(4E)-1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one is a diarylheptanoid. Hirsutenone has been reported in Alnus firma, Alnus japonica, and other organisms with data available. |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (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 |