 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C12H12O4 |
| Molecular Weight | 220.221 |
| Exact Mass | 220.073 |
| CAS # | 173933-40-9 |
| PubChem CID | 10082188 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 477.2±45.0 °C at 760 mmHg |
| Flash Point | 256.5±25.2 °C |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.666 |
| LogP | 0.7 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 16 |
| Complexity | 306 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CC(=O)/C=C(/C=C/C1=CC(=C(C=C1)O)O)\O |
| InChi Key | QDVIEIMMEUCFMW-QXYPORFMSA-N |
| InChi Code | InChI=1S/C12H12O4/c1-8(13)6-10(14)4-2-9-3-5-11(15)12(16)7-9/h2-7,14-16H,1H3/b4-2+,10-6- |
| Chemical Name | (3Z,5E)-6-(3,4-dihydroxyphenyl)-4-hydroxyhexa-3,5-dien-2-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 | Hispolon (at 25 and 50 μM, for 24 to 72 hours) reduces U87MG cell viability [2]. In U87MG cells, hispolon (25 and 50 μM, 24 and 48 hours) can cause apoptosis and G2/M cell cycle arrest [2]. Hispolon (25 and 50 μM, 2-8 hours) boosts the expression of the CDK inhibitor p21 but decreases the expression of the G1-S transition-related protein cyclin D4 [2]. The migration of U87MG cells is inhibited by hispolon (at 25 and 50 μM, for 24 hours) [2]. |
| ln Vivo | Hispolon (2.5-10 mg/kg, intraperitoneal injection) can decrease LPS-induced acute lung damage in mice [3]. Hispolon (5 and 10 mg/kg, subcutaneous injection) inhibits tumor growth in DBTRG xenograft mice [4]. |
| Cell Assay |
Cell Viability Assay[2] Cell Types: U87MG Cell Tested Concentrations: 25 and 50 μM Incubation Duration: 24, 48, 72 hrs (hours) Experimental Results: Inhibition of cell viability in a dose- and time-dependent manner. Western Blot Analysis [2] Cell Types: U87MG Cell Tested Concentrations: 25 and 50 μM Incubation Duration: 2, 4, 8 h Experimental Results: cyclin D4 levels diminished and p21 levels increased. |
| Animal Protocol |
Animal/Disease Models: LPS-induced acute lung injury in mice [3] Doses: 2.5, 5 and 10 mg/kg Route of Administration: intraperitoneal (ip) injection Experimental Results: Reduce the pathological effects of LPS-challenged mice. Decreases W/D ratio and MPO activity in the lungs. The production of pro-inflammatory cytokines is diminished. Animal/Disease Models: DBTRG xenograft mice [4] Doses: 5 and 10 mg/kg Route of Administration: subcutaneous injection Experimental Results: tumor volume reduction (RTV). HE and ki-67 staining inhibited GBM cell proliferation in vivo. |
| References |
[1]. Hispolon: A natural polyphenol and emerging cancer killer by multiple cellular signaling pathways. Environ Res. 2020 Nov;190:110017. [2]. Effects of hispolon on glioblastoma cell growth. Environ Toxicol. 2017 Sep;32(9):2113-2123. [3]. Attenuation of Lipopolysaccharide-Induced Acute Lung Injury by Hispolon in Mice, Through Regulating the TLR4/PI3K/Akt/mTOR and Keap1/Nrf2/HO-1 Pathways, and Suppressing Oxidative Stress-Mediated ER Stress-Induced Apoptosis and Autophagy. Nutrients. 2020 Jun 10;12(6):1742. [4]. Hispolon Induces Apoptosis, Suppresses Migration and Invasion of Glioblastoma Cells and Inhibits GBM Xenograft Tumor Growth In Vivo. Molecules. 2021 Jul 26;26(15):4497. |
| Additional Infomation |
Hispolon is a member of catechols. Hispolon has been reported in Tropicoporus linteus, Phellinus igniarius, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~125 mg/mL (~567.61 mM () |
| 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 | 4.5409 mL | 22.7046 mL | 45.4091 mL | |
| 5 mM | 0.9082 mL | 4.5409 mL | 9.0818 mL | |
| 10 mM | 0.4541 mL | 2.2705 mL | 4.5409 mL |