CAS 19879-30-2|Bavachinin
| Common Name | Bavachinin | ||
|---|---|---|---|
| CAS Number | 19879-30-2 | Molecular Weight | 338.397 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 537.1±50.0 °C at 760 mmHg |
| Molecular Formula | C21H22O4 | Melting Point | 139-145ºC |
| MSDS | ChineseUSA | Flash Point | 190.3±23.6 °C |
| Symbol | GHS09 | Signal Word | Warning |
Names
| Name | 2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
|---|---|
| Synonym | More Synonyms |
Bavachinin BiologicalActivity
| Description | Bavachinin(7-O-Methylbavachin) is a natural compound isolated from the Chinese herb Fructus Psoraleae;has potent anti-angiogenic activity.IC50 value:Target:in vitro: Isobavachalcone significantly inhibits both oligomerization and fibrillization of Aβ42, whereas bavachinin inhibits fibrillization and leads to off-pathway aggregation. Both of the compounds attenuated Aβ42-induced toxicity in a SH-SY5Y cell model [1]. Bavachinin, has potent anti-angiogenic activity in vitro and in vivo. Bavachinin inhibited increases in HIF-1α activity in human KB carcinoma (HeLa cell derivative) and human HOS osteosarcoma cells under hypoxia in a concentration-dependent manner, probably by enhancing the interaction between von Hippel-Lindau (VHL) and HIF-1α [2].in vivo: significantly inhibited Th2 cytokine production, including IL-4, IL-5 and IL-13. Notably, this compound almost completely blocked inflammation in the ovalbumin (OVA)-sensitized animal asthma model [3]. |
|---|---|
| Related Catalog | Signaling Pathways >>Others >>OthersNatural Products >>FlavonoidsResearch Areas >>Inflammation/Immunology |
| References | [1]. Chen X, et al. Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro. FEBS Lett. 2013 Sep 17;587(18):2930-5. [2]. Nepal M, et al. Anti-angiogenic and anti-tumor activity of Bavachinin by targeting hypoxia-inducible factor-1α. Eur J Pharmacol. 2012 Sep 15;691(1-3):28-37. [3]. Chen X, et al. Treatment of allergic inflammation and hyperresponsiveness by a simple compound, Bavachinin, isolated from Chinese herbs. Cell Mol Immunol. 2013 Nov;10(6):497-505. |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 537.1±50.0 °C at 760 mmHg |
| Melting Point | 139-145ºC |
| Molecular Formula | C21H22O4 |
| Molecular Weight | 338.397 |
| Flash Point | 190.3±23.6 °C |
| Exact Mass | 338.151794 |
| PSA | 55.76000 |
| LogP | 4.93 |
| Vapour Pressure | 0.0±1.5 mmHg at 25°C |
| Index of Refraction | 1.590 |
| InChIKey | VOCGSQHKPZSIKB-FQEVSTJZSA-N |
| SMILES | COc1cc2c(cc1CC=C(C)C)C(=O)CC(c1ccc(O)cc1)O2 |
| Storage condition | ?20°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD - Lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >1 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- INDRBA Indian Drugs. (Indian Drugs Manufacturers' Assoc., 102B, Poonam Chambers, Dr. A. B. Rd., Worli, Bombay 400 018, India) V.1- 1963- Volume(issue)/page/year: 29,662,1992
Safety Information
| Symbol | GHS09 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H410 |
| Precautionary Statements | P273-P501 |
| Hazard Codes | N |
| Risk Phrases | 50 |
| Safety Phrases | 61 |
| RIDADR | UN 3077 9 / PGIII |
Articles7
More Articles| Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation. Planta Med. 78(9) , 903-6, (2012) Inhibiting interleukin-6 (IL-6) has been postulated as an effective therapy in the pathogenesis of several inflammatory diseases. In this study, seven flavonoids were isolated from the methanol extrac... | |
| Antioxidative components of Psoralea corylifolia (Leguminosae). Phytother Res. 16(6) , 539-44, (2002) A meroterpene and four flavonoids were isolated from the seeds of Psoralea corylifolia as antioxidative components. Their structures were elucidated by spectral data and identified as bakuchiol (1), b... | |
| Development of a fully automated on-line solid phase extraction and high-performance liquid chromatography with diode array detection method for the pharmacokinetic evaluation of bavachinin: a study on absolute bioavailability and dose proportionality. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 893-894 , 21-8, (2012) A fully automated on-line solid-phase extraction (SPE) and high-performance liquid chromatography (HPLC) with diode array detection (DAD) method was developed for determination of bavachinin in mouse ... |
Synonyms
| 2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-2,3-dihydro-4H-chromen-4-one |
| 2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-2,3-dihydro-4H-chromen-4-on |
| 2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one |
| 2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydro-4H-chromen-4-one |
| Bavachinin |
| 4H-1-Benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)- |
| 2-(4-Hydroxyphényl)-7-méthoxy-6-(3-méthyl-2-butèn-1-yl)-2,3-dihydro-4H-chromén-4-one |
| 7-O-Methylbavachin |
| 4'-Hydroxy-7-methoxy-6-(3-methyl-2-butenyl)flavanone |
| Bavachinin A |
