Bavachinin

Names

[ CAS No. ]:
19879-30-2

[ Name ]:
Bavachinin

[Synonym ]:
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

Biological Activity

[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 >> Others

Natural Products >> Flavonoids

Research 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.

[Related Small Molecules]

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

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ2981791

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl -2-butenyl)-, (S)-

CAS REGISTRY NUMBER :: 19879-30-2

BEILSTEIN REFERENCE NO. :: 3629340

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H22-O4

MOLECULAR WEIGHT :: 338.43

HEALTH HAZARD DATA

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

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 ...