(S)-7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one
bavachin
CAS: 19879-32-4
Molecular Formula: C20H20O4
(S)-7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one - Names and Identifiers
(S)-7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one - Physico-chemical Properties
| Molecular Formula | C20H20O4 |
| Molar Mass | 324.37 |
| Density | 1.244 |
| Melting Point | 191-192°C |
| Boling Point | 558.3±50.0 °C(Predicted) |
| Specific Rotation(α) | (EtOH)-21.9 |
| Flash Point | 202.1°C |
| Solubility | Soluble in methanol, ethanol, DMSO and other organic solvents. |
| Vapor Presure | 4.52E-13mmHg at 25°C |
| Appearance | White crystalline powder |
| pKa | 8.27±0.40(Predicted) |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.621 |
| MDL | MFCD11617359 |
| Physical and Chemical Properties | Pale yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from psoralen PsoraleacorylifoliaLinn. The fruit. |
| In vitro study | Bavachin significantly inhibits melanin synthesis and TYR activity. Bavachin (10 µM) inhibits the expression of TYR and JNK proteins, and the expression of TYR, TRP-1, TRP-2, ERK1, ERK2 and JNK2 mRNA in A375 cells. ICI182780 and U0126 cAN significantly reverse the bavachin treatment on the protein expression levels and the mRNA expression of TYR, TRP-1, TRP-2, ERK1, ERK2 and JNK2. Bavachin accumulates lipid in a dose dependent manner in ORO staining experiments. Bavachin significantly increases the growth of preadipoctye at 10 µM compared with the control cells in MTT assay. Bavachin also increases BrdU incorporation into newly synthesized DNA during pre-adipocyte proliferation. BrdU incorporation is enhanced by insulin and further enhanced by co-treatment with insulin and bavachin at 2 and 10 µM. Bavachin activates adipogenic factors and increases PPARγ transcriptional activity in differentiated adipocytes. Bavachin enhances insulin-stimulated glucose uptake through GLUT4 translocation via Akt and AMPK pathway. BVN significantly increases both hMAO-A and hMAO-B activities. Bavachin shows ER ligand binding activity in competitive displacement of [ 3 H] E2 from recombinant ER. The estrogenic activity of bavachin is characterized in a transient transfection system using ERα or ERβ and estrogen-responsive luciferase plasmids in CV-1 cells with an EC 50 of 320 nM and 680 nM, respectively. Bavachin increases the mRNA levels of estrogen-responsive genes such as pS2 and PR, and decreases the protein level of ERα by proteasomal pathway. |
(S)-7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one - Reference
| Reference Show more | 1. Ding Liyan, Zhou Lu, Wang Lina, et al. Determination of Different Types of Components in Psoralea corylifolia by One Test and Multiple Evaluation Method [J]. 2013 19(5):152-154. 2. Liu Baojun, Yan Lili, Wang Jinfang, et al. Determination of Psoralea corylifolia in Cosmetics by High Performance Liquid Chromatography [J]. China Public Health 2012 28(007):990-991. 3. Huang Ting, guo Yanhua, Ding Liyan, et al. Effect of medicinal juice on its anti-OP chemical composition [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2013(05):62-64. 4. Huang Xiaojing, Zhou Xiao, Yongsheng. Simultaneous Determination of Psoralea dihydroflavone and Psoralen Phenol in Psoralea corylifolia L. by HPLC [J]. Chinese Pharmacy 2017(24). 5. Huang Xiaojing, zhou Xiaoying, Zhou Shiyu. Effect of Cobalt -60 Irradiation on Fingerprint of Psoralea corylifolia [J]. Chinese Drug Evaluation, 2015, 000(003):159-161. 6. Chen, Zhi-Jing, et al. "Dietary total prenylflavonoids from the fruits of Psoralea corylifolia L. prevents age-related cognitive deficits and down-regulates Alzheimer's markers in SAMP8 mICE." Molecules 23.1 (2018): 196.https://doi.org/10.3390/molecules230 7. [IF = 4.379] Li Kai et al. "Quantitative analysis, pharmacokinetics and metabolomics study for the comprehensive characterization of the salt-processing mechanism of Psoraleae Fructus." Sci Rep-Uk. 2019 Jan;9(1):1-10 8. [IF = 3.935] Tiehua Zhang et al. "Quantitative structure-activity relationship for estrogenic flavonoids from Psoralea corylifolia." J Pharmaceut Biomed. 2018 Nov;161:129 9. [IF = 3.267] Zhi-Jing Chen et al. "Dietary Total Prenylflavonoids from the Fruits of Psoralea corylifolia L. Prevents Age-Related Cognitive Deficits and Down-Regulates Alzheimer's Markers in SAMP8 Mice." Molecules. 2018 Jan;23(1): 196 10. [IF = 2.675] Xiumin Chen et al. "Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro." Febs Lett. 2013 Sep;587(18):2930-2935 |
(S)-7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one - Reference Information
| biological activity | Bavachin are flavonoids isolated from psoralea corylifolia seeds, which activate estrogen receptors ERα and ERβ as phytoestrogens, with EC50 values of 320 and 680 nM respectively. |
| target | IC50: 320 nM (ERα), 680 nM (ERβ) |
| in vitro study | Bavachin significantly inhibits melanin synthesis and TYR activity. Bavachin (10 µM) inhibits the expression of TYR and JNK proteins, and the expression of TYR, TRP-1, TRP-2, ERK1, ERK2 and JNK2 mRNA in A375 cells. ICI182780 and U0126 cAN significantly reverse the bavachin treatment on the protein expression levels and the mRNA expression of TYR, TRP-1, TRP-2, ERK1, ERK2 and JNK2. Bavachin accumulates lipid in a pose dependent manner in ORO staining experiments. Bavachin significantly increases the growth of preadipoctye at 10 m compared with the control cells in MTT assay. Bavachin also increases BrdU incorporation into nely synthesized DNA during pre-adipocyte proliferation. BrdU incorporation is enhanced by insulin and further enhanced by co-treatment with insulin and bavachin at 2 and 10 m. Bavachin activates adipogenic factors and increases PPAR γ transcriptional activity in differentiated adipocytes. Bavachin enhances insulin-stimulated glucose uptake through GLUT4 translocation via Akt and AMPK pathway. BVN significantly increases both hMAO-A and hMAO-B activities. Bavachin shows ER ligand binding activity in competitive displacement of [ 3 H] E2 from recombinant ER. The estrogenic activity of bavachin is characterized in a transient transfection system using ER α or ER β and estrogen-responsive luciferase plasmids in CV-1 cells with an EC 50 of 320 nM and 680 nM, respectively. Bavachin increases the mRNA levels of estrogen-responsive genes such as pS2 and PR, and decreases the protein level of ERαby proteasomal pathway. |
| chemical properties | light yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from psoralen PsoraleacorylifoliaLinn. The fruit. |
| use | psoralen a has the functions of dilating coronary arteries, enhancing myocardial contractility and increasing cardiac power. a plant estrogen can activate erα and erβ(EC50s are 320 nm and 680nm respectively), stimulate osteoblast proliferation and differentiation, and prevent bone loss after ovariectomy in rats. |
Last Update：2024-04-09 21:11:58
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Product Name: Bavachin Visit Supplier Webpage Request for quotationCAS: 19879-32-4
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: Bavachin Visit Supplier Webpage Request for quotationCAS: 19879-32-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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(S)-7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one
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