Bavachin | CAS# 19879-32-4 | Flavonoid

MedKoo Cat#: 574579 | Name: Bavachin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bavachin is a phytoestrogen that activates the estrogen receptors ERα and ERβ. Bavachin Protects Human Aortic Smooth Muscle Cells Against β-Glycerophosphate-Mediated Vascular Calcification and Apoptosis via Activation of mTOR-Dependent Autophagy and Suppression of β-Catenin Signaling.

Chemical Structure

Bavachin

CAS#19879-32-4

Theoretical Analysis

MedKoo Cat#: 574579

Name: Bavachin

CAS#: 19879-32-4

Chemical Formula: C20H20O4

Exact Mass: 324.1362

Molecular Weight: 324.37

Elemental Analysis: C, 74.06; H, 6.22; O, 19.73

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 550.00	2 Weeks
100mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Bavachin; Corylifolin

IUPAC/Chemical Name

(2S)-2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one

InChi Key

OAUREGNZECGNQS-IBGZPJMESA-N

InChi Code

InChI=1S/C20H20O4/c1-12(2)3-4-14-9-16-18(23)11-19(24-20(16)10-17(14)22)13-5-7-15(21)8-6-13/h3,5-10,19,21-22H,4,11H2,1-2H3/t19-/m0/s1

SMILES Code

O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(O)=C(C/C=C(C)\C)C=C13

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bavachin activates the estrogen receptors ERα and ERβ with EC50s of 320 and 680 nM, respectively.

In vitro activity:

Apoptosis and caspase activities were increased by bavachin in placental choriocarcinoma cells. Bavachin altered metabolic phenotypes by regulating electron transport chain complex and OXPHOS to suppress choriocarcinoma cell proliferation. It also led to calcium disruption and endoplasmic reticulum stress accompanied by mitochondrial membrane potential depolarization. It showed synergistic anti-cancer effects with paclitaxel on placental choriocarcinoma cells. Taken together, these results suggest that bavachin has therapeutic potential against placental choriocarcinoma and may be used to counter paclitaxel-induced toxicity. Reference: Free Radic Biol Med. 2020 Aug 20;156:26-35. https://www.sciencedirect.com/science/article/abs/pii/S0891584920310789?via%3Dihub

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	64.7	199.37
	DMF	50.0	154.14
	DMF:PBS (pH 7.2) (1:3)	0.3	0.77
	Ethanol	32.5	100.19

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 324.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Hung YL, Wang SC, Suzuki K, Fang SH, Chen CS, Cheng WC, Su CC, Yeh HC, Tu HP, Liu PL, Huang MY, Li CY. Bavachin attenuates LPS-induced inflammatory response and inhibits the activation of NLRP3 inflammasome in macrophages. Phytomedicine. 2019 Jun;59:152785. doi: 10.1016/j.phymed.2018.12.008. Epub 2018 Dec 10. PMID: 31009850. 2. Lee JY, Lim W, Song G. Bavachin suppresses human placental choriocarcinoma cells by targeting electron transport chain complexes and mitochondrial dysfunction. Free Radic Biol Med. 2020 Aug 20;156:26-35. doi: 10.1016/j.freeradbiomed.2020.05.022. Epub 2020 Jun 5. PMID: 32505737.

In vitro protocol:

In vivo protocol:

TBD

1: Luo Y, Gao X, Zou L, Lei M, Feng J, Hu Z. Bavachin Induces Ferroptosis through the STAT3/P53/SLC7A11 Axis in Osteosarcoma Cells. Oxid Med Cell Longev. 2021 Oct 18;2021:1783485. doi: 10.1155/2021/1783485. PMID: 34707773; PMCID: PMC8545544. 2: Qin N, Xu G, Wang Y, Zhan X, Gao Y, Wang Z, Fu S, Shi W, Hou X, Wang C, Li R, Liu Y, Wang J, Zhao H, Xiao X, Bai Z. Bavachin enhances NLRP3 inflammasome activation induced by ATP or nigericin and causes idiosyncratic hepatotoxicity. Front Med. 2021 Aug;15(4):594-607. doi: 10.1007/s11684-020-0809-2. Epub 2021 Apr 28. PMID: 33909257. 3: Wang Y, Yang Z, Wang Q, Ren Y, Wang Q, Li Z. Bavachin exerted anti- neuroinflammatory effects by regulation of A20 ubiquitin-editing complex. Int Immunopharmacol. 2021 Nov;100:108085. doi: 10.1016/j.intimp.2021.108085. Epub 2021 Aug 25. PMID: 34454289. 4: Jin YH, Kim DE, Jang MS, Min JS, Kwon S. Bavachin produces immunoadjuvant activity by targeting the NFAT signaling pathway. Phytomedicine. 2021 Dec;93:153796. doi: 10.1016/j.phymed.2021.153796. Epub 2021 Oct 9. PMID: 34689117. 5: Tao Y, Sun D, Ren X, Zhao Y, Zhang H, Jiang T, Guan J, Tang Y, Song W, Li S, Wang L. Bavachin Suppresses Alpha-Hemolysin Expression and Protects Mice from Pneumonia Infection by Staphylococcus aureus. J Microbiol Biotechnol. 2022 Oct 28;32(10):1253-1261. doi: 10.4014/jmb.2207.07048. Epub 2022 Sep 14. PMID: 36224757; PMCID: PMC9668093. 6: Wei X, Lin L, Yuan QQ, Wang XY, Zhang Q, Zhang XM, Tang KC, Guo MY, Dong TY, Han W, Huang DK, Qi YL, Zhang M, Zhang HB. Bavachin protects against diet- induced hepatic steatosis and obesity in mice. Acta Pharmacol Sin. 2023 Jan 31. doi: 10.1038/s41401-023-01056-z. Epub ahead of print. PMID: 36721007. 7: Lee JY, Lim W, Song G. Bavachin suppresses human placental choriocarcinoma cells by targeting electron transport chain complexes and mitochondrial dysfunction. Free Radic Biol Med. 2020 Aug 20;156:26-35. doi: 10.1016/j.freeradbiomed.2020.05.022. Epub 2020 Jun 5. PMID: 32505737. 8: Liang Z, Luo Z, Chen J, Li B, Li L, Shen C. Bavachin inhibits IL-4 expression by downregulating STAT6 phosphorylation and GATA-3 expression and ameliorates asthma inflammation in an animal model. Immunobiology. 2022 Mar;227(2):152182. doi: 10.1016/j.imbio.2022.152182. Epub 2022 Feb 3. PMID: 35134627. 9: Wang M, Tian B, Shen J, Xu S, Liu C, Guan L, Guo M, Dou J. Bavachin induces apoptosis in colorectal cancer cells through Gadd45a via the MAPK signaling pathway. Chin J Nat Med. 2023 Jan;21(1):36-46. doi: 10.1016/S1875-5364(23)60383-8. PMID: 36641231. 10: Yang Y, Tang X, Hao F, Ma Z, Wang Y, Wang L, Gao Y. Bavachin Induces Apoptosis through Mitochondrial Regulated ER Stress Pathway in HepG2 Cells. Biol Pharm Bull. 2018 Feb 1;41(2):198-207. doi: 10.1248/bpb.b17-00672. Epub 2017 Nov 29. PMID: 29187671. 11: Hung YL, Wang SC, Suzuki K, Fang SH, Chen CS, Cheng WC, Su CC, Yeh HC, Tu HP, Liu PL, Huang MY, Li CY. Bavachin attenuates LPS-induced inflammatory response and inhibits the activation of NLRP3 inflammasome in macrophages. Phytomedicine. 2019 Jun;59:152785. doi: 10.1016/j.phymed.2018.12.008. Epub 2018 Dec 10. PMID: 31009850. 12: Park J, Seo E, Jun HS. Bavachin alleviates diabetic nephropathy in db/db mice by inhibition of oxidative stress and improvement of mitochondria function. Biomed Pharmacother. 2023 May;161:114479. doi: 10.1016/j.biopha.2023.114479. Epub 2023 Mar 13. PMID: 36921531. 13: Lee H, Li H, Noh M, Ryu JH. Bavachin from Psoralea corylifolia Improves Insulin-Dependent Glucose Uptake through Insulin Signaling and AMPK Activation in 3T3-L1 Adipocytes. Int J Mol Sci. 2016 Apr 8;17(4):527. doi: 10.3390/ijms17040527. PMID: 27070585; PMCID: PMC4848983. 14: Takeda T, Tsubaki M, Tomonari Y, Kawashima K, Itoh T, Imano M, Satou T, Nishida S. Bavachin induces the apoptosis of multiple myeloma cell lines by inhibiting the activation of nuclear factor kappa B and signal transducer and activator of transcription 3. Biomed Pharmacother. 2018 Apr;100:486-494. doi: 10.1016/j.biopha.2018.02.019. Epub 2018 Feb 23. PMID: 29477912. 15: Wang JH, Pei YY, Xu HD, Li LJ, Wang YQ, Liu GL, Qu Y, Zhang N. Effects of bavachin and its regulation of melanin synthesis in A375 cells. Biomed Rep. 2016 Jul;5(1):87-92. doi: 10.3892/br.2016.688. Epub 2016 May 20. PMID: 27347410; PMCID: PMC4906567. 16: Ni YH, Deng HF, Zhou L, Huang CS, Wang NN, Yue LX, Li GF, Yu HJ, Zhou W, Gao Y. Ginsenoside Rb1 Ameliorated Bavachin-Induced Renal Fibrosis via Suppressing Bip/eIF2α/CHOP Signaling-Mediated EMT. Front Pharmacol. 2022 Jul 8;13:872474. doi: 10.3389/fphar.2022.872474. PMID: 35873571; PMCID: PMC9304982. 17: Yeon MH, Seo E, Lee JH, Jun HS. Bavachin and Corylifol A Improve Muscle Atrophy by Enhancing Mitochondria Quality Control in Type 2 Diabetic Mice. Antioxidants (Basel). 2023 Jan 6;12(1):137. doi: 10.3390/antiox12010137. PMID: 36671000; PMCID: PMC9855061. 18: Zhang J, Liu L, Li H, Zhang B. Pharmacokinetic study on the interaction between pachymic acid and bavachin and its potential mechanism. Pharm Biol. 2021 Dec;59(1):1256-1259. doi: 10.1080/13880209.2021.1942924. PMID: 34517743; PMCID: PMC8439242. 19: Ban KY, Nam GY, Kim D, Oh YS, Jun HS. Prevention of LPS-Induced Acute Kidney Injury in Mice by Bavachin and Its Potential Mechanisms. Antioxidants (Basel). 2022 Oct 24;11(11):2096. doi: 10.3390/antiox11112096. PMID: 36358467; PMCID: PMC9686515. 20: He HQ, Law BYK, Zhang N, Qiu CL, Qu YQ, Wu AG, Han Y, Song Q, Zheng WL, Liu Y, He YZ, Wong VKW. Bavachin Protects Human Aortic Smooth Muscle Cells Against β-Glycerophosphate-Mediated Vascular Calcification and Apoptosis via Activation of mTOR-Dependent Autophagy and Suppression of β-Catenin Signaling. Front Pharmacol. 2019 Dec 19;10:1427. doi: 10.3389/fphar.2019.01427. PMID: 31920640; PMCID: PMC6930901.