Chrysoeriol | CAS# 491-71-4 | Methoxyflavonoid

MedKoo Cat#: 574628 | Name: Chrysoeriol

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Description:

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

Chrysoeriol is a methoxyflavonoid and metabolite of Luteolin that selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells.

Chemical Structure

Chrysoeriol

CAS#491-71-4

Theoretical Analysis

MedKoo Cat#: 574628

Name: Chrysoeriol

CAS#: 491-71-4

Chemical Formula: C16H12O6

Exact Mass: 300.0634

Molecular Weight: 300.27

Elemental Analysis: C, 64.00; H, 4.03; O, 31.97

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks
25mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Chrysoeriol; Chrysoriol; Chryseriol; 3'-Methoxyapigenin; Luteolin 3'-methyl ether;

IUPAC/Chemical Name

5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one

InChi Key

SCZVLDHREVKTSH-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3

SMILES Code

O=C1C=C(C2=CC=C(O)C(OC)=C2)OC3=CC(O)=CC(O)=C13

Appearance

Solid powder

Purity

>97% (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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 300.27 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

1: Aboulaghras S, Sahib N, Bakrim S, Benali T, Charfi S, Guaouguaou FE, Omari NE, Gallo M, Montesano D, Zengin G, Taghzouti K, Bouyahya A. Health Benefits and Pharmacological Aspects of Chrysoeriol. Pharmaceuticals (Basel). 2022 Aug 7;15(8):973. doi: 10.3390/ph15080973. PMID: 36015121; PMCID: PMC9415049. 2: Song J, Lee H, Heo H, Lee J, Kim Y. Effects of Chrysoeriol on Adipogenesis and Lipolysis in 3T3-L1 Adipocytes. Foods. 2022 Dec 30;12(1):172. doi: 10.3390/foods12010172. PMID: 36613388; PMCID: PMC9818938. 3: Wu JY, Chen YJ, Fu XQ, Li JK, Chou JY, Yin CL, Bai JX, Wu Y, Wang XQ, Li AS, Wong LY, Yu ZL. Chrysoeriol suppresses hyperproliferation of rheumatoid arthritis fibroblast-like synoviocytes and inhibits JAK2/STAT3 signaling. BMC Complement Med Ther. 2022 Mar 16;22(1):73. doi: 10.1186/s12906-022-03553-w. PMID: 35296317; PMCID: PMC8928618. 4: Limboonreung T, Tuchinda P, Chongthammakun S. Chrysoeriol mediates mitochondrial protection via PI3K/Akt pathway in MPP+ treated SH-SY5Y cells. Neurosci Lett. 2020 Jan 1;714:134545. doi: 10.1016/j.neulet.2019.134545. Epub 2019 Oct 14. PMID: 31622648. 5: Wu JY, Chen YJ, Bai L, Liu YX, Fu XQ, Zhu PL, Li JK, Chou JY, Yin CL, Wang YP, Bai JX, Wu Y, Wu ZZ, Yu ZL. Chrysoeriol ameliorates TPA-induced acute skin inflammation in mice and inhibits NF-κB and STAT3 pathways. Phytomedicine. 2020 Mar;68:153173. doi: 10.1016/j.phymed.2020.153173. Epub 2020 Jan 19. PMID: 31999977. 6: Yoon HS, Park CM. Chrysoeriol ameliorates COX-2 expression through NF-κB, AP-1 and MAPK regulation via the TLR4/MyD88 signaling pathway in LPS-stimulated murine macrophages. Exp Ther Med. 2021 Jul;22(1):718. doi: 10.3892/etm.2021.10150. Epub 2021 May 3. PMID: 34007327; PMCID: PMC8120564. 7: Ramirez G, Zamilpa A, Zavala M, Perez J, Morales D, Tortoriello J. Chrysoeriol and other polyphenols from Tecoma stans with lipase inhibitory activity. J Ethnopharmacol. 2016 Jun 5;185:1-8. doi: 10.1016/j.jep.2016.03.014. Epub 2016 Mar 10. PMID: 26970570. 8: Kim MH, Kwon SY, Woo SY, Seo WD, Kim DY. Antioxidative Effects of Chrysoeriol via Activation of the Nrf2 Signaling Pathway and Modulation of Mitochondrial Function. Molecules. 2021 Jan 9;26(2):313. doi: 10.3390/molecules26020313. PMID: 33435366; PMCID: PMC7826659. 9: Min DY, Jung E, Ahn SS, Lee YH, Lim Y, Shin SY. Chrysoeriol Prevents TNFα- Induced CYP19 Gene Expression via EGR-1 Downregulation in MCF7 Breast Cancer Cells. Int J Mol Sci. 2020 Oct 12;21(20):7523. doi: 10.3390/ijms21207523. PMID: 33053908; PMCID: PMC7588959. 10: Kim YH, Lee YS, Choi EM. Chrysoeriol isolated from Eurya cilliata leaves protects MC3T3-E1 cells against hydrogen peroxide-induced inhibition of osteoblastic differentiation. J Appl Toxicol. 2010 Oct;30(7):666-73. doi: 10.1002/jat.1539. PMID: 20981859. 11: Wang CR, Ji HW, He SY, Liu RP, Wang XQ, Wang J, Huang CM, Xu YN, Li YH, Kim NH. Chrysoeriol Improves In Vitro Porcine Embryo Development by Reducing Oxidative Stress and Autophagy. Vet Sci. 2023 Feb 10;10(2):143. doi: 10.3390/vetsci10020143. PMID: 36851447; PMCID: PMC9958645. 12: Wongkularb S, Limboonreung T, Tuchinda P, Chongthammakun S. Suppression of PI3K/Akt/mTOR pathway in chrysoeriol-induced apoptosis of rat C6 glioma cells. In Vitro Cell Dev Biol Anim. 2022 Jan;58(1):29-36. doi: 10.1007/s11626-021-00634-x. Epub 2021 Dec 14. PMID: 34907494. 13: Zhang Y, Li Z, Min Q, Palida A, Zhang Y, Tang R, Chen L, Li H. 8-Chrysoeriol, as a potential BCL-2 inhibitor triggers apoptosis of SW1990 pancreatic cancer cells. Bioorg Chem. 2018 Apr;77:478-484. doi: 10.1016/j.bioorg.2018.01.042. Epub 2018 Feb 2. PMID: 29454280. 14: Choi DY, Lee JY, Kim MR, Woo ER, Kim YG, Kang KW. Chrysoeriol potently inhibits the induction of nitric oxide synthase by blocking AP-1 activation. J Biomed Sci. 2005 Dec;12(6):949-59. doi: 10.1007/s11373-005-9028-8. Epub 2005 Oct 14. PMID: 16228289. 15: Liu YX, Chen YJ, Xu BW, Fu XQ, Ding WJ, Li SA, Wang XQ, Wu JY, Wu Y, Dou X, Liu B, Yu ZL. Inhibition of STAT3 signaling contributes to the anti-melanoma effects of chrysoeriol. Phytomedicine. 2023 Jan;109:154572. doi: 10.1016/j.phymed.2022.154572. Epub 2022 Nov 20. PMID: 36610164. 16: Liu Y, Han C, Lu T, Liu Y, Chen H, Yang C, Tu Y, Li Y. Investigation of the interaction between Chrysoeriol and xanthine oxidase using computational and in vitro approaches. Int J Biol Macromol. 2021 Nov 1;190:463-473. doi: 10.1016/j.ijbiomac.2021.08.231. Epub 2021 Sep 8. PMID: 34506859. 17: Gupta A, Behl T, Singh S, Garg M, Tamboli ET, Chigurupati S, Felemban SG, Albarrati A, Albratty M, Meraya AM. Quantification of Luteolin, Apigenin and Chrysoeriol in Tecoma stans by RP-HPLC Method. J Chromatogr Sci. 2023 Mar 23:bmad022. doi: 10.1093/chromsci/bmad022. Epub ahead of print. PMID: 36951424. 18: Zeng X, Shi J, Zhao M, Chen Q, Wang L, Jiang H, Luo F, Zhu L, Lu L, Wang X, Liu Z. Regioselective Glucuronidation of Diosmetin and Chrysoeriol by the Interplay of Glucuronidation and Transport in UGT1A9-Overexpressing HeLa Cells. PLoS One. 2016 Nov 10;11(11):e0166239. doi: 10.1371/journal.pone.0166239. PMID: 27832172; PMCID: PMC5104480. 19: Kim JH, Jin CH. Inhibitory Activity of Flavonoids, Chrysoeriol and Luteolin-7-O-Glucopyranoside, on Soluble Epoxide Hydrolase from Capsicum chinense. Biomolecules. 2020 Jan 24;10(2):180. doi: 10.3390/biom10020180. PMID: 31991570; PMCID: PMC7072517. 20: Tai BH, Cuong NM, Huong TT, Choi EM, Kim JA, Kim YH. Chrysoeriol isolated from the leaves of Eurya ciliata stimulates proliferation and differentiation of osteoblastic MC3T3-E1 cells. J Asian Nat Prod Res. 2009 Sep;11(9):817-23. doi: 10.1080/10286020903117317. PMID: 20183330.