(±)-Eriodictyol | CAS#4049-38-1 | TRPV1 antagonist

MedKoo Cat#: 463294 | Name: (±)-Eriodictyol

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Description:

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

(±)-Eriodictyol is a potent TRPV1 antagonist. It inhibits capsaicin-induced Ca2+ influx in synaptosomes and exhibits antinociceptive activity in animal models without affecting body temperature. (±)-Eriodictyol is also an antioxidant that protects against H2O2-induced neurotoxicity in vitro by activation of Nrf2/ARE signaling. Modeling studies predict binding to ACE2 preventing its interaction with SARS-CoV-2 S protein. It is also a naturally-derived flavonoid that is orally bioavailable.

Chemical Structure

(±)-Eriodictyol

CAS#4049-38-1

Theoretical Analysis

MedKoo Cat#: 463294

Name: (±)-Eriodictyol

CAS#: 4049-38-1

Chemical Formula: C15H12O6

Exact Mass: 288.0634

Molecular Weight: 288.26

Elemental Analysis: C, 62.50; H, 4.20; O, 33.30

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks

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Related CAS #

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Synonym

(±)-Eriodictyol;

IUPAC/Chemical Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-4-one

InChi Key

SBHXYTNGIZCORC-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2

SMILES Code

OC1=CC(O)=C2C(CC(OC2=C1)C3=CC(O)=C(O)C=C3)=O

Appearance

Solid powder

Purity

>95% (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 288.26 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: Li L, Li WJ, Zheng XR, Liu QL, Du Q, Lai YJ, Liu SQ. Eriodictyol ameliorates cognitive dysfunction in APP/PS1 mice by inhibiting ferroptosis via vitamin D receptor-mediated Nrf2 activation. Mol Med. 2022 Jan 29;28(1):11. doi: 10.1186/s10020-022-00442-3. PMID: 35093024; PMCID: PMC8800262. 2: Hu Q, Qu C, Xiao X, Zhang W, Jiang Y, Wu Z, Song D, Peng X, Ma X, Zhao Y. Flavonoids on diabetic nephropathy: advances and therapeutic opportunities. Chin Med. 2021 Aug 7;16(1):74. doi: 10.1186/s13020-021-00485-4. PMID: 34364389; PMCID: PMC8349014. 3: Barreca D, Gattuso G, Bellocco E, Calderaro A, Trombetta D, Smeriglio A, Laganà G, Daglia M, Meneghini S, Nabavi SM. Flavanones: Citrus phytochemical with health-promoting properties. Biofactors. 2017 Jul 8;43(4):495-506. doi: 10.1002/biof.1363. Epub 2017 May 12. PMID: 28497905. 4: Islam A, Islam MS, Rahman MK, Uddin MN, Akanda MR. The pharmacological and biological roles of eriodictyol. Arch Pharm Res. 2020 Jun;43(6):582-592. doi: 10.1007/s12272-020-01243-0. Epub 2020 Jun 27. PMID: 32594426. 5: Fernández J, Silván B, Entrialgo-Cadierno R, Villar CJ, Capasso R, Uranga JA, Lombó F, Abalo R. Antiproliferative and palliative activity of flavonoids in colorectal cancer. Biomed Pharmacother. 2021 Nov;143:112241. doi: 10.1016/j.biopha.2021.112241. Epub 2021 Sep 30. PMID: 34649363. 6: Li C, Wang C. Retraction of "Eriodictyol corrects functional recovery and myelin loss in SCI rats". Transl Neurosci. 2023 Feb 14;14(1):20220275. doi: 10.1515/tnsci-2022-0275. PMID: 36824349; PMCID: PMC9942166. 7: Deng Z, Hassan S, Rafiq M, Li H, He Y, Cai Y, Kang X, Liu Z, Yan T. Pharmacological Activity of Eriodictyol: The Major Natural Polyphenolic Flavanone. Evid Based Complement Alternat Med. 2020 Dec 12;2020:6681352. doi: 10.1155/2020/6681352. PMID: 33414838; PMCID: PMC7752289. 8: Lee J, Sim W, Han SI, Byeon JH, Jin SB, Binti Morshidi NAA, Hong YY, Jung Y, Kim JH. Eriodictyol Attenuates Cholangiocarcinoma Malignancy by Regulating HMOX1 Expression: An In Vitro Study. Anticancer Res. 2022 Aug;42(8):3789-3798. doi: 10.21873/anticanres.15869. PMID: 35896263. 9: Shan H, Zhang X, Mi Y, Jia J, Wang B, Yang Q. Eriodictyol Suppresses Gastric Cancer Cells via Inhibition of PI3K/AKT Pathway. Pharmaceuticals (Basel). 2022 Nov 27;15(12):1477. doi: 10.3390/ph15121477. PMID: 36558929; PMCID: PMC9788236. 10: Nakashima F, Loh WQ, Wakabayashi M, Shimomura S, Hattori H, Kita M, Inoue A, Uchida K, Shibata T. Eriodictyol and thymonin act as GPR35 agonists. Biosci Biotechnol Biochem. 2023 Sep 4:zbad125. doi: 10.1093/bbb/zbad125. Epub ahead of print. PMID: 37667527. 11: Wen S, Hu M, Xiong Y. Effect of Eriodictyol on Retinoblastoma via the PI3K/Akt Pathway. J Healthc Eng. 2021 Nov 11;2021:6091585. doi: 10.1155/2021/6091585. Retraction in: J Healthc Eng. 2023 Oct 18;2023:9824504. PMID: 34804455; PMCID: PMC8601792. 12: Wu X, Liu J, Liu D, Yuwen M, Koffas MAG, Zha J. Biosynthesis of eriodictyol from tyrosine by Corynebacterium glutamicum. Microb Cell Fact. 2022 May 14;21(1):86. doi: 10.1186/s12934-022-01815-3. PMID: 35568867; PMCID: PMC9107716. 13: Theoharides TC, Kempuraj D. Role of SARS-CoV-2 Spike-Protein-Induced Activation of Microglia and Mast Cells in the Pathogenesis of Neuro-COVID. Cells. 2023 Feb 22;12(5):688. doi: 10.3390/cells12050688. PMID: 36899824; PMCID: PMC10001285. 14: Yao L, Liu W, Bashir M, Nisar MF, Wan CC. Eriocitrin: A review of pharmacological effects. Biomed Pharmacother. 2022 Oct;154:113563. doi: 10.1016/j.biopha.2022.113563. Epub 2022 Aug 18. PMID: 35987162. 15: Zhang M, Tang Z. Therapeutic potential of natural molecules against Alzheimer's disease via SIRT1 modulation. Biomed Pharmacother. 2023 May;161:114474. doi: 10.1016/j.biopha.2023.114474. Epub 2023 Mar 4. PMID: 36878051. 16: Guo S, Xing N, Xiang G, Zhang Y, Wang S. Eriodictyol: a review of its pharmacological activities and molecular mechanisms related to ischemic stroke. Food Funct. 2023 Feb 21;14(4):1851-1868. doi: 10.1039/d2fo03417d. Erratum in: Food Funct. 2023 May 22;14(10):4949. PMID: 36757280. 17: Wang Z, Lan Y, Chen M, Wen C, Hu Y, Liu Z, Ye L. Eriodictyol, Not Its Glucuronide Metabolites, Attenuates Acetaminophen-Induced Hepatotoxicity. Mol Pharm. 2017 Sep 5;14(9):2937-2951. doi: 10.1021/acs.molpharmaceut.7b00345. Epub 2017 Jul 17. PMID: 28654297. 18: Li CZ, Jin HH, Sun HX, Zhang ZZ, Zheng JX, Li SH, Han SH. Eriodictyol attenuates cisplatin-induced kidney injury by inhibiting oxidative stress and inflammation. Eur J Pharmacol. 2016 Feb 5;772:124-30. doi: 10.1016/j.ejphar.2015.12.042. Epub 2015 Dec 23. PMID: 26723515. 19: Manthey JA, Ferreira PS, Cesar TB. Influences of Solubility and Vehicle Carriers on Eriodictyol Pharmacokinetics in Rats. J Agric Food Chem. 2022 Apr 20;70(15):4667-4676. doi: 10.1021/acs.jafc.2c00319. Epub 2022 Apr 8. PMID: 35394285. 20: He J, Fu H, Li C, Deng Z, Chang H. Eriodictyol inhibits breast carcinogenesis by targeting circ_0007503 and repressing PI3K/Akt pathway. Phytomedicine. 2022 Jul 20;102:154159. doi: 10.1016/j.phymed.2022.154159. Epub 2022 May 7. PMID: 35580441.