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Homoeriodictyol

CAT: 0804-HY-N8210-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N8210-01Size:1 mg
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Description
Homoeriodictyol is an orally active, bitter-tasting flavanone that can penetrate the blood-brain barrier. Homoeriodictyol enhances synaptic-related protein expression through NCOA4-mediated ferritin autophagy. Homoeriodictyol improves memory impairment in mice by inhibiting the NLRP3 inflammasome. Homoeriodictyol protects human endothelial cells from oxidative damage by activating Nrf2 and inhibiting mitochondrial dysfunction. Homoeriodictyol enhances ROS activity and induces apoptosis, exhibiting anticancer effects. Homoeriodictyol inhibits the survival and migration of androgen-resistant prostate cancer cells in vitro. Homoeriodictyol exerts antinociceptive activity in mice in vivo[1][2][3][4][5][6].
CAS Number
446-71-9
UNSPSC
12352005
Target
Apoptosis; Autophagy; Caspase; Drug Metabolite; Keap1-Nrf2; MDM-2/p53; MMP; PARP; Reactive Oxygen Species (ROS)
Type
Reference compound
Related Pathways
Apoptosis; Autophagy; Cell Cycle/DNA Damage; Epigenetics; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Cancer; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/homoeriodictyol.html
Purity
99.83
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O=C1C[C@@H](C2=CC=C(O)C(OC)=C2)OC3=CC(O)=CC(O)=C13
Molecular Formula
C16H14O6
Molecular Weight
302.28
References & Citations
[1]Zhang M, et al. Hesperidin alleviated dendritic spines through inhibiting ferritinophagy via HERC2-NCOA4 ubiquitination in CUMS mice. Phytomedicine. 2024 Dec;135:156132.|[2]Guo P, et al. Eriodictyol and Homoeriodictyol Improve Memory Impairment in Aβ25-35-Induced Mice by Inhibiting the NLRP3 Inflammasome. Molecules. 2022 Apr 12;27 (8) :2488.|[3]Shen T, et al. Homoeriodictyol protects human endothelial cells against oxidative insults through activation of Nrf2 and inhibition of mitochondrial dysfunction. Vascul Pharmacol. 2018 Oct;109:72-82.|[4]Quaiser Saquib, et al. Anticancer efficacies of persicogenin and homoeriodictyol isolated from Rhus retinorrhoea. Process Biochemistry, ISSN: 1359-5113, Vol: 95, Page: 186-196.|[5]Al-Bzour M H, et al. Exploring the antinociceptive potential of homoeriodictyol in nociception models[J]. J. Pharm. Pharmacogn. Res, 2024, 12: 615-623.|[6]Güvenç A, et al. HOMOERIODICTYOL INHIBITS SURVIVAL AND MIGRATION OF ANDROGEN-RESISTANT PROSTATE CANCER CELLS IN VITRO. Exp Oncol. 2025 Jul 11;47 (1) :34-43.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
Caspase 3; Caspase 9

Chemical Information

Homoeriodictyol

Homoeriodictyol is a trihydroxyflavanone that consists of 3'-methoxyflavanone in which the three hydroxy substituents are located at positions 4', 5, and 7. It has a role as a metabolite and a flavouring agent. It is a member of 4'-hydroxyflavanones, a member of 3'-methoxyflavanones, a monomethoxyflavanone and a trihydroxyflavanone. It is functionally related to an eriodictyol.

CAS Number446-71-9
PubChem CID73635
IUPAC Name(2S)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Molecular FormulaC16H14O6
Molecular Weight302.28
XLogP2.4
Topological Polar Surface Area96.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Heavy Atom Count22
Formal Charge0
Complexity413
SMILES
COC1=C(C=CC(=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O)O
InChI
InChI=1S/C16H14O6/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/h2-6,13,17-19H,7H2,1H3/t13-/m0/s1
InChIKey
FTODBIPDTXRIGS-ZDUSSCGKSA-N
Chemical Structure
2D Structure
2D structure of Homoeriodictyol
CAS: 446-71-9
CID: 73635
Formula: C16H14O6
MW: 302.28
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight302.28
XLogP32.4
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass302.07903816
Monoisotopic Mass302.07903816
Topological Polar Surface Area96.2 Ų
Heavy Atom Count22
Formal Charge0
Complexity413
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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