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8-​Prenylnaringenin

CAT: 0804-HY-N2787-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2787-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
8-Prenylnaringenin is an orally active prenyl flavonoid. 8-Prenylnaringenin can be isolated from the hop spike Humulus lupulus. 8-Prenylnaringenin activates the PI3K/Akt pathway and the AMPK pathway, upregulates OXPHOS complexes (II, III, and V) and Sirt1, and reduces ROS production and SOD activity. 8-Prenylnaringenin improves muscle atrophy and obesity and inhibits angiogenesis. 8-Prenylnaringenin exhibits anticancer activity against glioblastoma and colon cancer. 8-Prenylnaringenin also has LH/FSH regulatory activity. 8-prenylnaringenin may be used in bone health research[1][2][3][4][5][6][7][8].
CAS Number
53846-50-7
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Akt; AMPK; PI3K; Reactive Oxygen Species (ROS) ; Sirtuin; SOD
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; Epigenetics; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB; PI3K/Akt/mTOR
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Endocrinology; Metabolic Disease; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/8-prenylnaringenin.html
Purity
99.63
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=C(C/C=C(C)\C)C(O)=CC(O)=C13
Molecular Formula
C20H20O5
Molecular Weight
340.37
Precautions
H302, H315, H319, H335
References & Citations
[1]Koosha S, et al. Antiproliferative and apoptotic activities of 8-prenylnaringenin against human colon cancer cells. Life Sci. 2019 Jul 3:116633.|[2]Mukai R, et al. 8-Prenylnaringenin promotes recovery from immobilization-induced disuse muscle atrophy through activation of the Akt phosphorylation pathway in mice. Am J Physiol Regul Integr Comp Physiol. 2016 Dec 1;311 (6) :R1022-R1031.|[3]Stompor M, et al. In Vitro Effect of 8-Prenylnaringenin and Naringenin on Fibroblasts and Glioblastoma Cells-Cellular Accumulation and Cytotoxicity. Molecules. 2017 Jun 30;22 (7) .|[4]Blanquer-Rosselló MM, et al. Effect of xanthohumol and 8-prenylnaringenin on MCF-7 breast cancer cells oxidative stress and mitochondrial complexes expression. J Cell Biochem. 2013 Dec;114 (12) :2785-94. |[5]Pepper MS, et al. 8-prenylnaringenin, a novel phytoestrogen, inhibits angiogenesis in vitro and in vivo. J Cell Physiol. 2004 Apr;199 (1) :98-107.|[6]Okada F, et al. 8-Prenylnaringenin suppresses obesity in high-fat diet-fed C57BL/6J mice via adiponectin secretion. J Clin Biochem Nutr. 2025 Jul;77 (1) :64-73.|[7]Christoffel J, et al. Effects of 8-prenylnaringenin on the hypothalamo-pituitary-uterine axis in rats after 3-month treatment. J Endocrinol. 2006 Mar;188 (3) :397-405. |[8]Hoffmann DB, et al. Effects of 8-Prenylnaringenin and Whole-Body Vibration Therapy on a Rat Model of Osteopenia. J Nutr Metab. 2016;2016:6893137.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
SIRT1

Chemical Information

Sophoraflavanone B

Sophoraflavanone B is a trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8. It has a role as a platelet aggregation inhibitor and a plant metabolite. It is a member of 4'-hydroxyflavanones, a (2S)-flavan-4-one and a trihydroxyflavanone. It is functionally related to a (S)-naringenin. It is a conjugate acid of a sophoraflavanone B(1-).

CAS Number53846-50-7
PubChem CID480764
IUPAC Name(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Molecular FormulaC20H20O5
Molecular Weight340.4
XLogP4.3
Topological Polar Surface Area87
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count25
Formal Charge0
Complexity504
SMILES
CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C
InChI
InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1
InChIKey
LPEPZZAVFJPLNZ-SFHVURJKSA-N
Chemical Structure
2D Structure
2D structure of Sophoraflavanone B
CAS: 53846-50-7
CID: 480764
Formula: C20H20O5
MW: 340.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight340.4
XLogP34.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass340.13107373
Monoisotopic Mass340.13107373
Topological Polar Surface Area87 Ų
Heavy Atom Count25
Formal Charge0
Complexity504
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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