8-prenylnaringenin is a prenyl flavonoid extracted from the hop spike Humulus lupulus and has cell toxicity/cytotoxicity. 8-prenylnaringenin can produce anti-proliferation activity on HCT-116 colon cancer/tumor cells by inducing apoptosis mediated by endogenous and extrinsic pathways. 8-Prenylnaringenin can promote recovery from rest-induced disuse muscle atrophy in mice by activating the Akt phosphorylation pathway.

Physicochemical Properties

Molecular Formula	C20H20O5
Molecular Weight	340.38
Exact Mass	340.131
CAS #	53846-50-7
PubChem CID	480764
Appearance	White to off-white solid powder
Density	1.3±0.1 g/cm3
Boiling Point	597.6±50.0 °C at 760 mmHg
Flash Point	216.4±23.6 °C
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.642
LogP	5.28
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	25
Complexity	504
Defined Atom Stereocenter Count	1
SMILES	CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C
InChi Key	LPEPZZAVFJPLNZ-SFHVURJKSA-N
InChi Code	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
Chemical Name	(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms	Sophoraflavanone B YS04 Flavaprenin 8-Prenylnaringenin 8 Prenylnaringenin 8Prenylnaringenin
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1].Antiproliferative and apoptotic activities of 8-prenylnaringenin against human colon cancer cells. Life Sci. 2019 Jul 3:116633. [2].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].In Vitro Effect of 8-Prenylnaringenin and Naringenin on Fibroblasts and Glioblastoma Cells-Cellular Accumulation and Cytotoxicity. Molecules. 2017 Jun 30;22(7).

Additional Infomation

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 trihydroxyflavanone, a member of 4'-hydroxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin. It is a conjugate acid of a sophoraflavanone B(1-). 8-Prenylnaringenin has been reported in Humulus lupulus, Maclura pomifera, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~250 mg/mL (~734.49 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.9379 mL	14.6895 mL	29.3789 mL
	5 mM	0.5876 mL	2.9379 mL	5.8758 mL
	10 mM	0.2938 mL	1.4689 mL	2.9379 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.