Tetrahydroamentoflavanone (Amentoflavanone) is a potent xanthine oxidase (XO) inhibitor. Tetrahydroamentoflavone exhibits inhibitory effect against XO, with IC50 and Kis of 92 nM and 0.982 μM respectively. Tetrahydroamentoflavone may be utilized in the research of inflammatory diseases and gout.

Physicochemical Properties

Molecular Formula	C30H22O10
Molecular Weight	542.49
Exact Mass	542.121
CAS #	48236-96-0
PubChem CID	326004
Appearance	Typically exists as solid at room temperature
Density	1.6±0.1 g/cm3
Boiling Point	932.8±65.0 °C at 760 mmHg
Flash Point	314.3±27.8 °C
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.745
Source	Cycas beddomei, Cycas revoluta
LogP	5.03
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	3
Heavy Atom Count	40
Complexity	936
Defined Atom Stereocenter Count	0
SMILES	Oc1ccc(cc1)C1CC(=O)c2c(O)cc(O)c(c2O1)-c1cc(ccc1O)C1CC(=O)c2c(O)cc(O)cc2O1
InChi Key	ULTQJSQDLWNWTR-UHFFFAOYSA-N
InChi Code	InChI=1S/C30H22O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-10,24-25,31-36H,11-12H2
Chemical Name	8-[5-(5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms	Tetrahydroamentoflavone; 48236-96-0; Amentoflavanone; CHEMBL4100064; 8-[5-(5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one; NSC295676; IVYFLAVANONE; 3',8'-Binaringenin;
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
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

Targets	Natural biflavonoid; antioxidative; anti-inflammatory; anti-viral; anti-tumor; IC50: 92 nM (XO)[1]. Ki: 0.982 μM (XO)[1].
ln Vitro	Tetrahydroamentoflavone exhibits a 92 nM IC50 and 0.982 μM Ki value, respectively, indicating its inhibitory action against XO [1]. IC₅₀ values of tetrahydroamentoflavone (THA) and allopurinol for XO inhibition were 92 and 100 nM respectively and their corresponding values for K(i) were 0.982 and 0.612 μM respectively. Conclusion: THA was a potent XO inhibitor which could be considered as a drug candidate or chemopreventive agent, after establishing its pharmacological and clinical evaluation. The study results appear to support the claim of the traditional medicine with respect to the efficacy of S. anacardium seed against inflammation and gout[1].
Cell Assay	Activity guided fractionation of S. anacardium seed was conducted using liquid-liquid partition and preparative HPLC. The fractions were evaluated for their XO inhibition and antioxidant activity. The ethyl acetate fraction with the highest XO activity yielded a biflavonoid compound tetrahydroamentoflavone (THA). Lineweaver-Burk (LB) plot for the XO inhibition of THA and allopurinol was constructed from the kinetic data[1].
References	[1]. Tetrahydroamentoflavone (THA) from Semecarpus anacardium as a potent inhibitor of xanthine oxidase. J Ethnopharmacol. 2011 Feb 16;133(3):1117-20.
Additional Infomation	Tetrahydroamentoflavone has been reported in Cycas beddomei, Cycas revoluta, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8434 mL	9.2168 mL	18.4335 mL
	5 mM	0.3687 mL	1.8434 mL	3.6867 mL
	10 mM	0.1843 mL	0.9217 mL	1.8434 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.