Methyl brevifolincarboxylate (Brevifolincarboxylic acid methyl ester) is a potent inhibitor of influenza virus PB2 cap binding. Methyl brevifolincarboxylate has anti-oxidant effect. Methyl brevifolincarboxylate also inhibits platelet aggregation, lipid metabolism, and inflammation.

Physicochemical Properties

Molecular Formula	C14H10O8
Molecular Weight	306.22
Exact Mass	306.038
CAS #	154702-76-8
PubChem CID	5319518
Appearance	Typically exists as solid at room temperature
Density	1.78g/cm3
Boiling Point	633.9ºC at 760mmHg
Flash Point	245.9ºC
Vapour Pressure	1.15E-16mmHg at 25°C
Index of Refraction	1.717
LogP	0.752
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Heavy Atom Count	22
Complexity	579
Defined Atom Stereocenter Count	0
SMILES	O1C(C2=C([H])C(=C(C(=C2C2=C1C(C([H])([H])C2([H])C(=O)OC([H])([H])[H])=O)O[H])O[H])O[H])=O
InChi Key	JNWDNAASYHRXMG-UHFFFAOYSA-N
InChi Code	InChI=1S/C14H10O8/c1-21-13(19)5-3-7(16)12-9(5)8-4(14(20)22-12)2-6(15)10(17)11(8)18/h2,5,15,17-18H,3H2,1H3
Chemical Name	methyl 7,8,9-trihydroxy-3,5-dioxo-1,2-dihydrocyclopenta[c]isochromene-1-carboxylate
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

ln Vitro	At an IC50 value of 8.9 μM, methyl brevifolincarboxylate exhibits strong DPPH free radical scavenging power[2]. The generation of NO and TNF-α in LPS-stimulated macrophages is inhibited by methyl brevifolincarboxylate (10 and 30 μM) [2]. Methyl brevifolincarboxylate (1 and 10 μM) prevents the rat aorta from contracting when norepinephrine (HY-13715) is applied [3]. Inhibiting platelet aggregation by 73.5% is methyl brevifolincarboxylate (5 μM)[4]. The H1N1 and H3N2 influenza viruses, with IC50s of 27.16 μM and 33.41 μM, respectively, are inhibited by methyl brevifolincarboxylate [5]. In primary mouse hepatocytes and OA-treated SK-HEP-1 cells, methyl brevifolincarboxylate (10-80 μM, 48 hours) lowers TG levels [6].
Cell Assay	Cell Viability Assay[6] Cell Types: SK-HEP-1 cells Tested Concentrations: 10, 20, 40, 80 μM Incubation Duration: 48 h Experimental Results: decreased the protein levels of FASN, SREBP-1c and ACC1. Increased the expression of PPAR-α.
References	[1]. Chromatographic fingerprint and the simultaneous determination of five bioactive components of geranium carolinianum L. water extract by high performance liquid chromatography. Int J Mol Sci. 2011;12(12):8740-8749. [2]. Anti-oxidant and inflammatory mediator's growth inhibitory effects of compounds isolated from Phyllanthus urinaria. J Ethnopharmacol. 2008;116(2):333-340. [3]. Vasorelaxant effects of methyl brevifolincarboxylate from the leaves of Phyllanthus niruri. Biol Pharm Bull. 2006 Jan;29(1):177-9. [4]. Inhibitory effects of methyl brevifolincarboxylate isolated from Phyllanthus niruri L. on platelet aggregation. Biol Pharm Bull. 2007 Feb;30(2):382-4.
Additional Infomation	Methyl brevifolincarboxylate is an organic heterotricyclic compound that is 1,2,3,5-tetrahydrocyclopenta[c]isochromene substituted by hydroxy groups at positions 7, 8 and 9, oxo groups at positions 3 and 5 and a methoxycarbonyl group at position 1. Isolated from Phyllanthus urinaria and Phyllanthus niruri, it exhibits vasorelaxant activity. It has a role as a metabolite, a vasodilator agent, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, a radical scavenger and a platelet aggregation inhibitor. It is an organic heterotricyclic compound, a delta-lactone, a member of phenols and a cyclic ketone. Methyl brevifolincarboxylate has been reported in Euphorbia maculata and Phyllanthus niruri 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	3.2656 mL	16.3281 mL	32.6563 mL
	5 mM	0.6531 mL	3.2656 mL	6.5313 mL
	10 mM	0.3266 mL	1.6328 mL	3.2656 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.