Atraric acid (Methyl atrarate) is a specific androgen receptor antagonist (inhibitor) with anti-inflammatory and anti-cancer effects. Atraric acid inhibits endogenous prostate-specific antigen gene expression in LNCaP and C4-2 cells. Atraric acid can also inhibit the synthesis of NO and cytokines, and inhibit the MAPK-NFκB signaling pathway. Atraric acid may be utilized in the study of prostate disease and inflammatory diseases.

Physicochemical Properties

Molecular Formula	C10H12O4
Molecular Weight	196.20
Exact Mass	196.073
CAS #	4707-47-5
PubChem CID	78435
Appearance	White to off-white solid powder
Density	1.3±0.1 g/cm3
Boiling Point	360.7±22.0 °C at 760 mmHg
Melting Point	141-146 °C(lit.)
Flash Point	143.9±15.8 °C
Vapour Pressure	0.0±0.8 mmHg at 25°C
Index of Refraction	1.570
LogP	2.84
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Heavy Atom Count	14
Complexity	216
Defined Atom Stereocenter Count	0
InChi Key	UUQHKWMIDYRWHH-UHFFFAOYSA-N
InChi Code	InChI=1S/C10H12O4/c1-5-4-7(11)6(2)9(12)8(5)10(13)14-3/h4,11-12H,1-3H3
Chemical Name	methyl 2,4-dihydroxy-3,6-dimethylbenzoate
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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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	Androgen receptor, NO synthesis, MAPK-NFκB pathway[1][2]
ln Vitro	The transactivation function mediated by dihydrotestosterone-induced human AR is repressed by atrazine (10 μM; CV1 cells)[1]. The expression of the PSA gene is inhibited in both androgen-dependent and androgen-independent PCa cells by atraric acid (10 μM)[1]. In LPS-stimulated RAW264.7 cells, traric acid (1-300 μM; 24 h) dose-dependently inhibits prostaglandin E2, nitric oxide, and pro-inflammatory cytokines, but has no effect on cell viability[2]. In LPS-stimulated RAW264.7 cells, astraricic acid (100 and 300 μM; 18 h or 4 h) exhibits anti-inflammatory effects by downregulating the expression of phosphorylated IκB, extracellular signal-regulated kinases (ERK), and nuclear factor kappa B (NFκB) signaling pathway[2].
ln Vivo	In LPS-induced endotoxin shock mice, traric acid (10, 30 mg/kg; ip; single dosage) decreases pathological damages and suppresses the production of pro-inflammatory cytokines[2].
Cell Assay	Cell Viability Assay[2] Cell Types: RAW264.7 cells Tested Concentrations: 1-300 μM Incubation Duration: 24 h Experimental Results: Did not influence the cell viability. Western Blot Analysis[2] Cell Types: RAW264 .7 cells Tested Concentrations: 100 and 300 μM Incubation Duration: 18 h or 4 h Experimental Results: Inhibited LPS-Induced expression of iNOS and COX-2 in a dose-dependent manner. Suppressed LPS-stimulated phosphorylation of the Nfκb signaling pathway.
Animal Protocol	Animal/Disease Models: Female balb/c (Bagg ALBino) mouse (7 weeks old , 17-20 g; LPS-induced endotoxin shock)[2] Doses: 10, 30 mg/kg Route of Administration: ip; single dosage Experimental Results: Inhibited the production of pro-inflammatory cytokines. decreased pathological damages such as vasodilation and bleeding.
References	[1]. The natural compound atraric acid is an antagonist of the human androgen receptor inhibiting cellular invasiveness and prostate cancer cell growth. J Cell Mol Med. 2009 Aug;13(8B):2210-2223. [2]. Roell D, Baniahmad A. The natural compounds atraric acid and N-butylbenzene-sulfonamide as antagonists of the human androgen receptor and inhibitors of prostate cancer cell growth. Mol Cell Endocrinol. 2011 Jan 30;332(1-2):1-8.
Additional Infomation	Methyl beta-orcinolcarboxylate is a 4-hydroxybenzoate ester. Methyl 2,4-dihydroxy-3,6-dimethylbenzoate has been reported in Usnea undulata, Stereocaulon alpinum, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (509.68 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (12.74 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 25.0 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	5.0968 mL	25.4842 mL	50.9684 mL
	5 mM	1.0194 mL	5.0968 mL	10.1937 mL
	10 mM	0.5097 mL	2.5484 mL	5.0968 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.