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Atraric acid (Methyl atrarate)

Cat No.:V67600 Purity: ≥98%
Atraric acid (Methyl atrarate) is a specific androgen receptor antagonist (inhibitor) with anti-inflammatory and anti-cancer effects.
Atraric acid (Methyl atrarate)
Atraric acid (Methyl atrarate) Chemical Structure CAS No.: 4707-47-5
Product category: p38 MAPK
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
Other Sizes
Official Supplier of:
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Product Description
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.
Biological Activity I Assay Protocols (From Reference)
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.
These protocols are for reference only. InvivoChem does not independently validate these methods.
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)
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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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