Atraric acid

Names

[ Name ]:
Atraric acid

[Synonym ]:
QR CQ B1 E1 DVO1
EINECS 225-193-0
METHYL 2,4-DIHYDROXY-3,6-DIMETHYLBENZOATE
Methyl atratate
MFCD00157202
Benzoic acid, 2,4-dihydroxy-3,6-dimethyl-, methyl ester
2,4-Dihydroxy-3,6-dimethylbenzoic acid methyl ester

Biological Activity

[Description]:

Atraric acid (Methyl atrarate) is a specific androgen receptor (AR) antagonist with anti-inflammatory and anticancer effects. Atraric acid represses the expression of the endogenous prostate specific antigen gene in both LNCaP and C4-2 cells. Atraric acid can also inhibit the synthesis of NO and cytokine, and suppress the MAPK-NFκB signaling pathway. Atraric acid can be used to research prostate diseases and inflammatory diseases[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Others >> Androgen Receptor

[Target]

Androgen receptor, NO synthesis, MAPK-NFκB pathway[1][2]

[In Vitro]

Atraric acid (10 μM; CV1 cells) represses the transactivation function mediated by Dihydrotestosterone-induced human AR[1]. Atraric acid (10 μM; PCa cells) inhibits the expression of the PSA gene in both androgen-dependent and androgen-independent PCa cells[1]. Atraric acid (1-300 μM; 24 h) dose-dependently inhibits pro-inflammatory cytokine, nitric oxide, prostaglandin E2 in LPS-stimulated RAW264.7 cells, but does not influence the cell viability[2]. Atraric acid (100 and 300 μM; 18 h or 4 h) downregulates the expression of phosphorylated IκB, extracellular signal-regulated kinases (ERK) and nuclear factor kappa B (NFκB) signaling pathway to exhibit anti-inflammatory effects in LPS-stimulated RAW264.7 cells[2]. Cell Viability Assay[2] Cell Line: RAW264.7 cells Concentration: 1-300 μM Incubation Time: 24 h Result: Did not influence the cell viability. Western Blot Analysis[2] Cell Line: RAW264.7 cells Concentration: 100 and 300 μM Incubation Time: 18 h or 4 h Result: Inhibited LPS-Induced expression of iNOS and COX-2 in a dose-dependent manner. Suppressed LPS-stimulated phosphorylation of the Nfκb signaling pathway.

[In Vivo]

Atraric acid (10, 30 mg/kg; i.p.; single dosage) inhibits the production of pro-inflammatory cytokines and reduces pathological damages in LPS-induced endotoxin shock mice[2]. Animal Model: Female BALB/c mice (7 weeks old, 17-20 g; LPS-induced endotoxin shock)[2] Dosage: 10, 30 mg/kg Administration: i.p.; single dosage Result: Inhibited the production of pro-inflammatory cytokines. Reduced pathological damages such as vasodilation and bleeding.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
360.7±22.0 °C at 760 mmHg

[ Melting Point ]:
141-146 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₂O₄

[ Molecular Weight ]:
196.200

[ Flash Point ]:
143.9±15.8 °C

[ Exact Mass ]:
196.073563

[ PSA ]:
66.76000

[ LogP ]:
2.84

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.570

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ HS Code ]:
2918199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918199090

[ Summary ]:
2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%