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Chemical Structure| 69-72-7 Chemical Structure| 69-72-7

Structure of Salicylic acid
CAS No.: 69-72-7

Chemical Structure| 69-72-7

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Salicylic acid, a natural product extract from Willow bark, well known as an antiinflammatory inhibitor of cyclooxygenase activity.

Synonyms: 2-Hydroxybenzoic acid; NSC 180

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Product Citations

Product Citations

Hegde, Pooja ; Orimoloye, Moyosore O. ; Sharma, Sachin ; Engelhart, Curtis A. ; Schnappinger, Dirk ; Aldrich, Courtney C.

Abstract: Tuberculosis (TB), caused by Mycobacterium tuberculosis (Mtb) is a leading cause of infectious disease mortality. The salicylic acid derived small mol. siderophores known as mycobactins are essential in vivo for iron acquisition of Mtb where iron is restricted in the host. Herein, we synthesize and explore the mechanism of action of polyfluorinated salicylic acid derivates, which were previously reported to possess potent antimycobacterial activity. We hypothesized fluorinated salicylic acid derivates may inhibit mycobactin biosynthesis through initial bioactivation and conversion to downstream metabolites that block late steps in assembly of the mycobactins. Enzymic studies demonstrated that some of the fluorinated salicylic acid derivatives compounds were readily activated by the bifunctional adenylating enzyme MbtA, responsible for incorporation of salicylic acid into the mycobactin biosynthetic pathway; however, they did not inhibit mycobactin biosynthesis as confirmed by LS-MS/MS using an authentic synthetic mycobactin standard Further mechanistic anal. of the most active derivative (Sal-4) using an MbtA-overexpressing Mtb strain as well as complementation studies with iron and salicylic acid revealed Sal-4 cannot be antagonized by overexpression of MbtA or through supplementation with iron or salicylic acid. Taken together, our results indicate the observed antimycobacterial activity of polyfluorinated salicylic acid derivative is independent of mycobactin biosynthesis.

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Product Details of Salicylic acid

CAS No. :69-72-7
Formula : C7H6O3
M.W : 138.12
SMILES Code : OC1=CC=CC=C1C(O)=O
Synonyms :
2-Hydroxybenzoic acid; NSC 180
MDL No. :MFCD00002439
InChI Key :YGSDEFSMJLZEOE-UHFFFAOYSA-N
Pubchem ID :338

Safety of Salicylic acid

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H318-H361
Precautionary Statements:P201-P202-P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P308+P313-P405-P501

Isoform Comparison

Biological Activity

Target
  • COX

In Vitro:

Cell Line
Concentration Treated Time Description References
Arabidopsis pollen tubes 1-50 µM 3 hours SA inhibited pollen tube elongation and germination in a concentration-dependent manner. Mol Plant. 2016 Nov 7;9(11):1478-1491

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Arabidopsis thaliana Arabidopsis seedlings Medium treatment 100 µM 13 or 24 hours Salicylic acid regulates PIN2 auxin transporter hyperclustering and root gravitropic growth via Remorin-dependent lipid nanodomain organisation in Arabidopsis thaliana. New Phytol. 2021 Jan;229(2):963-978
Arabidopsis thaliana Wild-type and transgenic plants Culture medium treatment 20 µM 3 hours SA inhibited pollen tube growth, while MeSA promoted pollen tube growth. Mol Plant. 2016 Nov 7;9(11):1478-1491

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

7.24mL

1.45mL

0.72mL

36.20mL

7.24mL

3.62mL

72.40mL

14.48mL

7.24mL

References

 

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