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Chemical Structure| 490-79-9 Chemical Structure| 490-79-9

Structure of 2,5-Dihydroxybenzoic Acid
CAS No.: 490-79-9

Chemical Structure| 490-79-9

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Gentisic acid is a natural product isolated and purified from the roots of Gentiana scabra Bunge.

Synonyms: Gentisic Acid; NSC 78825; NSC 49098

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Berrow, Stuart R ; Raistrick, Thomas ; Mandle, Richard J ; Gleeson, Helen F ;

Abstract: The observation of auxetic behaviour (i.e. negative Poisson’s ratio) in liquid crystal elastomers (LCEs) presents an exciting opportunity to explore application areas previously inaccessible to LCEs. Since its initial discovery, research has focused on improving understanding of the underpinning physics that drives the auxetic response, the structure-property relationships that enable the response to be tuned, and LCE properties such as the refractive index. However, the auxetic LCE materials reported to date have made use of either mechanical strain during fabrication, or unreactive ‘templates’ to stabilize the nematic ordering in the precursors. The latter approach provides excellent monodomain films, but there is unavoidable anisotropic shrinkage of the LCE. Both processes previously employed create complications towards manufacturing and scale-up. In this article, we report the first example of an auxetic LCE synthesized through surface alignment without the use of a non-reactive ‘template’ and thus without the need for a washout. The LCE includes both terminally and laterally attached mesogens, presents an auxetic threshold of 76% strain, and displays a comparable dependence of auxetic behaviour on its glass transition temperature as that reported in the literature. This work presents an exciting milestone in the journey towards realizing applications for auxetic LCEs.

Keywords: Liquid crystal elastomer ; Auxetic ; Mechanical metamaterials ; Elastomer ; Network

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Hassan, Sara A ; Zaater, Marwa A ; Abdel-Rahman, Islam M ; Ibrahim, Elsayed A ; El Kerdawy, Ahmed M ; Abouelmagd, Sara A

Abstract: The development of new forms of existing APIs with enhanced physicochemical properties is critical for improving their therapeutic potential. In this context, ionic liquids (ILs) and deep eutectic solvents (DESs) have gained significant attention in recent years due to their unique properties and potential for solubility enhancement. In this study, we explore the role of different counterparts in the formation of IL/DESs with piperine (PI), a poorly water-soluble drug. After screening a library of fourteen counterpart molecules, ten liquid PI-counterpart systems were developed and investigated. Thermal analysis confirmed the formation of IL/DES, while computational and spectroscopic studies revealed that hydrogen bonding played a crucial role in the interaction between PI and the counterparts, confirming DES formation. The solubility enhancement of PI in these systems ranged from ∼ 36 % to 294 %, with PI-Oxalic acid (OA) exhibiting the highest saturation solubility (49.71 μg/mL) and PI-Ibuprofen (IB) the lowest (17.23 μg/mL). The presence of hydrogen bonding groups in counterparts was key to successful DES formation. A negative correlation was observed between solubility and logP (r =  − 0.75, p* = 0.0129), while a positive correlation was found between solubility and normalized polar surface area (PSA) (r = 0.68, p* = 0.029). PI-OA and PI-IB were located at the extreme ends of these regression lines, further validating the relationship between these properties and solubility enhancement. These findings highlight essential aspects of rational IL/DES design, optimizing their properties for broader applications.

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Alternative Products

Product Details of 2,5-Dihydroxybenzoic Acid

CAS No. :490-79-9
Formula : C7H6O4
M.W : 154.12
SMILES Code : OC(=O)C1=C(O)C=CC(O)=C1
Synonyms :
Gentisic Acid; NSC 78825; NSC 49098
MDL No. :MFCD00002460
InChI Key :WXTMDXOMEHJXQO-UHFFFAOYSA-N
Pubchem ID :3469

Safety of 2,5-Dihydroxybenzoic Acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of 2,5-Dihydroxybenzoic Acid

RTK

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
HepG2 cells 0.001, 0.01, 0.1, 1, 10 μM 24 h To evaluate the effect of 2,5-DHBA on oleic acid-induced lipid accumulation in HepG2 cells. Results showed that 2,5-DHBA significantly reduced lipid accumulation in a dose-dependent manner without affecting cell viability. Nutrients. 2025 May 28;17(11):1835

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice Bdh2 null mice Intraperitoneal injection 500 mg/kg Two doses, 24 hours apart, sacrificed 24 hours after last injection Supplementation with 2,5-DHBA alleviates splenic iron overload in bdh2 null mice Mol Cell Biol. 2014 Jul;34(13):2533-46
FVB mice High-fat diet-induced MASLD mouse model Oral gavage 1, 10, 100 mg/kg Once daily for 7 days (short-term experiment) or 4 weeks (long-term experiment) To evaluate the effect of 2,5-DHBA on hepatic lipid accumulation in HFD-induced MASLD mice. Results showed that 2,5-DHBA significantly reduced hepatic lipid accumulation in a dose-dependent manner and improved liver histology. Nutrients. 2025 May 28;17(11):1835

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

6.49mL

1.30mL

0.65mL

32.44mL

6.49mL

3.24mL

64.88mL

12.98mL

6.49mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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