Gentisic acid | CAS#490-79-9 | oxidative product

Gentisic acid
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 592307

CAS#: 490-79-9

Description: Gentisic acid is an oxidative product of saligenin.

Chemical Structure

Gentisic acid

CAS# 490-79-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 592307
Name: Gentisic acid
CAS#: 490-79-9
Chemical Formula: C7H6O4
Exact Mass: 154.03
Molecular Weight: 154.120
Elemental Analysis: C, 54.55; H, 3.92; O, 41.52

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 230
250mg	USD 500
1g	USD 1070
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Gentisic acid; NSC 27224; NSC-27224; NSC27224

IUPAC/Chemical Name: Benzoic acid, 2,5-dihydroxy-

InChi Key: WXTMDXOMEHJXQO-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)

SMILES Code: O=C(O)C1=CC(O)=CC=C1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	2,5-Dihydroxybenzoic acid is a derivative of benzoic and a powerful inhibitor of fibroblast growth factors.
In vitro activity:	The WST-1 assay was performed to measure cell viability after GA (gentisic acid) treatment (200, 400, 600, and 800 μM) of 3T3-L1 cells for 24 h. GA treatment did not show considerable cytotoxic effects until a concentration of 800 μM on 3T3-L1 cells (Fig. 2A). As shown in Figs. 2B and 2C, GA treatment successfully inhibited lipid accumulation in a dose-dependent manner in comparison to that in fully differentiated 3T3-L1 cells. The mRNA and protein expression of major adipogenic transcription factors, C/EBPα and PPARγ, were measured using RT-PCR and western blotting analysis. Results showed that GA treatment reduced the mRNA and protein expression of crucial adipogenesis-related transcription factors (Fig. 2D). Reference: J Microbiol Biotechnol. 2021 Aug 28;31(8):1079-1087. https://pubmed.ncbi.nlm.nih.gov/34226400/
In vivo activity:	Histopathological investigation of the hepatic tissues for the normal control group showed the presence of normal hepatocytes and central vein. In comparison to this, liver specimen for 5-FU control group rats were characterized by marked reactive changes, suggestive of hydropic degeneration (HD) of the hepatocytes and focal necrosis at the central vein zone along with the disruption of the hepatic central vein (HCV). The pre- and co-treatment with GA (gentisic acid) resulted in a dose-dependent amelioration of these histopathological alterations. As shown in Figure 3, GA administration at doses of 30 and 100 mg/kg body weight showed moderate and marked improvement, respectively, in the histopathological alterations of the liver tissues. Reference: Turk J Pharm Sci. 2021 Jun 18;18(3):332-338. https://pubmed.ncbi.nlm.nih.gov/34157823/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	65.5	424.99
	Ethanol	31.0	201.14
	Water	15.0	97.33

Preparing Stock Solutions

The following data is based on the product molecular weight 154.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Kang MJ, Choi W, Yoo SH, Nam SW, Shin PG, Kim KK, Kim GD. Modulation of Inflammatory Pathways and Adipogenesis by the Action of Gentisic Acid in RAW 264.7 and 3T3-L1 Cell Lines. J Microbiol Biotechnol. 2021 Aug 28;31(8):1079-1087. doi: 10.4014/jmb.2105.05004. PMID: 34226400. 2. Mechchate H, Es-Safi I, Mohamed Al Kamaly O, Bousta D. Insight into Gentisic Acid Antidiabetic Potential Using In Vitro and In Silico Approaches. Molecules. 2021 Mar 30;26(7):1932. doi: 10.3390/molecules26071932. PMID: 33808152; PMCID: PMC8037080. 3. Dong X, Zhang Q, Zeng F, Cai M, Ding D. The protective effect of gentisic acid on rheumatoid arthritis via the RAF/ERK signaling pathway. J Orthop Surg Res. 2022 Feb 20;17(1):109. doi: 10.1186/s13018-022-03006-7. PMID: 35184721; PMCID: PMC8859882. 4. Pujari RR, Bandawane DD. Hepatoprotective Activity of Gentisic Acid on 5-Fluorouracil-induced Hepatotoxicity in Wistar Rats. Turk J Pharm Sci. 2021 Jun 18;18(3):332-338. doi: 10.4274/tjps.galenos.2020.95870. PMID: 34157823; PMCID: PMC8231324.
In vitro protocol:	1. Kang MJ, Choi W, Yoo SH, Nam SW, Shin PG, Kim KK, Kim GD. Modulation of Inflammatory Pathways and Adipogenesis by the Action of Gentisic Acid in RAW 264.7 and 3T3-L1 Cell Lines. J Microbiol Biotechnol. 2021 Aug 28;31(8):1079-1087. doi: 10.4014/jmb.2105.05004. PMID: 34226400. 2. Mechchate H, Es-Safi I, Mohamed Al Kamaly O, Bousta D. Insight into Gentisic Acid Antidiabetic Potential Using In Vitro and In Silico Approaches. Molecules. 2021 Mar 30;26(7):1932. doi: 10.3390/molecules26071932. PMID: 33808152; PMCID: PMC8037080.
In vivo protocol:	1. Dong X, Zhang Q, Zeng F, Cai M, Ding D. The protective effect of gentisic acid on rheumatoid arthritis via the RAF/ERK signaling pathway. J Orthop Surg Res. 2022 Feb 20;17(1):109. doi: 10.1186/s13018-022-03006-7. PMID: 35184721; PMCID: PMC8859882. 2. Pujari RR, Bandawane DD. Hepatoprotective Activity of Gentisic Acid on 5-Fluorouracil-induced Hepatotoxicity in Wistar Rats. Turk J Pharm Sci. 2021 Jun 18;18(3):332-338. doi: 10.4274/tjps.galenos.2020.95870. PMID: 34157823; PMCID: PMC8231324.

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1. Kang MJ, Choi W, Yoo SH, Nam SW, Shin PG, Kim KK, Kim GD. Modulation of Inflammatory Pathways and Adipogenesis by the Action of Gentisic Acid in RAW 264.7 and 3T3-L1 Cell Lines. J Microbiol Biotechnol. 2021 Aug 28;31(8):1079-1087. doi: 10.4014/jmb.2105.05004. PMID: 34226400.
2. Mechchate H, Es-Safi I, Mohamed Al Kamaly O, Bousta D. Insight into Gentisic Acid Antidiabetic Potential Using In Vitro and In Silico Approaches. Molecules. 2021 Mar 30;26(7):1932. doi: 10.3390/molecules26071932. PMID: 33808152; PMCID: PMC8037080.
3. Dong X, Zhang Q, Zeng F, Cai M, Ding D. The protective effect of gentisic acid on rheumatoid arthritis via the RAF/ERK signaling pathway. J Orthop Surg Res. 2022 Feb 20;17(1):109. doi: 10.1186/s13018-022-03006-7. PMID: 35184721; PMCID: PMC8859882.
4. Pujari RR, Bandawane DD. Hepatoprotective Activity of Gentisic Acid on 5-Fluorouracil-induced Hepatotoxicity in Wistar Rats. Turk J Pharm Sci. 2021 Jun 18;18(3):332-338. doi: 10.4274/tjps.galenos.2020.95870. PMID: 34157823; PMCID: PMC8231324.

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