2169-28-0

Basic information

• Product Name: 3-HYDROXY-2-METHOXYBENZOIC ACID
• Synonyms: 3-HYDROXY-2-METHOXYBENZOIC ACID
• CAS NO: 2169-28-0
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 2169-28-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 346.096 °C at 760 mmHg
• Flash Point: 146.026 °C
• Appearance: /
• Density: 1.352 g/cm³
• CAS DataBase Reference: 3-HYDROXY-2-METHOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-2-METHOXYBENZOIC ACID(2169-28-0)
• EPA Substance Registry System: 3-HYDROXY-2-METHOXYBENZOIC ACID(2169-28-0)

Safety Data

• Hazardous Substances Data: 2169-28-0(Hazardous Substances Data)

Usage

Description

3-Hydroxy-2-methoxybenzoic Acid, a naturally occurring compound, is an organic compound with the molecular formula C8H8O5. It is characterized by the presence of a hydroxyl group (-OH) at the 3rd position and a methoxy group (-OCH3) at the 2nd position on a benzoic acid backbone. 3-HYDROXY-2-METHOXYBENZOIC ACID is known for its potential applications in various fields due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-2-methoxybenzoic Acid is used as a key intermediate in the synthesis of isoquinoline derivatives, which are known as protein kinase inhibitors. These inhibitors play a crucial role in the development of drugs targeting various diseases, including cancer and other disorders related to the overactivation of protein kinases.
In the preparation of isoquinoline derivatives, 3-Hydroxy-2-methoxybenzoic Acid serves as a building block, contributing to the formation of the final compound with potential therapeutic applications. The compound's unique structure allows for the development of isoquinoline derivatives with specific inhibitory properties, making it a valuable component in the pharmaceutical industry's pursuit of novel and effective treatments for various diseases.

Upstream product

• 866528-90-7 2-methoxy-3-(toluene-4-sulfonyloxy)-benzoic acid methyl ester 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 90-05-1 2-methoxy-phenol 
• 579-75-9 2-Methoxybenzoic acid 

Downstream Products

• 2169-25-7 methyl 3′-hydroxy-2′-methoxybenzoate 

Relevant articles and documents

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Demethoxylation and hydroxylation of methoxy- and hydroxybenzoic acids by OH-radicals. Processes of potential importance for food irradiation

The hydroxylation process for methoxy- and hydroxy-benzoic acids (MBA, HBA) induced by γ-radiation is compared. 2-, 3-, and 4-methoxybenzoic acid as well as 3-hydroxybenzoic acid have been irradiated in N2O and aerated solutions up to 1.5 kGy. The products were analyzed by HPLC. The results for 2- and 4-HBA have been taken from literature data. The OH·-adduct distribution is generally the same for the hydroxy- as well as for the methoxy-benzoic acid isomers. With both 4-HBA and 4-MBA more than 65% C3-adducts and about 15% C4-adducts are formed, which could be proved by their reactions with K3 Fe(CN)6. Oxidation of the nonipso-adducts of 3-HBA and 3-MBA results in 84 and 87% of the corresponding phenols. Whereas in N2O-saturated solutions only part of the OH·-radicals leads to substrate decomposition, in the presence of air, the degradation of both kinds of compounds is equivalent to [OH·]. The nonipso OH·-adducts of the HBAs are converted into 68-77% hydroxylation products. With the MBAs, the hydroxylation process is ≤10%. This is attributed to different decay pathways of the peroxyl radicals, intermediates formed by O2 addition to the OH·-adducts. The hydroxyperoxycyclohexadienyl radicals of the HBAs decay mainly by HO2· elimination to the corresponding phenols, those of the MBAs decay predominantly by fragmentation of the benzene ring, yielding to nonidentified aliphatic products. The replacement of -OCH3 by -OH is practically not influenced by the presence of oxygen, it increases in the sequence 3-MBA 4-MBA 2-MBA. For 2-MBA, yields of more than 15% are obtained. Both processes, hydroxylation as well as demethoxylation, might be of importance for the recognition of radiolytical changes in foodstuff.