5-Methoxysalicylic Acid CAS 2612-02-4
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5-Methoxysalicylic Acid CAS 2612-02-4

5-Methoxysalicylic Acid CAS 2612-02-4

Product Code: BM-2-5-400
CAS number: 2612-02-4
Molecular formula: C8H8O4
Molecular weight: 168.15
EINECS number:220-037-8
MDL No.: MFCD00002459
Hs code: 29189900
Analysis items: HPLC>99.0%, LC-MS
Main market: USA, Australia, Brazil, Japan, Germany, Indonesia, UK, New Zealand , Canada etc.
Manufacturer: BLOOM TECH Changzhou Factory
Technology service: R&D Dept.-4

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5-Methoxysalicylic Acid (CAS 2612-02-4) is an organic compound derived from salicylic acid, featuring a methoxy (–OCH₃) group at the fifth position of the aromatic ring. This white to off-white crystalline powder is sparingly soluble in water but dissolves well in organic solvents like ethanol and dimethyl sulfoxide (DMSO). It serves as a key intermediate in pharmaceutical synthesis, particularly in the production of nonsteroidal anti-inflammatory drugs (NSAIDs) and dermatological agents due to its structural similarity to aspirin.

 

In research, It is studied for its potential antioxidant, anti-inflammatory, and antimicrobial properties. It also acts as a precursor in organic chemistry for synthesizing more complex molecules, including dyes and fragrances. Additionally, its role in plant biochemistry has been explored, as it may influence phenolic metabolism.

 

Handling requires caution, as it can cause skin and eye irritation. Proper storage in a cool, dry place is essential to maintain stability. Regulatory status varies by region, but it is generally classified as a laboratory chemical rather than a controlled substance.

Produnct Introduction

 

5-Methoxysalicylic Acid CAS 2612-02-4 | Shaanxi BLOOM Tech Co., Ltd

5-Methoxysalicylic Acid CAS 2612-02-4 | Shaanxi BLOOM Tech Co., Ltd

Chemical Formula

C8H8O4

Exact Mass

168.04

Molecular Weight

168.15

m/z

168.04 (100.0%), 169.05 (8.7%)

Elemental Analysis

C, 57.14; H, 4.80; O, 38.06

Applications | Shaanxi BLOOM Tech Co., Ltd

 

Matrix for MALDI-MS Analysis

 

When combined with spermine, 5-Methoxysalicylic acid serves as an effective matrix for the Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) analysis of oligonucleotides.

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Improved Sensitivity and Resolution

The use of 5-MeOSA with spermine enhances the sensitivity and resolution of MALDI-MS analysis, making it possible to detect and differentiate oligonucleotides with high accuracy.

Enhanced Conductivity

The presence of spermine in the matrix improves the electrical conductivity of the crystal formed during the MALDI process. This conductivity is crucial for the efficient desorption and ionization of analytes, leading to better mass spectrometry results.

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Compatibility with Various Oligonucleotides

The matrix formed by 5-MeOSA and spermine is compatible with a wide range of oligonucleotides, including those with different lengths, base compositions, and modifications. This makes it a versatile tool for oligonucleotide analysis.

Reduced Background Noise

The use of this matrix combination can help reduce background noise in the mass spectrometry spectrum, making it easier to identify and quantify the analytes of interest.

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Oligonucleotides are short, single-stranded segments of nucleic acids, composed of a sequence of nucleotide units typically ranging from 2 to 200 bases in length. These nucleotide units consist of a phosphate group, a sugar moiety (deoxyribose in DNA or ribose in RNA), and a nitrogenous base (adenine, thymine/uracil, cytosine, or guanine). Oligonucleotides play pivotal roles in the biology of organisms, particularly in genetic information storage and expression.

In research and biotechnology, oligonucleotides serve as vital tools for various applications. They are frequently utilized as primers in polymerase chain reaction (PCR) experiments, enabling the amplification of specific DNA sequences. As probes, they can hybridize with complementary DNA or RNA sequences, facilitating the detection and analysis of genes and gene expression patterns.

Oligonucleotides are also essential components in gene therapy, where they can function as antisense oligonucleotides to block the expression of specific genes or as aptamers to bind and regulate proteins. Furthermore, they serve as building blocks for the synthesis of synthetic genes and gene constructs, playing a crucial role in genetic engineering and synthetic biology.

The synthesis of oligonucleotides typically involves the chemical assembly of nucleotide units through phosphoramidite chemistry, a process that allows for the precise incorporation of desired base sequences. This high degree of specificity and customizability makes oligonucleotides indispensable for a wide range of research and diagnostic applications.

In summary, oligonucleotides are fundamental components of nucleic acids that have diverse and crucial roles in biology and biotechnology. Their use as primers, probes, gene therapy agents, and synthetic gene building blocks underscores their importance in advancing scientific research and medical innovations.

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Scientific Research and Drug Discovery

Due to its unique properties, it is used in scientific studies to evaluate MALDI matrix/solvent combinations for intact spore mass spectrometry of various species, such as Fusarium. It contributes to the advancement of analytical chemistry and biotechnology by enabling more precise and efficient mass spectrometry analyses.

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Intact Spore Analysis

Intact spore mass spectrometry is a technique used to analyze the mass of spores without prior disruption or extraction. This method provides valuable information about the composition and structure of spores, which is crucial for understanding their survival mechanisms, germination processes, and potential as biological indicators.

MALDI Matrix Evaluation

In scientific studies, different MALDI matrices and solvents are evaluated to determine the most effective combination for intact spore analysis. 5-MeOSA, due to its ability to form stable crystals with analytes and enhance their desorption and ionization, is often included in these evaluations.

5-Methoxysalicylic Acid Matrix | Shaanxi BLOOM Tech Co., Ltd
5-Methoxysalicylic Acid Species | Shaanxi BLOOM Tech Co., Ltd

Compatibility with Fusarium Species

The matrix formed by 5-MeOSA has been shown to be compatible with spores of various species, including Fusarium. This compatibility is essential for obtaining accurate and reproducible mass spectrometry results.

Improved Sensitivity and Resolution

The use of 5-MeOSA as a MALDI matrix can improve the sensitivity and resolution of intact spore mass spectrometry, making it easier to detect and differentiate spores of different species and strains.

Insight into Sporulation Mechanisms

By evaluating different MALDI matrix/solvent combinations using 5-MeOSA, scientists can gain insights into the sporulation mechanisms of various species, including how spores are formed, their composition, and their stability.

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Overall, the use in scientific studies to evaluate MALDI matrix/solvent combinations for intact spore mass spectrometry of species like Fusarium demonstrates its versatility and potential in the field of analytical chemistry and biotechnology.

Development prospects

5-Methoxysalicylic Acid  is a highly active derivative of salicylic acid, with core values in six directions: anti-inflammatory and antioxidant, keratin regulation, whitening and spot removal, drug absorption promotion, mass spectrometry matrix, and organic synthesis blocks. It covers six major fields: pharmaceutical intermediates, cosmetic active materials, analytical chemical reagents, fine chemical synthesis, plant physiology research, and food flavorings. It is a key raw material for daily chemical whitening, anti-inflammatory drugs, mass spectrometry analysis, and green synthesis.

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Intermediate of anti-inflammatory and analgesic drugs

5-MeOSA exerts potent anti-inflammatory, analgesic, and antipyretic effects by inhibiting cyclooxygenase (COX-1/COX-2), reducing prostaglandin E2 (PGE2) synthesis, and blocking inflammatory signaling pathways (NF - κ B, MAPK); The anti-inflammatory activity is superior to aspirin and salicylic acid, and the irritation is lower.
Synthesis of nonsteroidal anti-inflammatory drugs (NSAIDs): 5-methoxysalicylate/amide derivatives are synthesized by esterification, amidation, and condensation of 5-meOSA, which are used for the treatment of rheumatoid arthritis, osteoarthritis, gout, and postoperative pain;

The analgesic effect is twice that of aspirin, the anti-inflammatory effect is 1.8 times that of aspirin, and the gastrointestinal irritation is reduced by 50%.
Skin anti-inflammatory external medication: 5 MeOSA is directly used as an active ingredient for the treatment of dermatitis, eczema, acne, psoriasis, and UV sunburn; Inhibit skin inflammation, reduce redness, swelling, itching, promote skin repair, reduce pigmentation, mild and non irritating, suitable for sensitive skin.
Oral anti-inflammatory preparations: used for the treatment of oral ulcers, gingivitis, and periodontitis, inhibiting oral bacteria, reducing inflammatory pain, and promoting mucosal repair.

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Drug absorption enhancer

5-MeOSA is an efficient mucosal absorption enhancer that can reversibly disrupt the tight junctions between mucosal epithelial cells, increase cell membrane fluidity, and inhibit drug efflux transporters (P-gp), significantly improving the efficiency of drug transdermal, mucosal, and intestinal absorption.
Rectal administration promotes absorption: When used in combination with drugs such as cefoxitin sodium, bleomycin, insulin, etc., it significantly improves the rectal absorption efficiency of drugs (2-5 times higher), increases lymphatic transport, and reduces first pass effects.

It is used for the development of rectal administration formulations for antibiotics, peptides, and protein drugs.
Transdermal administration to promote absorption: it is added to transdermal patches, gel, and creams to improve the skin permeability of drugs (3 – 10 times), prolong the action time, and reduce the dosage of drugs. It is used for transdermal preparations of analgesia, hormones, and antihypertensive drugs.
Oral medication promotes absorption: When used in combination with poorly soluble drugs and drugs with low bioavailability, it enhances intestinal absorption, improves bioavailability, and reduces individual differences.

5-Methoxysalicylic Acid Used | Shaanxi BLOOM Tech Co., Ltd
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Hypoglycemic and Metabolic Regulating Drugs

5-MeOSA exerts hypoglycemic, lipid-lowering, and metabolic syndrome improving effects by activating the AMPK pathway, inhibiting hepatic gluconeogenesis, promoting peripheral tissue glucose uptake, and improving insulin resistance.
Treatment of type 2 diabetes: reduce fasting blood glucose (15% – 20%), improve insulin sensitivity, reduce insulin level, and reduce liver glycogen output; No risk of hypoglycemia, non-toxic to liver and kidney, suitable for diabetes patients with obesity/hyperlipidemia.
Metabolic syndrome intervention: reduce triglycerides, total cholesterol, increase HDL-C, reduce visceral fat deposition, and improve vascular endothelial function.

Antioxidant and hepatoprotective drugs

5-Methoxysalicylic Acid directly scavenges free radicals (superoxide anions, hydroxyl radicals, lipid peroxides), enhances endogenous antioxidant enzyme (SOD, GSH-PX, CAT) activity, reduces MDA content, alleviates oxidative stress damage, and inhibits liver cell inflammation and fibrosis.
Liver injury protection: Used as an adjuvant therapy for drug-induced liver injury, alcoholic fatty liver, viral hepatitis, and liver fibrosis, reducing liver cell damage, lowering transaminase levels, improving liver function, and delaying the progression of liver fibrosis.
Neuroprotection: Inhibits oxidative stress in nerve cells, reduces neuronal apoptosis, improves cognitive function, and is used as an adjuvant therapy for Alzheimer's disease, Parkinson's disease, and stroke.

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5-Methoxysalicylic Acid Other | Shaanxi BLOOM Tech Co., Ltd

Other Medical Uses

Antibacterial drugs: have moderate inhibitory activity (MIC=32-128 μ g/mL) against Staphylococcus aureus, Escherichia coli, Salmonella, Propionibacterium acnes, and Candida albicans, and are used for the treatment of skin infections, oral infections, and vaginitis.
Antithrombotic drugs: inhibit platelet aggregation, reduce blood viscosity, improve microcirculation, used as adjuvant therapy for thrombotic diseases and cardiovascular and cerebrovascular diseases.
Antiallergic drugs: inhibit histamine release, block allergic signaling pathways, alleviate allergic reactions, used for the treatment of allergic dermatitis, urticaria, and allergic rhinitis.

whitening and spot removal

Inhibition of tyrosinase activity: competitively binds to the active site of tyrosinase, blocks the key step of melanin synthesis, with an inhibition rate of ≥ 90% (concentration 2%), and the effect is twice that of salicylic acid and 1.5 times that of nicotinamide.
Blocking melanin transport: Inhibiting the transport of melanosomes to stratum corneum cells and reducing epidermal melanin deposition.
Accelerate melanin metabolism: promote the metabolism of the stratum corneum, accelerate the shedding of melanin containing dead skin cells, and fade pigmentation and acne scars.
Antioxidant and anti darkening: Clearing free radicals, inhibiting UV induced oxidative stress, reducing pigmentation, brightening skin tone, and improving dullness and yellowing.

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Frequently Asked Questions
 
 

What is 5 methoxy salicylic acid?

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5-methoxysalicylic acid is a methoxysalicylic acid that is salicylic acid which is carrying a methoxy group at position 5. It has a role as a bacterial metabolite and a human urinary metabolite.

Why isn't Gentisic Acid, which also has two oxygen substitutions?

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It is a "chemical variant" of gentian acid (2,5-dihydroxybenzoic acid) - replacing the hydrogen of one of the hydroxyl groups (- OH) with a methoxy group (- OCH3), which makes it chemically distinct from gentian acid. According to the classification of HMDB, one of its aliases is "5-O-Methylgentisic acid", also known as "5-O-Methylgentic acid". This means that its core skeleton is Gentisic Acid (a phenolic acid found in plants and humans), but it undergoes methylation on the hydroxyl group (- OH) at position 5, becoming methoxy (- OCH3). This small chemical modification - sealing an active phenolic hydroxyl group into an inert ether bond - greatly alters the physical and chemical properties of the molecule. It loses the antioxidant and metal chelating abilities of gentian acid (as the phenolic hydroxyl group is the active site), but gains the special UV absorption and charge transfer properties required as a MALDI matrix.

Salicylic acid is toxic, what role does its "methylated" cousin play in organisms?

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It is not a "toxin" in living organisms, but a normal "urinary metabolite" that comes from the body's metabolism of dietary components such as tea and spices. HMDB explicitly lists it as "Human Urinary Metabolite", which means it can be detected in normal human urine. It not only exists in the human body, but also exists as a bacterial metabolite in the microbial metabolism of nature. In addition, it is also one of the components in the Castoreum secretion of mature beavers. This indicates that the molecule has high biocompatibility and is not a foreign harmful substance. This is also one of the reasons why it can be widely used in in vitro diagnostics (IVD) and biological analysis reagents.

 

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