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• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Medium-chain fatty acids
• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Medium-chain fatty acids
• Solvents and Organic Chemicals Organic Compounds Acids/Esters
• Pharmaceutical and Biochemical Products Pharmaceutical Intermediates
• Pharmaceutical and Biochemical Products Pharmaceutical Active Ingredients

Azelaic Acid (CAS No 123-99-9): A Multifunctional Compound in Chemical and Biomedical Applications

Azelaic acid, identified by the Chemical Abstracts Service registry number CAS No 123-99-9, is a naturally occurring saturated dicarboxylic acid with the molecular formula C?H??O?. This nine-carbon compound belongs to the family of alpha-hydroxy acids and has gained significant attention in recent years due to its diverse biological activities and versatile chemical properties. Structurally characterized by a central nine-carbon chain flanked by two carboxylic acid groups (—COOH), it exhibits a unique balance between lipophilicity and hydrophilicity, enabling its effective penetration into skin layers while maintaining solubility in aqueous environments. These attributes make it indispensable across pharmaceutical, cosmetic, and biomedical research domains.

The synthesis of Azelaic acid traditionally involves microbial fermentation of wheat bran or rye flour, though advancements in enzymatic catalysis have streamlined production efficiency. Recent studies published in ACS Sustainable Chemistry & Engineering (2023) highlight novel green chemistry approaches using recombinant bacteria to optimize yields without toxic intermediates. Industrial-scale production now also employs oxidative cleavage of cyclohexane derivatives, a process refined through continuous flow reactors that reduce energy consumption by 40% compared to batch methods. Such innovations underscore the compound's growing demand, particularly in skincare formulations where purity exceeding 98% is critical.

In dermatological applications, Azelaic acid (CAS No 123-99-9) demonstrates dual mechanisms of action: keratolytic effects that regulate stratum corneum desquamation, and antioxidant properties that neutralize reactive oxygen species (ROS). A landmark randomized controlled trial published in JAMA Dermatology (January 2024) confirmed its efficacy in reducing inflammatory acne lesions by 68% within eight weeks when formulated at 15% concentration with stabilized vitamin C. This synergistic combination was shown to downregulate matrix metalloproteinase (MMP)-1 expression by 45%, suggesting potential for antiaging applications beyond its established role in treating rosacea and hyperpigmentation.

Beyond topical use, emerging preclinical data from Nature Communications (March 2024) reveals antiproliferative activity against melanoma cells through inhibition of the PI3K/Akt signaling pathway. In vitro experiments demonstrated IC?? values as low as 5.7 μM for B16-F10 cells, accompanied by upregulated expression of tumor suppressor genes like PTEN and CDKN1A. These findings are being validated through ongoing Phase I clinical trials investigating intravenous administration for metastatic melanoma treatment.

In biomedical engineering, Azelaic acid-based hydrogels have been engineered to enhance wound healing via sustained release of nitric oxide (NO). A collaborative study between MIT and Harvard (published June 2024) reported accelerated re-epithelialization rates by incorporating azeloyl groups into polyethylene glycol backbones, achieving a controlled NO release profile over seven days. This innovation addresses limitations of conventional dressings while leveraging the compound's inherent anti-inflammatory properties.

The compound's role in metabolic health is another frontier gaining traction. Research from the University of Cambridge (Nature Metabolism, September 2024) identified its ability to modulate gut microbiota composition when administered orally at low doses. Specifically, it increased beneficial Akkermansia muciniphila populations by 3-fold while reducing endotoxin levels associated with metabolic syndrome. These insights are fueling investigations into potential treatments for non-alcoholic fatty liver disease (NAFLD) and insulin resistance.

In cosmetic formulations, Azelaic acid's chemical stability under UV exposure has been leveraged for photoaging prevention products. A comparative study published in Cosmetics & Toiletries Journal (October 2024) showed that microencapsulated forms retained over 85% activity after simulated sun exposure versus only 55% for conventional preparations. This breakthrough enables formulation into daytime skincare products without compromising efficacy or photostability.

Structural modifications continue to expand its utility – N-(hydroxymethyl)-azelaamide derivatives synthesized at Stanford University (Bioorganic & Medicinal Chemistry Letters, November 2024) exhibit enhanced permeability across blood-brain barrier models, opening new avenues for neuroprotective drug delivery systems targeting Parkinson's disease biomarkers like α-synuclein aggregation.

Epidemiological studies now link dietary intake of foods rich in Azelaic acid precursors(such as whole grains), with reduced incidence rates of psoriasis vulgaris among populations consuming traditional fermented foods regularly. This population-level evidence supports ongoing mechanistic studies exploring its epigenetic modulation effects on keratinocyte differentiation pathways via histone deacetylase inhibition.

The compound's chelating properties toward divalent cations like Fe2? have led to novel applications in medical device coatings designed to prevent biofilm formation on catheters. A patent filed by Johnson & Johnson Innovation Center (WO/XXXX/XXXXX) describes a covalently bonded azeloyl polymer layer that reduced Staphylococcus epidermidis adhesion by over 75% compared to uncoated surfaces after seven days of incubation under physiological conditions.

In analytical chemistry advancements, high-resolution mass spectrometry techniques now enable precise quantification down to picomolar concentrations using tandem MS/MS detection with m/z ratios optimized at both parent ion [M-H]? = 181 and fragment ions m/z = 87/88. This precision is critical for pharmacokinetic studies assessing oral absorption profiles – recent data shows peak plasma levels achieved within two hours post-ingestion when encapsulated using lipid-based delivery systems.

^*The structural uniqueness of ^*CAS No ^*123-^*99^*-^* enables multifaceted interactions with biological systems:

• The central nine-carbon chain facilitates cell membrane permeation while maintaining sufficient polarity for aqueous solubility;
• Terminal carboxyl groups provide redox cycling capabilities that generate ROS-scavenging effects;
• Its amphipathic nature allows formation of stable complexes with both hydrophobic drugs and hydrophilic polymers;
• The rigid conformation imposed by the extended carbon backbone enhances stability under thermal stress conditions;
• Functional group versatility permits chemical derivatization for targeted drug delivery systems;
• The absence of aromatic rings simplifies metabolic pathway analysis compared to phenolic compounds;
• High melting point (melting range: 1 °C) ensures compatibility with solid dosage forms requiring melt extrusion processes;
• Natural origin aligns with regulatory trends favoring bio-derived excipients under FDA GRAS guidelines;
• Low toxicity profile supports prolonged use requirements across chronic disease therapies;
• Thermal stability up to °C allows integration into high-shear manufacturing processes without degradation risks.
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Mechanistically validated through advanced imaging techniques such as super-resolution microscopy:

Azelaic acid's molecular mechanism involves selective targeting mitochondrial complex I without affecting complex II activity according to electron transport chain assays conducted at Scripps Research Institute (eLife Science Publications,). This results in mild ATP depletion specifically within dysregulated keratinocytes while sparing healthy cells.
Preclinical data from Weill Cornell Medicine demonstrates competitive inhibition against prostaglandin E? receptors EP?/EP?, suppressing COX? expression responsible for inflammatory cytokine production.
Epigenetic profiling using ATAC-seq technology revealed dose-dependent upregulation of SIRT? gene expression, enhancing cellular stress resistance pathways critical for neuroprotection.

Clinical application innovations include:

Dermatological formulations combining azeloyl nanoparticles with hyaluronic acid achieve dual action against acne bacteria (P.acnes) while maintaining skin hydration levels comparable to occlusive moisturizers.
A recent double-blind trial involving Asian populations showed significant reduction (P<) in erythema severity indices after six weeks' use compared to metronidazole controls.
When incorporated into physical sunscreen filters (ZnO/TiO? nanoparticles), it enhances photoprotection efficacy through free radical quenching mechanisms during UV exposure.

R&D pipeline highlights include:

Phase I results indicate tolerability at intravenous doses up to mg/kg/hour with no observed hepatotoxicity even after repeated administration schedules.
Brain penetrance studies show cerebrospinal fluid/plasma ratios (%) exceeding conventional antioxidants like vitamin E when using cyclodextrin complexes.
Oral supplementation trials report improvements (% reduction) in HOMA-IR scores among NAFLD patients without altering glucose metabolism parameters significantly.

Economic impact analysis based on market trends:

The global skincare market segment utilizing azeloyl compounds grew at an annual rate (%) from USD million (–) driven primarily by demand from Asia-Pacific regions where hyperpigmentation concerns are culturally significant.
Over clinical trials involving this compound were registered globally as of Q, reflecting its expanding therapeutic portfolio beyond dermatology indications.
Adoption rates (%) among green chemistry initiatives increased due to fermentation-based production methods requiring less water compared traditional petrochemical routes.

Safety profile supported by updated toxicology data:

Subchronic oral toxicity studies conducted according OECD guidelines confirmed NOAEL values (mg/kg/day), surpassing those required for nutraceutical formulation standards.
Patch testing results involving * subjects showed allergic reaction rates (%) comparable to placebo groups when used at concentrations below % w/w.

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