11480

Azelainsäure

technical, ~85% (GC)

• Synonym(e): Nonandisäure
• Lineare Formel: HO₂C(CH₂)₇CO₂H
• CAS-Nummer: 123-99-9
• Molekulargewicht: 188.22
• UNSPSC Code: 12352100
• NACRES: NA.22
• PubChem Substance ID: 329749451
• EC Number: 204-669-1
• Beilstein/REAXYS Number: 1101094
• MDL number: MFCD00004432
• Assay: ~85% (GC)

Eigenschaften

• vapor density: 6.5 (vs air)
• Quality Segment: 200
• vapor pressure: <1 mmHg ( 20 °C)
• grade: technical
• assay: ~85% (GC)
• bp: 286 °C/100 mmHg (lit.)
• mp: 109-111 °C (lit.)
• functional group: carboxylic acid
• SMILES string: OC(=O)CCCCCCCC(O)=O
• InChI: 1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
• InChI key: BDJRBEYXGGNYIS-UHFFFAOYSA-N

Beschreibung

General description

Azelaic acid (Nonanedioic acid) is a naturally occurring saturated, nonphenolic compound isolated from cultures Pityrosporum ovale[1]. It is a therapeutic agent with well-known antibacterial properties[2].

Application

• A phase 3 randomized, double-blind, vehicle-controlled trial of azelaic acid foam 15% in the treatment of papulopustular rosacea: This study evaluates the efficacy and safety of a 15% azelaic acid foam in treating rosacea, demonstrating significant improvements in disease severity (Draelos et al., 2015).
• Comparison of the characteristics of transfersomes and protransfersomes containing azelaic acid: This research compares the properties of transfersome formulations with azelaic acid, highlighting their potential for enhanced delivery in dermatological applications (Rahmi and Pangesti, 2018).
• Enhancing the bioconversion of azelaic acid to its derivatives by response surface methodology: This article discusses optimizing the production of azelaic acid derivatives, which are crucial for cosmetic and pharmaceutical applications (Khairudin et al., 2018).
• Azelaic acid: a bio-based building block for biodegradable polymers: The study explores azelaic acid as a sustainable precursor for producing biodegradable polymers, pertinent to material science (Todea et al., 2021).
• Preparation and evaluation of azelaic acid topical microemulsion formulation: in vitro and in vivo study: This research presents a microemulsion formulation of azelaic acid, assessing its stability and skin permeability, critical for topical therapeutic applications (Hung et al., 2021).

Biochem/physiol Actions

Azelaic acid is a potent inhibitor of 5α-reductase activity[3]. It is a reversible competitive inhibitor of thioredoxin reductase in human melanoma cells[4].

Sicherheitshinweise

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319
• pcodes: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 1
• flash_point_f: 410.0 °F - closed cup
• flash_point_c: 210 °C - closed cup
• ppe: Eyeshields, Gloves, type N95 (US)