11480

Azelaic acid

technical, ~85% (GC)

• Synonym(s): Nonanedioic acid
• Linear Formula: HO₂C(CH₂)₇CO₂H
• CAS Number: 123-99-9
• Molecular Weight: 188.22
• Beilstein: 1101094
• EC Number: 204-669-1
• MDL number: MFCD00004432
• UNSPSC Code: 12352100
• PubChem Substance ID: 329749451
• NACRES: NA.22

Properties

• vapor density: 6.5 (vs air)
• Quality Level: 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

Description

General description

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

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. It is a reversible competitive inhibitor of thioredoxin reductase in human melanoma cells.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319
• Precautionary Statements: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): 410.0 °F - closed cup
• Flash Point(C): 210 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves