Diethyl azelate

• CAS: 624-17-9
• Catalog Number: ACM624179
• Category: Main Products
• Molecular Weight: 244.33
• Molecular Formula: C2H5O2C(CH2)7CO2C2H5
• Synonyms: Diethyl nonanedioate
• SMILES: CCOC(=O)CCCCCCCC(=O)OCC
• InChI: 1S/C13H24O4/c1-3-16-12(14)10-8-6-5-7-9-11-13(15)17-4-2/h3-11H2,1-2H3
• InChI Key: CQMYCPZZIPXILQ-UHFFFAOYSA-N
• Boiling Point: 172 °C/18 mmHg (lit.)
• Melting Point: -16--15.8 °C (lit.)
• Flash Point: >113 °C
• Density: 0.973 g/mL at 25 °C (lit.)
• Application: This product is suitable for scientific research.
• Assay: 90%
• EC Number: 210-833-3
• Features And Benefits: 1. High quality products; 2. Fast delivery; 3. Additional products can be ordered, please contact us for details
• Grade: technical grade
• MDL Number: MFCD00009218
• NACRES: NA.23
• PubChem ID: 24847617
• Quality Level: 100
• Refractive Index: n20/D 1.435 (lit.)

Case Study

Diethyl Azelate Mixtures as Novel Non-Opioid Analgesic Agents

Izbicka, Elzbieta, et al. Cureus 17.3 (2025).

Diethyl azelate, a medium-chain fatty acid ester that functions as a membrane-active immunomodulator, offers a novel non-opioid approach to analgesia through reversible alteration of plasma membrane fluidity and subsequent modulation of inflammatory signaling cascades involving phospholipase D and phospholipase A2. Experimental Protocol: Cutaneous mechanical sensitivity assays using standardized Von Frey monofilaments were employed to quantify analgesic activity in a single human subject across systematic self-experimentation. Diethyl azelate was evaluated alone and in binary, ternary, and quaternary mixtures with dimethyl sulfoxide, limonene, alpha-pinene, beta-pinene, menthol, and 32 additional terpenes. Over-the-counter analgesics served as positive controls.
Performance Evaluation: Binary mixtures of diethyl azelate and dimethyl sulfoxide displayed pronounced and unexpected synergy, with the maximum analgesic duration of 72 hours achieved at an equimolar ratio (78% diethyl azelate and 22% dimethyl sulfoxide)-far exceeding the 4-hour duration of either component alone. Adding limonene, alpha-pinene, or menthol at low concentrations (0.1-2%) produced additional levels of synergy, with a four-component mixture of diethyl azelate, dimethyl sulfoxide, limonene, and menthol yielding the greatest overall potency. Importantly, dimethyl sulfoxide and limonene both exhibited bell-shaped dose-response curves, demonstrating that their effects extend beyond simple facilitation of tissue penetration and instead involve complex multi-target interactions. Among related azelaic acid diesters, only diethyl azelate displayed this synergistic behavior.

Diethyl Azelate for Brown Recluse Spider Bite Treatment: Orphan Drug Indication

Streeper, Robert T., et al. in vivo 36.1 (2022): 86-93.

Brown recluse spider envenomation (loxoscelism) releases hemolytic and cytotoxic phospholipase D toxin into the wound, potentially causing severe tissue necrosis and systemic effects including rapid fatality. Diethyl azelate, a plasma membrane fluidizer with broad immunomodulatory activities, was investigated as a potential emergency treatment.
Experimental Protocol: Two accidental brown recluse spider bites in a human subject-one on the forearm and another on the neck occurring approximately one year apart-were treated with topical diethyl azelate applied at 4-8 hour intervals for 14 days, with wound progression documented photographically and analyzed quantitatively using image processing. In vitro experiments evaluated the effects of diethyl azelate on hemolysis induced by Loxosceles reclusa crude venom and recombinant phospholipase D using human erythrocyte suspensions over 60-minute incubations.
Performance Evaluation: Topical diethyl azelate completely resolved all consequences of brown recluse envenomation within 14 days in both human cases, with inflammatory zones visibly disappearing by 72 hours and no complications. In vitro, diethyl azelate inhibited hemolysis caused by both crude venom and recombinant phospholipase D in a non-linear dose-dependent manner, with complete inhibition observed at 5 mM for crude venom and 122 mM for the recombinant enzyme. Preincubation of diethyl azelate with venom prior to erythrocyte exposure produced superior inhibition compared to preincubation with erythrocytes, suggesting direct physicochemical interaction with the phospholipase D enzyme.

Diethyl Azelate as Prodrug Strategy for Enhanced Transdermal Delivery of Azelaic Acid

Al-Marabeh, Sara, et al. Pharmaceutical Development and Technology 22.4 (2017): 578-586.

\Azelaic acid is an established topical agent for acne vulgaris with antibacterial, anti-inflammatory, and antityrosinase activities. However, at physiological skin pH, approximately 90% of the applied dose exists in the ionized form, limiting percutaneous absorption to only 3-5% and necessitating high concentrations (up to 20%) that frequently cause local irritation. A prodrug strategy to enhance azelaic acid skin delivery was reported in this work.
Experimental Protocol: The diethyl ester of azelaic acid was synthesized via acid-catalyzed esterification. Chemical stability was assessed under acidic, basic, and oxidative conditions. Enzymatic hydrolysis rates were quantified using porcine liver esterase and fresh human skin homogenate via the pH-stat titration method, with skin viability after frozen storage also evaluated. In vitro diffusion was compared through synthetic silicone membrane and trypsin-isolated human stratum corneum using vertical Franz-diffusion cells with ethanol/phosphate buffer donor media. A desorption study from stratum corneum was conducted over 26 hours to evaluate reservoir behavior. Antimicrobial activity against Staphylococcus aureus and Propionibacterium acnes was assessed by broth microdilution.
Performance Evaluation: Diethyl azelate exhibited substantially higher lipophilicity than the parent acid, with a predicted log P of 3.77 versus approximately 2.0, and was resistant to chemical hydrolysis under all tested conditions. Through silicone membrane, the prodrug showed approximately three-fold greater diffusion compared to azelaic acid. However, the opposite trend was observed with human stratum corneum: diethyl azelate permeated weakly (6.2% of the applied dose) compared to azelaic acid (48.4%), consistent with extensive retention within the stratum corneum lipid and keratin matrix.

Custom Q&A

What is the molecular formula of Diethyl azelate?

The molecular formula of Diethyl azelate is C2H5O2C(CH2)7CO2C2H5.

What is the boiling point of Diethyl azelate?

The boiling point of Diethyl azelate is 172 °C/18 mmHg.

What is the purity of Diethyl azelate?

The purity of Diethyl azelate is 95%.

What is the density of Diethyl azelate at 25 °C?

The density of Diethyl azelate is 0.973 g/mL at 25 °C.

What is the application of Diethyl azelate?

This product is suitable for scientific research.

What are the features and benefits of Diethyl azelate?

The features and benefits are high quality products, fast delivery, and additional products can be ordered.

What is the grade of Diethyl azelate?

The grade of Diethyl azelate is technical grade.

What is the PubChemID of Diethyl azelate?

The PubChemID of Diethyl azelate is 24847617.

What is the refractive index of Diethyl azelate?

The refractive index of Diethyl azelate is n20/D 1.435.

What is the EC Number of Diethyl azelate?

The EC Number of Diethyl azelate is 210-833-3.