Hexadecanedioic acid

Hexadecanedioic acid, also known as sebacic acid (CAS 118-93-7), is a saturated dicarboxylic acid with a 16-carbon aliphatic chain (HOOC-(CH₂)₁₄-COOH). It appears as a white, crystalline solid melting at 158 °C, soluble in polar organic solvents but sparingly soluble in water. The symmetrical carboxyl ends allow condensation reactions to synthesize high-melting nylon-6,10, polyesters, and polyamides. It is widely used industrially and as a food-grade additive (E 460), cosmetic ingredient, and lubricant additive with low toxicity. High-purity (>98%) hexadecanedioic acid is commercially available and utilized in polymer chemistry, materials science, and analytical reference standards.

Appearance

• White to off-white crystalline powder

• Odorless

• Slightly hygroscopic when stored in open air

• Melting point: 158 °C (decomposition commences ~170 °C)

Source

• Commercial suppliers: Sigma-Aldrich, TCI America, Alfa-Aesar, Lipo-Chem, Thermo-Fisher (research-grade)

• Laboratory synthesis: oxidation of hexadecane or 1-hexadecene via KMnO₄/NaOH or OsO₄/NaIO₄ routes

• Naturally occurring in minor amounts in certain plant oils and animal tissues

Molecular Weight and Structure

• Molecular formula: C₁₆H₃₂O₄

• Molecular weight: 276.42 g/mol

• IUPAC name: hexadecanedioic acid (sebacic acid)

• Chemical structure: HOOC-(CH₂)₁₄-COOH

• SMILES: O=C(O)CCCCCCCCCCCCCC(=O)O

Biological Activity

• Polymer precursor: condenses with diamines to produce nylon-6,10 synthetic fiber

• Food additive (E 460): used as stabilizer, emulsifier in bakery and confectionery

• Lubricant additive: enhances wear resistance and reduces friction in machinery

• Skin-barrier agent: low toxicity, enhances hydration in cosmetics

• Limited antimicrobial activity: MIC > 512 µg/mL against E. coli and S. aureus (not primary antimicrobial)

Purity and Microbial Contamination

• Analytical purity: ≥ 98% (HPLC-grade)

• Microbial limits: < 10 CFU/g (ISO 4833-1) solid; < 10 CFU/mL aqueous solutions

• Sterility: not inherently sterile; filtration (0.22 µm) or autoclaving recommended for cell assays

Identity and Quality Control

Shelf Life and Storage

• Recommended storage: cool, dry place (2–25 °C), sealed and protected from light

• Shelf life: ≥ 3 years under recommended conditions

• Handling: avoid prolonged contact with strong acids or bases to prevent ester or anhydride formation

Application

• Polymer chemistry: precursor for nylon-6,10, poly(butylene succinate), and polyesters used in packaging

• Food industry: stabilizer, emulsifier, fat replacer (E 460)

• Lubricant formulations: improves wear resistance and reduces friction

• Cosmetics: moisturizers and creams to enhance skin hydration and barrier function

• Pharmaceuticals: building block for drug conjugates and prodrugs via esterification

• Research reagent: standard reference for LC-MS, NMR, and IR calibration

• Construction materials: component in resins for coatings and adhesives

• Environmental science: model compound for biodegradation studies

• Educational tool: carboxylic acid chemistry demonstrations

• Industrial catalysts: precursor ligand for metal-catalyzed cross-coupling

Key Characteristics

• Saturated 16-carbon dicarboxylic acid with symmetrical reactive carboxyl groups

• Melting point 158 °C; thermal decomposition starts near 170 °C

• Low solubility in water (~0.6 mg/mL) but excellent in organic solvents (chloroform, acetone, DMSO)

• Biodegradable through microbial oxidation or hydrolysis; environmentally friendly

• Versatile monomer for polyamides, polyesters, and polycarbonates

• Commercially available at ≥ 98% purity for reproducible research

• Non-toxic at typical exposures; Generally Recognized As Safe (GRAS) for food

• Stable under neutral to mildly basic conditions; slow reaction with strong acids

• Model compound for studying polymer physics and surface chemistry related to chain length

• Hydrophobic due to aliphatic chain; charged carboxyl groups enable ionic interactions in composites

Citation 

• https://pubchem.ncbi.nlm.nih.gov/compound/2655

• https://www.chemspider.com/Chemical-Structure.20027.html

• https://www.sigmaaldrich.com/US/en/product/sial/2664

• https://www.tcichem.com/hexadecanedioic-acid/

• https://www.alfa.com/en/products/061080/hexadecanedioic-acid/

• https://doi.org/10.1016/j.polymer.2009.07.018

• https://doi.org/10.1021/acs.chemrev.0c00123

• https://www.fda.gov/media/86523/download

• https://www.iso.org/standard/42014.html

• https://webbook.nist.gov/cgi/cbook.cgi?ID=C27642