1,20-icosanedioic acid

1,20-Icosanedioic acid is a long-chain saturated dicarboxylic acid with a 20-carbon alkane backbone and carboxylic acid groups at both ends. It exhibits amphiphilic properties due to its hydrophobic alkyl chain and hydrophilic carboxyl termini. Although relatively rare in nature, it can be extracted in small amounts from plant waxes and microbial lipids or more commonly synthesized chemically, often by oxidation of long-chain diols. This compound serves as a valuable building block in polymer chemistry, organic synthesis, and potentially biological contexts where its length and amphiphilicity influence membrane interactions and drug delivery. Its two carboxyl groups facilitate diverse chemical modifications.

Appearance

• White to off-white crystalline solid or powder

Source

• Naturally isolated from plant waxes or microbial lipids in small quantities

• More commonly produced via chemical synthesis (oxidation of long-chain diols or similar methods)

Molecular Weight and Structure

• Molecular Weight: 342.56 g/mol

• Structure: HOOC-(CH₂)₁₈-COOH (20-carbon dicarboxylic acid, saturated alkane chain)

Biological Activity

• Generally limited direct biological activity

• Acts as precursor for biologically active derivatives via chemical modifications

• Long-chain fatty acid properties can influence membrane behavior or lipid metabolism in relevant contexts

• Derivatives with added functional groups may exhibit targeted biological activity

Purity and Microbial Contamination

Identity and Quality Control

Shelf Life and Storage

Application

• Polymer Chemistry: monomer or co-monomer in polyesters, polyamides, and polymers modifying melting point, flexibility, hydrophobicity

• Lubricants and Greases: additive to improve lubricity and stability

• Cosmetics: emollient, thickener, or film former in formulations

• Surfactants: precursor for surfactant synthesis

• Chemical Intermediate: platform for synthesis of diesters, diamides, and other functional molecules

• Drug Delivery: potential in liposomes, nanoparticles due to amphiphilicity

Key Characteristics

• Long-chain saturated dicarboxylic acid

• Amphiphilic: hydrophobic alkane chain, hydrophilic carboxylic acid ends

• High melting point due to chain length

• Versatile chemical building block with wide application potential

Citation

• https://www.researchgate.net/publication/322343441_Synthesis_and_Characterization_of_Novel_Polyamides_Based_on_Dicarboxylic_Acids_and_Diamines_Containing_Triazole_Rings

• https://patents.google.com/patent/US6569378B1/en

• https://www.tandfonline.com/doi/abs/10.1080/00914037.2013.815632

• https://www.sciencedirect.com/science/article/abs/pii/0032386196001750

• https://pubs.acs.org/doi/abs/10.1021/ma00157a011

• https://link.springer.com/article/10.1007/BF00652565

• https://www.jstage.jst.go.jp/article/gomu/78/4/78_169/_article

• https://www.sciencedirect.com/science/article/pii/S003239500700570X

• https://pubs.rsc.org/en/content/articlelanding/2016/ra/c6ra05530e

• https://www.google.com/patents/WO2014184262A1?cl=en