Sebaleic acid
Sebaleic acid is an 18-carbon polyunsaturated fatty acid with two double bonds at the delta-5 and delta-8 positions (C18:2 Δ5,8), produced in human sebocytes by the elongation of sapienic acid (C16:1 Δ6) followed by further desaturation. Its name derives from the Latin sebum – the same root as sebaceous, sebocyte, and seborrhoea – reflecting that it was identified as a product specific to sebaceous secretion. Like sapienic acid, sebaleic acid is produced by no other known mammalian species and is absent from all plant-derived oils and animal fats including tallow, lard, and dairy fat.
Sebaleic acid is part of the distinctively human sebaceous fatty acid pathway – the sapienic acid cascade – which runs parallel to but distinct from the linoleic acid and arachidonic acid pathways operating in other tissues. This pathway is initiated by FADS2 acting on palmitic acid to produce sapienic acid, then proceeds through elongation to sebaleic acid, making both molecules markers of active human sebaceous gland function rather than dietary fatty acid incorporation.
Its biological roles in the sebum film are not yet as well characterised as those of sapienic acid, but sebaleic acid contributes to the antimicrobial chemical environment of the skin surface alongside its precursor. Its double bond geometry, at delta-5 and delta-8 rather than the more common delta-9 or delta-6 positions found in dietary fatty acids, is structurally unusual and may contribute to the distinctive physical properties of human sebum as a surface lipid. The significance of sebaleic acid for skincare science is definitional: its complete absence from every non-human fat source is further evidence that sebum mimicry claims for any topical fat require careful qualification.
Molecular Structure
- Formula
- C₁₈H₃₂O₂
- Weight
- 280.40 g/mol
- IUPAC
- (5Z,8Z)-octadeca-5,8-dienoic acid
Computational Identifiers
| InChI | InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h10-11,13-14H,2-9,12,15-17H2,1H3,(H,19,20)/b11-10-,14-13- | |
|---|---|---|
| InChIKey | UQQPKQIHIFHHKO-XVTLYKPTSA-N | |
| Canonical SMILES | CCCCCCCCCC=CCC=CCCCC(=O)O | |
| Isomeric SMILES | CCCCCCCCC/C=C\C/C=C\CCCC(=O)O | |
Data sourced from: PubChem (NCBI) ↗ | ||