Skip to the main content

Sebaleic acid

MolecularEntity Fatty Acid

Sebaleic acid is an 18-carbon with two double bonds at the delta-5 and delta-8 positions (C18:2 Δ5,8), produced in human by the elongation of (C16:1 Δ6) followed by further desaturation. Its name derives from the Latin – 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 including , lard, and dairy fat.

Sebaleic acid is part of the distinctively human sebaceous pathway – the sapienic acid cascade – which runs parallel to but distinct from the and pathways operating in other tissues. This pathway is initiated by FADS2 acting on to produce sapienic acid, then proceeds through elongation to sebaleic acid, making both molecules markers of active human 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 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.

Published
Updated

Molecular Structure

2D Molecular Structure of Sebaleic acid
Formula
C₁₈H₃₂O₂
Weight
280.40 g/mol
IUPAC
(5Z,8Z)-octadeca-5,8-dienoic acid
Computational Identifiers
Chemical 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-
InChIKeyUQQPKQIHIFHHKO-XVTLYKPTSA-N
Canonical SMILESCCCCCCCCCC=CCC=CCCCC(=O)O
Isomeric SMILESCCCCCCCCC/C=C\C/C=C\CCCC(=O)O
Data sourced from: PubChem (NCBI) ↗