Palmitic acid
Palmitic acid is a 16-carbon saturated fatty acid, the most abundant saturated fat in the human body and a primary output of endogenous de novo lipid synthesis. It is found in significant concentrations in palm oil, tallow, dairy fat, and human sebum, and is produced internally whenever the body synthesises fatty acids from carbohydrate or protein substrates via fatty acid synthase (FASN). Its saturation – no double bonds across its 16-carbon chain – gives it a straight, rigid molecular geometry that packs tightly in lipid bilayers and resists oxidative degradation. In skin biology, palmitic acid’s significance extends well beyond its structural presence: it is the direct biochemical starting point for ceramide synthesis. [1]
Role in Ceramide Synthesis
Palmitoyl- CoA – the activated form of palmitic acid – is the direct substrate for serine palmitoyltransferase (SPT), the rate-limiting enzyme that initiates the de novo ceramide synthesis pathway. SPT condenses palmitoyl-CoA with serine to produce 3-ketosphingosine, the first committed step in sphingolipid biosynthesis. Every ceramide molecule produced via the de novo pathway begins with palmitic acid at this step. This makes palmitic acid availability a foundational variable in barrier lipid production – not in the sense that dietary supplementation improves ceramide output under normal conditions, but in the sense that anything impairing palmitoyl-CoA availability or SPT activity directly constrains ceramide synthesis capacity. The inflammatory suppression of SPT by IL-4 and IL-13, for example, reduces ceramide production precisely because it blocks this palmitic acid entry point. [1]
Oxidative Stability and Topical Relevance
With no double bonds available for oxidative attack, palmitic acid is among the most chemically stable of the common skin-relevant fatty acids. Formulations and oils with high saturated fatty acid content – tallow, shea butter, and coconut oil among them – resist the oxidative degradation that generates reactive aldehydes such as 4-hydroxynonenal (4-HNE) from polyunsaturated fatty acids (PUFAs). For topical applications where minimising oxidation products at the skin surface is a priority, the saturated fatty acid profile of palmitic acid-rich formulations represents a genuine compositional advantage over high-PUFA alternatives, independent of any claims about palmitic acid’s direct biological activity at the skin surface.
References
Mizutani Y, Sun H, Ohno Y, et al. (2013). Cooperative Synthesis of Ultra Long-Chain Fatty Acid and Ceramide during Keratinocyte Differentiation. PLoS One, 8(6), e67317 . doi.org/10.1371/journal.pone.0067317
Molecular Structure
- Formula
- C₁₆H₃₂O₂
- Weight
- 256.42 g/mol
- IUPAC
- hexadecanoate;hydron
Computational Identifiers
| InChI | InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) | |
|---|---|---|
| InChIKey | IPCSVZSSVZVIGE-UHFFFAOYSA-N | |
| Canonical SMILES | [H+].CCCCCCCCCCCCCCCC(=O)[O-] | |
Data sourced from: PubChem (NCBI) ↗ | ||
Also Known As
- hexadecanoic acid
Learn More
This topic is discussed in 1 article:
