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Pentadecylic Acid is a saturated fatty acid with the chemical formula C₁₅H₃₀O₂ and a straight-chain structure containing 15 carbon atoms.
Pentadecylic Acid is classified as an odd-chain fatty acid, which distinguishes it from the more common even-chain fatty acids found in nature.
Pentadecylic acid is also known by its systematic name pentadecanoic acid.
CAS Number: 1002-84-2
Molecular Formula: C15H30O2
Molecular Weight: 242.4
EINECS Number: 213-693-1
Synonyms:PENTADECANOIC ACID, 1002-84-2, Pentadecylic acid, n-Pentadecanoic acid, C15:0, CCW02D961F, DTXSID2021652, NSC-28486, DTXCID601652, FEMA No. 4334, CHEBI:42504, NSC28486, fatty acid 15:0, RefChem:171339, 213-693-1, Pentadecyclic acid, n-Pentadecylic acid, MFCD00002745, 2,2-Dideuteropentadecanoic acid, Pentadecanoic acid, 99%, 64118-45-2, CHEMBL460025, NSC 28486, F15, EINECS 213-693-1, BRN 1773831, UNII-CCW02D961F, Pentadecyclate, n-Pentadecylate, AI3-36441, n-Pentadecanoate, pentadecansäure, PENTADECANOICACID, tetradecylcarboxylic acid, tetradecyl carboxylic acid, bmse000558, SCHEMBL6311, Pentadecanoic acid, ≥99%, 4-02-00-01147 (Beilstein Handbook Reference), WLN: QV14, SCHEMBL147618, SCHEMBL251103, SCHEMBL421576, orb1299267, orb3025213, SCHEMBL1275174, SCHEMBL6797697, FA 15:0a, SCHEMBL10611067, MSK1713, PENTADECANOIC ACID [FHFI], HMS5085I12, Tox21_201197, BDBM50242348, LMFA01010015, s6234, STL453783, AKOS015903762, CS-W004283, EBC-612280, FA 15:0, HY-W004283, Pentadecanoic acid, analytical standard, NCGC00248954-01, NCGC00258749-01, AS-57005, BP-27916, SY009985, CAS-1002-84-2, Pentadecanoic acid, ~99% (capillary GC), DB-343938, NS00015703, P0035, ST51037413, EN300-176407, H10804, 9B1C70C0-EF6E-4FCF-A3D3-DACCDCCF791C, F321973, Q418951, 1-PENTADECANOIC ACID;RARECHEM AL BO 0368;TETRADECANE-1-CARBOXYLIC ACID;PENTADECYCLIC ACID;PENTADECYLIC ACID;PENTADECANOIC ACID;N-PENTADECYLIC ACID;N-PENTADECANOIC ACID
Pentadecylic acid occurs naturally in small amounts in dairy fat, ruminant milk, butter, and certain animal fats.
Pentadecylic Acid is produced in ruminants through microbial fermentation processes in the rumen.
Because humans do not synthesize odd-chain fatty acids efficiently, its presence in the body is largely diet-derived.
Physically, pentadecylic acid is a white to off-white crystalline solid at room temperature.
Pentadecylic Acid has a relatively high melting point compared to shorter fatty acids due to increased van der Waals interactions along the hydrocarbon chain.
Its solubility in water is extremely low, while it is soluble in nonpolar organic solvents such as chloroform and hexane.
Pentadecylic Acid behaves like other saturated fatty acids.
Pentadecylic Acid undergoes typical carboxylic acid reactions such as esterification, salt formation, and reduction.
The absence of double bonds makes it resistant to oxidative degradation compared to unsaturated fatty acids.
Pentadecylic acid is of interest in nutritional, biomedical, and analytical research.
Pentadecylic Acid is often used as a biomarker for dairy fat intake in dietary studies.
Its odd-chain nature also makes it useful in lipid metabolism and epidemiological research.
Pentadecylic Acid is a straight-chain saturated fatty acid containing fifteen-carbon atoms.
It has a role as a plant metabolite, a food component, a Daphnia magna metabolite, a human blood serum metabolite and an algal metabolite.
Pentadecylic Acid is a long-chain fatty acid and a straight-chain saturated fatty acid.
Pentadecylic Acid is a conjugate acid of a pentadecanoate.
Pentadecylic acid is part of the group of odd-chain saturated fatty acids, which have gained attention in recent years for their potential health relevance.
Unlike even-chain fatty acids, odd-chain fatty acids are not efficiently synthesized by human fatty acid synthase.
As a result, circulating levels of pentadecylic acid are strongly influenced by dietary intake, particularly from dairy products.
In biological systems, pentadecylic acid can be incorporated into triglycerides, phospholipids, and cholesteryl esters.
Although present at low concentrations, it contributes to overall lipid composition.
Its metabolism involves β-oxidation pathways that ultimately yield propionyl-CoA rather than acetyl-CoA.
Pentadecylic acid has been studied in epidemiological research as an indicator of metabolic health.
Higher circulating levels have been associated in some studies with reduced risk of type 2 diabetes and cardiovascular disease.
These associations are thought to reflect dietary patterns rather than direct biological activity.
In analytical chemistry, pentadecylic acid is commonly used as an internal standard.
Its odd-chain length allows it to be easily distinguished from endogenous even-chain fatty acids in chromatographic analysis.
This makes it valuable in gas chromatography and mass spectrometry of lipid samples.
From a physicochemical perspective, pentadecylic acid exhibits well-defined crystalline behavior.
Its melting and solidification properties follow predictable trends based on chain length.
These characteristics are useful for studying structure–property relationships in fatty acids.
Pentadecylic acid is chemically stable under normal conditions due to its saturated structure.
Pentadecylic Acid is less prone to oxidation compared to polyunsaturated fatty acids.
This stability supports its use in long-term storage and analytical reference materials.
Melting point: 51–53 °C (lit.)
Boiling point: 257 °C at 100 mm Hg (lit.)
Density: 0.8423
Refractive index: 1.4292
FEMA: 4334 (PENTADECANOIC ACID)
Flash point: >230 °F
Storage temperature: Store below +30 °C
Solubility: Soluble in ethanol
Form: Powder or flakes
pKa: 4.78 ± 0.10 (predicted)
Color: White
Odor: Waxy
Biological source: Synthetic (organic)
Water solubility: 12 mg/L (20 °C)
JECFA number: 2300
BRN: 1773831
Stability: Stable; combustible; incompatible with bases, reducing agents, and oxidizing agents
InChI: 1S/C₁₅H₃₀O₂/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17/h2-14H₂,1H₃,(H,16,17)
InChIKey: WQEPLUUGTLDZJY-UHFFFAOYSA-N
SMILES: CCCCCCCCCCCCCCC(O)=O
LogP: 6.62
Pentadecylic Acid, which originate from rumen microbial fermentation, is a kind of minor saturated fatty acid (FAs) in ruminant fat.
Its concentration in conventionally produced cow milk is on average 1.2% of total FAs, respectively. Concentrations in organically produced milk are somewhat higher.
Pentadecylic acid is also referred to as C15:0, reflecting its carbon chain length and lack of double bonds.
This notation is commonly used in lipid science and nutrition to classify fatty acids.
Its odd-numbered chain length makes it less abundant in nature compared to even-chain saturated fatty acids.
In microbial systems, pentadecylic acid can be synthesized by certain bacteria through alternative fatty acid biosynthesis pathways.
These microbial sources contribute indirectly to its presence in ruminant-derived foods.
This microbial origin further supports its use as a dietary biomarker.
Pentadecylic acid shows distinct chromatographic behavior due to its chain length.
Pentadecylic Acid elutes between myristic acid (C14:0) and palmitic acid (C16:0) in gas chromatography.
This predictable position is useful for lipid profiling and quality control.
In lipidomics and metabolomics, pentadecylic acid is used to study fatty acid turnover and dietary fat assimilation.
Its minimal endogenous synthesis allows clearer interpretation of intake-related changes.
This makes it valuable in nutritional intervention and population studies.
From a materials perspective, pentadecylic acid contributes to the physical properties of fats and lipid mixtures.
It influences melting behavior and crystal packing when present alongside other saturated fatty acids.
These effects are relevant in food science, particularly in dairy fat texture and stability.
Pentadecylic acid is not considered an essential fatty acid.
However, its presence provides insight into metabolic pathways involving propionate metabolism.
This links it indirectly to gut microbiota activity and metabolic health research.
Pentadecylic Acid is valued more for its diagnostic and analytical significance than for direct functional use.
Its odd-chain structure provides unique information in nutritional, biochemical, and epidemiological studies.
This distinguishes it from more common saturated fatty acids used primarily for energy storage.
Pentadecylic acid has a linear, unbranched alkyl chain that allows tight molecular packing in the solid state.
This packing results in a relatively sharp melting transition compared to shorter fatty acids.
Such behavior is often used to study phase transitions and crystallization in lipid systems.
In food science, pentadecylic acid contributes subtly to the physical characteristics of dairy fats.
Although present in small quantities, it participates in mixed-crystal formation with other saturated fatty acids.
This can influence firmness, spreadability, and thermal behavior of butter and milk fat.
Pentadecylic acid is increasingly used as a nutritional biomarker in population studies.
Because humans synthesize very little C15:0 endogenously, blood and tissue levels reflect long-term intake of dairy fat.
This makes it useful for objective dietary assessment compared to self-reported intake data.
In metabolic research, pentadecylic acid provides insight into odd-chain fatty acid metabolism.
Its β-oxidation generates propionyl-CoA, which enters metabolic pathways distinct from acetyl-CoA.
This links pentadecylic acid indirectly to vitamin B₁₂–dependent metabolism and gut microbial activity.
Pentadecylic acid is also used in calibration mixtures for lipid standards.
Its odd-chain length ensures clear separation from endogenous fatty acids during analysis.
This improves accuracy in quantitative lipidomics and fatty acid profiling.
From a toxicological standpoint, pentadecylic acid is considered biologically inert at normal exposure levels.
Pentadecylic Acid does not exhibit pro-oxidant behavior or membrane toxicity typical of some long-chain fatty acids.
This benign profile supports its widespread use in research and analytical applications.
Uses Of Pentadecylic Acid:
Pentadecanoic acid is a saturated fatty acid. Pentadecanoic acid was utilized as a biomarker to examine for the intake of milk fat in relation to its metabolic risk factors.
Pentadecanoic Acid that is also produced by certain plant species and acts as a toxic essential oil, which is known to exhibits potential anxiolytic, antinociceptive and antimicrobial properties.
Pentadecylic acid is widely used as a biomarker of dairy fat intake in nutritional and epidemiological studies.
Because humans synthesize very little C15:0 endogenously, its presence in blood or tissues reflects consumption of ruminant-derived foods.
This makes it valuable for objective dietary assessment and metabolic health research.
In analytical chemistry, pentadecylic acid is commonly used as an internal standard in lipid analysis.
Its odd-chain structure allows clear differentiation from naturally abundant even-chain fatty acids.
This improves accuracy in gas chromatography and mass spectrometry measurements.
Pentadecylic acid is used in lipid metabolism and lipidomics research.
It helps study odd-chain fatty acid oxidation and propionyl-CoA–related metabolic pathways.
These studies are important for understanding gut microbiota contributions and metabolic regulation.
In food science, pentadecylic acid contributes to the characterization of dairy fat composition.
It is used to authenticate milk fat and detect adulteration with non-dairy fats.
This supports quality control and food authenticity testing.
Pentadecylic acid is also applied in calibration mixtures and reference materials.
Its predictable chromatographic behavior makes it suitable for method validation.
This use is common in laboratories studying fatty acids, nutrition, and biochemistry.
Pentadecylic acid is used in clinical and population-based studies to investigate links between dairy fat intake and cardiometabolic health.
Measured circulating levels of C15:0 are correlated with long-term dietary patterns rather than short-term intake.
This supports its use in large-scale nutritional epidemiology.
In metabolomics research, pentadecylic acid is included in targeted lipid panels.
Its odd-chain nature allows researchers to track specific metabolic fluxes distinct from even-chain fatty acids.
This helps clarify fatty acid synthesis, degradation, and transport pathways.
Pentadecylic acid is applied in food authentication and fraud detection.
The ratio of C15:0 to other fatty acids can indicate whether dairy products have been diluted or replaced with vegetable fats.
This application is important for regulatory compliance and consumer protection.
In microbial and rumen biology research, pentadecylic acid is used to study microbial fatty acid synthesis.
It serves as an indicator of bacterial lipid contribution in ruminant systems.
These studies help explain how diet and microbiota influence milk fat composition.
Pentadecylic acid is also used in method development for lipid extraction and derivatization.
It helps optimize protocols for recovery and quantification of fatty acids.
This ensures reproducibility and accuracy in lipid analysis laboratories.
Safety Profile Of Pentadecylic Acid:
Poison by intravenous route when heated to decomposition it emits acrid smoke and irritating fumes.
Pentadecylic acid is considered to have low acute toxicity and is not classified as hazardous under normal laboratory or dietary exposure conditions.
It is a naturally occurring fatty acid present in common foods such as dairy products.
No significant toxic effects are expected from incidental exposure.
Skin and eye contact with solid pentadecylic acid may cause mild mechanical irritation.
This is mainly due to its waxy, crystalline nature rather than chemical reactivity.
Washing with water is generally sufficient to relieve any discomfort.
Inhalation risk is minimal because pentadecylic acid has negligible vapor pressure.
However, inhalation of fine dust during handling of powdered material may irritate the respiratory tract.
Good laboratory ventilation and dust control are recommended.
Pentadecylic acid is combustible at high temperatures.
If involved in a fire, it may decompose and release irritating fumes such as carbon monoxide and carbon dioxide.
Standard fire safety procedures for organic solids should be followed.
From an environmental perspective, pentadecylic acid is not considered ecotoxic.
Pentadecylic Acid is biodegradable and does not persist or bioaccumulate significantly in ecosystems.
Routine disposal as non-hazardous organic waste is generally appropriate.
