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Pentadecanoic acid

Name: Pentadecanoic acid
SKU: ACMA00045784
Rating: 5 (1 reviews)

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Catalog NumberACMA00045784

CAS Number1002-84-2

CategoryFatty Acids and Ester Homologs

Description

OtherSolid;Solid;Solid

Synonyms

Pentadecylic acid

IUPAC Name

pentadecanoic acid

Molecular Weight

242.40

Molecular Formula

C15H30O2

InChI

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)

InChI Key

WQEPLUUGTLDZJY-UHFFFAOYSA-N

Boiling Point

257 °C

Melting Point

51-53 °C (lit.)

Purity

98%

Appearance

Solid

Application

Pentadecanoic acid is a saturated fatty acid that plays a crucial role as a biomarker for assessing milk fat intake and its associated metabolic risks. Rarely found in nature, it is primarily sourced from cow's milk fat and can also be detected in hydrogenated mutton fat. This fifteen-carbon fatty acid, although present in low concentrations in human plasma, has become increasingly significant in research as a quantitative internal standard and as a biomarker for dietary food intake assessment. Recent studies have highlighted its potential as a biomarker for coronary heart disease (CHD) and type II diabetes mellitus (T2D) risk, owing to its inverse association with CHD incidence. Beyond dietary and metabolic research, pentadecanoic acid also exhibits biological activity, with potential anxiolytic, antinociceptive, and antimicrobial properties, showing its global relevance in both nutritional science and pharmacology.

Storage

Room temperature

C No.Chain

C15:0

Compound Derivative

Acid

Exact Mass

242.22458g/mol

Fatty Acid

Pentadecanoic

Physical State

Solid

Subcategory

Saturated

Download COA Download MSDS

Case Study

Pentadecanoic Acid for the Prevention of Candida albicans-Klebsiella pneumoniae Polymicrobial Biofilm Formation on Medical Device Surfaces

Galdiero, E., Ricciardelli, A., D'Angelo, C., De Alteriis, E., Maione, A., Albarano, L., ... & Parrilli, E. (2021). Research in microbiology, 172(7-8), 103880.

Pentadecanoic acid, a saturated long-chain fatty acid, has emerged as a promising biofilm-inhibiting agent with potential applications in medical device protection. Biofilm formation, particularly in mixed-species communities such as Candida albicans and Klebsiella pneumoniae, poses a significant challenge due to its inherent resistance to conventional antimicrobial therapies.
Recent studies have demonstrated pentadecanoic acid's dual capacity to prevent biofilm establishment and to destabilize preformed biofilm matrices in polymicrobial systems. Structurally similar to diffusible signal factors (DSFs) and leveraging the known anti-biofilm activity of fatty acids, pentadecanoic acid disrupts microbial adherence and biofilm architecture, exhibiting a stronger inhibitory effect against bacterial cells within the consortium.
A practical application was achieved by adsorbing pentadecanoic acid onto polydimethylsiloxane (PDMS) surfaces, creating an anti-biofilm coating. Under dynamic flow conditions, this functionalized surface effectively suppressed the development of mixed C. albicans-K. pneumoniae biofilms, as confirmed via confocal laser scanning microscopy. Gene expression analysis indicated downregulation of key biofilm-associated genes, offering mechanistic insights into the compound's mode of action.
Given its efficacy against other pathogens, including Staphylococcus epidermidis and Xanthomonas campestris, pentadecanoic acid coatings present a viable preventive strategy for reducing polymicrobial infections on indwelling medical devices. Future research aims to enhance its synergistic performance with conventional antifungal agents, potentially lowering dosage requirements and minimizing drug toxicity while maintaining robust anti-biofilm protection.

Pentadecanoic Acid as a Precursor for the Stereoselective Biosynthesis of ω-1 Hydroxylated Fatty Acids via Cytochrome P450BM-3

Schneider, Silke, et al. Tetrahedron: Asymmetry 9.16 (1998): 2832-2844.

Pentadecanoic acid, a saturated C15 fatty acid, serves as an efficient substrate for the stereoselective biosynthesis of hydroxylated derivatives with high industrial and pharmaceutical relevance. In a biotransformation process utilizing recombinant Escherichia coli K27 (pCYP102, pGEc47) expressing cytochrome P450BM-3 monooxygenase [EC 1.14.14.1], pentadecanoic acid was converted into 12-, 13-, and 14-hydroxypentadecanoic acids.
The reaction was conducted under oxygen-limited conditions (5% dissolved oxygen tension) to minimize over-oxidation, with a 6-hour conversion period in a 3 L bioreactor containing M9 minimal medium. Post-reaction, the culture supernatants underwent filtration, hexane extraction, and methylation to produce the corresponding methyl esters. Purification via reversed-phase HPLC enabled separation of the regioisomers, which were subsequently crystallized at controlled temperatures.
Notably, chiral HPLC revealed that the ω-1 hydroxylated product, 14-hydroxypentadecanoic acid methyl ester, was obtained in optically pure (S)-(+)-form with an enantiomeric excess exceeding 95%, highlighting the enzyme's exceptional stereoselectivity. This aligns with prior findings that P450BM-3 catalysis offers high regio- and enantioselective oxidation of long-chain fatty acids.
These hydroxylated derivatives, particularly optically pure 14-hydroxypentadecanoic acid, hold potential as chiral building blocks in fine chemical synthesis, biodegradable surfactants, and specialty lubricants. This case demonstrates the value of pentadecanoic acid as a renewable feedstock for precision biocatalysis, enabling sustainable production of enantiomerically enriched ω-hydroxy fatty acids.

Pentadecanoic Acid Enhances Glucose Uptake and GLUT4 Translocation in C2C12 Myotubes

Fu, Wen-Cheng, et al. Food & nutrition research 65 (2021): 10-29219.

Pentadecanoic acid (PA), a saturated odd-chain fatty acid naturally found in dairy fat and certain plant sources, has attracted attention for its potential metabolic benefits. Recent in vitro studies using differentiated C2C12 myotubes demonstrated that PA can significantly enhance glucose metabolism without inducing cytotoxic effects at concentrations below 40 μM.
Cell viability assays (MTT) confirmed that treatment with 5-40 μM PA for 48 hours did not compromise myotube viability. Functional assays revealed that PA promoted glucose consumption in a time-dependent manner, with 40 μM treatment for 12, 24, and 48 hours resulting in statistically significant increases compared to controls (P < 0.01). Complementary 2-NBDG uptake assays showed that 20 μM and 40 μM PA enhanced glucose uptake by 35.1% and 43.8%, respectively (P < 0.05).
Mechanistic analysis indicated that this effect was accompanied by increased translocation of glucose transporter type 4 (GLUT4) to the plasma membrane, suggesting that PA facilitates glucose entry into skeletal muscle cells through insulin-independent pathways. This property positions pentadecanoic acid as a potential nutraceutical candidate for improving peripheral glucose utilization and supporting metabolic health.
These findings highlight the physiological relevance of odd-chain fatty acids such as pentadecanoic acid in modulating glucose homeostasis. Further research is warranted to explore its signaling mechanisms and potential therapeutic role in insulin resistance and type 2 diabetes management.

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