Through histone deacetylase inhibition, pelargonic acid upregulates endogenous host defense peptides, improving the function of the intestinal epithelial immunological barrier [1].

Metabolism / Metabolites
Infusion of an emulsion containing 20% trinonyl nonanoate, 0.9% sodium chloride, and 1% soy lecithin into dogs resulted in the oxidation of nonanoate. Nonanoate was metabolized in the liver to produce ketone bodies. The metabolic pathway was β-oxidation, and no evidence of chain elongation or tissue storage of this acid was found in rats. Metabolism of the terminal propionic acid residues led to increased glucose and glycogen synthesis.

[1]. Caprylic acid and nonanoic acid upregulate endogenous host defense peptides to enhance intestinal epithelial immunological barrier function via histone deacetylase inhibition.Int Immunopharmacol. 2018 Dec;65:303-311.

Nonanoic acid is a C9 straight-chain saturated fatty acid naturally found in esters of geranium oil. It possesses antifungal properties and is also used as a herbicide, plasticizer, and raw material for varnish preparation. Nonanoic acid also acts as a feeding repellent, plant metabolite, flea metabolite, and algal metabolite. It is a straight-chain saturated fatty acid and a medium-chain fatty acid, the conjugate acid of nonanoic acid, derived from the hydrogenation of nonane. It has been reported to exist in tea trees, Artemisia species, and other organisms with relevant data. Atropine is a long-acting, selective, and reversible dihydrofolate reductase inhibitor, used as a broad-spectrum antibacterial agent in animals. Nonanoic acid is a naturally occurring nine-carbon saturated fatty acid. Ammonium nonanoate can be used as a herbicide. Its mechanism of action involves stripping the waxy cuticle of plants, leading to cell rupture, leakage, and ultimately death due to dehydration. Nonanoic acid is a metabolite of Saccharomyces cerevisiae.
See also: Fatty acids, C8-10 (note moved here).

---

Mechanism of Action
This study investigated the epidermal response to two different stimulants—nonanoic acid (NAA) and sodium dodecyl sulfate (SLS)—using two different methods. 80% NAA and 4% SLS solutions were applied to the skin under closed conditions for up to 24 hours. Elemental changes in frozen sections were determined by X-ray microanalysis. Compared to untreated skin, the sodium-potassium ratio in the skin significantly increased after 6 hours of NAA treatment, while it significantly decreased after 6 hours of SLS treatment. After 24 hours, both substances induced similar changes consistent with cellular damage. These results indicate that the responses of NAA and SLS are time-dependent. The mRNA expression levels of interleukin-1α (IL-1α), IL-1β (IL-1β), IL-6 (IL-6), IL-8 (IL-8), tumor necrosis factor-α (TNF-α), and granulocyte-macrophage colony-stimulating factor (GM-CSF) in biopsy tissues from stimulated and unstimulated skin were detected using reverse transcription polymerase chain reaction (RT-PCR) at 0, 4, 8, and 24 hours. The results showed that NAA (but not SLS) induced an increase in IL-6 mRNA expression. GM-CSF mRNA expression increased after SLS exposure, but not after NAA exposure. These results indicate that the upregulation of different cytokine mRNAs in the epidermis exhibits time- and substance-dependent differences within the first 24 hours of stimulant response. This may be due to the different effects of the stimulants on the cell membrane, a point also reflected by the differences in elemental content at 6 hours. Studies have shown that polyunsaturated fatty acids (such as arachidonic acid and docosahexaenoic acid), rather than monounsaturated fatty acids and saturated long-chain fatty acids, can promote basal neurite elongation and nerve growth factor (NGF)-induced neurite elongation in PC12 cells (a cell line derived from rat pheochromocytoma). On the other hand, short-chain fatty acids and valproic acid (2-propylvalerate) only enhance neurite growth in the presence of an inducer. In this study, researchers demonstrated that millimolecular concentrations of medium-chain fatty acids (MCFAs) can effectively induce neuronal differentiation in PC12 cells. Nonanoic acid, decanoic acid, and dodecanoic acid can also induce neurite growth, but their maximum effect is not as significant as that of caprylic acid.

C9H18O2

158.2380

158.131

112-05-0

Nonanoic acid-d17;130348-94-6;Nonanoic acid-d3;134646-27-8;Nonanoic acid-d4;1219795-27-3;Nonanoic acid-d2;62689-94-5

8158

Colorless to light yellow liquid

0.906 g/mL at 25 °C(lit.)

268-269 °C(lit.)

9 °C(lit.)

212 °F

<0.1 mm Hg ( 20 °C)

n20/D 1.432(lit.)

2.821

1

2

7

11

99.7

0

O([H])C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O

FBUKVWPVBMHYJY-UHFFFAOYSA-N

InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)

nonanoic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 100 mg/mL (~631.95 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (15.80 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

---

Solubility in Formulation 2: ≥ 2.5 mg/mL (15.80 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

---

View More

Solubility in Formulation 3: ≥ 2.5 mg/mL (15.80 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

---

 (Please use freshly prepared in vivo formulations for optimal results.)