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% TRINONANOATE, 0.9% SODIUM CHLORIDE, & 1% SOYBEAN LECITHINS INTO DOGS RESULTED IN OXIDN OF NONANOIC ACID.
NONANOIC ACID IS METABOLIZED BY THE LIVER TO PRODUCE KETONE BODIES. METABOLISM OCCURS VIA BETA-OXIDATION, AND NO EVIDENCE WAS FOUND IN RATS OF CHAIN ELONGATION OR TISSUE STORAGE OF THE ACID. METAB OF THE TERMINAL PROPIONIC ACID RESIDUE RESULTS IN 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 which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers. It has a role as an antifeedant, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a straight-chain saturated fatty acid and a medium-chain fatty acid. It is a conjugate acid of a nonanoate. It derives from a hydride of a nonane.
Nonanoic acid has been reported in Camellia sinensis, Artemisia xerophytica, and other organisms with data available.
Aditoprim is a long-acting, selective, reversible inhibitor of dihydrofolate reductase with application as a broad-spectrum antibacterial agent in animals.
Nonanoic Acid is a naturally-occurring saturated fatty acid with nine carbon atoms. The ammonium salt form of nonanoic acid is used as an herbicide. It works by stripping the waxy cuticle of the plant, causing cell disruption, cell leakage, and death by desiccation.
Nonanoic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
See also: Fatty acids, C8-10 (annotation moved to).

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Mechanism of Action
The epidermal response to 2 different irritants, nonanoic acid (NAA) and sodium lauryl sulfate (SLS), was investigated with 2 different methods. NAA 80% and SLS 4% were applied under occlusion for up to 24 hr. Elemental changes were determined in cryosections by x-ray microanalysis. Compared to unexposed skin a significantly higher sodium/potassium ratio was found after 6 hr in NAA-exposed skin and a lower ratio in SLS-exposed. At 24 hr both substances had induced similar changes, compatible with a cell injury. The findings demonstrate a time-dependent NAA and SLS response. With reverse transcription polymerase chain reaction, the mRNA expression of interleukin-1 alpha (IL-1 alpha), -1 beta (IL-1 beta), -6 (IL-6), and -8 (IL-8), tumor necrosis factor alpha (TNF alpha) and granulocyte macrophage colony stimulating factor (GM-CSF) in shave biopsies from irritated and unexposed skin was studied at 0, 4, 8, and 24 hr. NAA, but not SLS, induced an increase in mRNA expression for IL-6. mRNA-expression for GM-CSF was increased after SLS exposure, but not after NAA. These findings indicate a time and substance dependent difference in the up-regulation of mRNA for different cytokines in epidermis during the first 24 hr of the irritants' reaction. This might be the effect of differences in the irritants action on the cell membranes, which is also reflected by the differences found in the elemental content at 6 hr.
It has been shown that polyunsaturated fatty acids such as arachidonic and docosahexanoic acids but not monounsaturated and saturated long-chain fatty acids promote basal and nerve growth factor (NGF)-induced neurite extension of PC12 cells, a line derived from a rat pheochromocytoma. On the other hand, short-chain fatty acids and valproic acid (2-propylpentanoic acid) enhance the growth of neurite processes of the cells only in the presence of inducers. In this study, /investigators/ demonstrated that straight medium-chain fatty acids (MCFAs) at millimolar concentrations alone potently induced neuronal differentiation of PC12 cells. ... Nonanoic, decanoic, and dodecanoic acids also induced growth of neurite processes, but their maximal effects were less marked than that of octanoic 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.

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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.

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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.

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