Nonanal targets various biological systems depending on the context. As a metabolite, it is involved in cancer metabolism and has been found in both human and plant metabolism. It acts as a growth factor for wood-rotting fungi and as an attractant for the pine shoot beetle. Its antidiarrheal activity suggests potential interactions with gastrointestinal targets.

Nonanal exhibits noteworthy efficacy against both B. cereus and L. monocytogenes, as evidenced by its respective MIC values of 7.8 μg/ml[1].

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In vitro studies demonstrate that nonanal shows significant activity against B. cereus and L. monocytogenes, with MIC values of 7.8 μg/ml for both pathogens. This antibacterial activity suggests potential applications as an antimicrobial agent. The compound's activity as a growth factor for wood-rotting fungi has also been characterized in vitro.

In mice that have castor oil-induced diarrhea, nonanal exhibits a strong inhibitory effect[1].

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In vivo activity data for nonanal are limited. The compound has been observed as a metabolite in human metabolism following ozone exposure. Its antidiarrheal activity has been reported, suggesting potential in vivo effects on gastrointestinal function. However, comprehensive in vivo pharmacological studies have not been extensively reported in the literature.

Non-cellular assays for nonanal typically involve antimicrobial susceptibility testing using broth microdilution or agar diffusion methods. MIC values are determined by incubating the compound with bacterial cultures and measuring growth inhibition. The compound's activity as a fungal growth factor is assessed by measuring fungal growth in the presence of varying concentrations of nonanal. Its role as a metabolite is characterized using analytical techniques such as GC-MS.

Cellular assays for nonanal have focused on its antimicrobial activity. Bacterial cultures of B. cereus and L. monocytogenes are treated with nonanal at various concentrations, and bacterial growth is monitored by measuring optical density or colony forming units. The compound's effects on mammalian cells have not been extensively characterized.

In vivo animal experiments for nonanal are limited. The compound has been studied as a metabolite in human exposure studies, particularly in relation to ozone exposure. Its antidiarrheal activity suggests it may have been tested in animal models of diarrhea, but specific experimental protocols are not well-documented in the available literature.

Metabolism / Metabolites
The specific activities of aldehyde dehydrogenase (ALDH) were determined in crude homogenate, mitochondrial supernatant, cytoplasmic, and microsomal fractions of rainbow trout (Oncorhynchus mykiss) liver using a variety of endogenous and exogenous aldehydes, as well as NAD+ and NADP+ as cofactors. All activities observed in the crude homogenate could be explained by the sum of cytoplasmic and microsomal activities. Among all fractions, the medium-chain substrates hexanal and nonanal exhibited the highest activities. β-Unsaturated aldehydes, such as (E,E)-2,4-nonadienal-1-aldehyde and trans,trans-2,4-decadienal, were good substrates for both fractions, while hydroxylated β-unsaturated trans-4-hydroxy-2-nonenal was only a good substrate for the microsomal fraction. Short-chain and aromatic exogenous substrates were metabolized at much lower rates; only the microsomal fraction was effective for acetaldehyde, acrolein, and benzaldehyde. Neither component can metabolize 2,5-dihydroxybenzaldehyde. NAD+ is the preferred cofactor for most substrates. The apparent affinity (Km) of hexanal and nonanal in the cytoplasmic component is comparable to that in rats, but the theoretical maximum reaction rate (Vmax) for these substrates and the specific activity of other substrates are much lower than those in mammals. Biochemical results indicate that trout are good at detoxifying endogenous lipid peroxidation products, but poor at detoxifying heterologous aldehydes. Uremic toxins often accumulate in the blood due to overeating or poor kidney filtration. Most uremic toxins are metabolic waste products and are usually excreted in urine or feces.

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Pharmacokinetic properties of nonanal are not well-characterized. As a volatile aldehyde, it may be absorbed through inhalation or ingestion and metabolized to nonanoic acid. It has been detected as a metabolite in humans following ozone exposure. The compound's stability and solubility in various media have not been extensively reported in the literature.

Toxicity Summary
Identification and Uses: Nonanal is a colorless liquid. It is not currently registered for use in the United States, but approved pesticide uses may change periodically, so it is essential to consult federal, state, and local authorities for currently approved uses. It is used in the perfume industry and as a flavoring agent. Human Exposure and Toxicity: Ozone exposure causes a significant early increase in nonanal levels in the lining fluid of the human respiratory tract. Nonanal levels return to baseline within 18 hours post-exposure. Nonanal produced in vitro via ozonoliposomes induces hemolysis in human erythrocytes; the combination of nonanal with H₂O₂ is significantly more potent than nonanal alone. Nonanal is negative in unplanned DNA synthesis assays on adult hepatocytes in the 3–100 mM concentration range. Animal Studies: A single transdermal administration of 5 g/kg nonanal to 3 rabbits with intact skin and 3 rabbits with abrasions resulted in the death of one rabbit and severe edema and burns at the administration site. Administering nonanoic acid (a metabolite of nonanal) to pregnant female rats at a dose of 1500 mg/kg body weight/day during days 6-15 of gestation did not reveal embryotoxicity, fetal toxicity, or teratogenicity. Nonanoic acid at concentrations of 0.1-100 μM induced sister chromatid exchange in rat hepatocytes and at concentrations of 3-100 mM induced unplanned DNA synthesis in adult rat hepatocytes. Nonanoic acid at concentrations of 0.1-0.3 mM induced positive mutations in V79 Chinese hamster lung cells and was negative in the modified Ames test (pre-incubation method) with Salmonella Typhimurium strains TA98, TA100, and TA1535 at concentrations of 1-666 μg/plate. Nonanoic acid was also negative in the Ames test with Salmonella Typhimurium strains TA102 and TA104 at concentrations up to 1 mg/plate. Chromosomal aberration assays were performed using rat hepatocytes at a concentration of 0.4 μg/mL. Uremic toxins (such as nonanal) are actively transported to the kidneys via organic ion transporters, particularly OAT3. Elevated uremic toxin levels can stimulate the production of reactive oxygen species (ROS). This appears to be mediated by the direct binding of uremic toxins to or inhibition of NADPH oxidases, particularly NOX4, which is abundant in the kidneys and heart (A7868). ROS can induce a variety of different DNA methyltransferases (DNMTs) involved in the silencing of a protein called KLOTHO. KLOTHO has been shown to play an important role in anti-aging, mineral metabolism, and vitamin D metabolism. Multiple studies have shown that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney disease due to elevated local ROS levels (A7869).

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Toxicity Data
LC (Rats)> 9,500 mg/m³/4h

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Non-human Toxicity Values
LD50 Rats Oral > 5,000 mL/kg Body Weight / From Table /
LD50 Rabbit Skin > 5,000 mL/kg Body Weight / From Table /
LC50 Rats Inhalation > 0.46 mg/L but < 3.8 mg/L/4 hours / Nonanoic acid, 97% /

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Toxicological data for nonanal are limited. Ozone exposure has been shown to result in a significant early increase in nonanal levels, suggesting that it may be a biomarker of oxidative stress. As a saturated fatty aldehyde, it may be metabolized to nonanoic acid, which is generally considered to have low toxicity. Standard laboratory safety precautions should be followed when handling the compound.

[1]. Antidiarrhoeal Activity of Nonanal, an Aldehyde Isolated from Artemisia ludoviciana. Pharmaceutical Biology Volume 40, 2002 - Issue 4.

Nonanal is a clear, brown liquid with a rose-orange scent and is insoluble in water. It is found in at least 20 essential oils, including rose oil, citrus oil, and several pine oils. Nonanal is a saturated fatty aldehyde derived from the reduction of the carboxyl group of nonanoic acid. It is a metabolite observed in cancer metabolism and has been found in both human and plant metabolism. Nonanal is a saturated fatty aldehyde, n-alkane, and medium-chain fatty aldehyde, and its function is related to nonanoic acid. Nonanal has been reported to be found in tea (Camellia sinensis), hops (Humulus lupulus), and several other organisms with relevant data. Nonanal is a uremic toxin. Based on chemical and physical properties, uremic toxins can be classified into three main categories: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small molecule, lipid-soluble compounds and/or protein-bound compounds, such as phenolic compounds; and 3) larger, so-called medium-molecule compounds, such as β2-microglobulins. Long-term exposure to uremic toxins can lead to various diseases, including kidney damage, chronic kidney disease, and cardiovascular disease. Nonanal belongs to the medium-chain aldehyde class. Medium-chain aldehydes are aldehyde compounds with a carbon chain length of 6 to 12 carbon atoms. See also: Aldehydes, C9-11 (note moved to).

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Other information includes nonanal's role as a human and plant metabolite, its function as a growth factor for wood-rotting fungi, and its potential as an attractant for the pine shoot beetle. The compound exhibits antidiarrheal activity and shows significant antibacterial activity against B. cereus and L. monocytogenes (MIC = 7.8 μg/ml). It is observed in cancer metabolism.

C9H18O

142.24

142.135

124-19-6

Nonanal-d18; 1466552-36-2

31289

Colorless to light yellow liquid

0.8±0.1 g/cm3

190.8±3.0 °C at 760 mmHg

145 °F (NTP, 1992) ; -19.3 °C

63.9±0.0 °C

0.5±0.4 mmHg at 25°C

1.418

3.56

0

1

7

10

69.1

0

CCCCCCCCC=O

GYHFUZHODSMOHU-UHFFFAOYSA-N

InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3

nonanal

Nonanal

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 (703.04 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (17.58 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 (17.58 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 (17.58 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.)