Metabolism / Metabolites
Mycobacterium rhodochrous terminally oxidized n-decane to form n-decanal, indicating that initial terminal oxidation was followed by beta-oxidation.
Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Toxicity Summary
IDENTIFICATION AND USE: Decaldehyde (Decanal) is a colorless to light-yellow liquid. The main use of decanal is for citrus tones and for the manufacture of synthetic citrus oils. In addition, the C10 aldehydes have value as intermediates in the synthesis of pharmaceuticals and in the polymer and pesticide fields. In the aircraft cabin, decanal was produced in the presence of ozone from surface reactions with occupants and their clothing, consistent with the inference that occupants were responsible for the removal of >55% of the ozone in the aircraft cabin. HUMAN EXPOSURE AND TOXICITY: Decanal was cytotoxic to Hela cells with IC50 less than 20 ug/mL. ANIMAL STUDIES: Decanal demonstrated antifungal and bactericidal properties. ECOTOXICITY STUDIES: Decanal did not significantly affect survival or hatching success of the brine shrimp Artemia salina.
Uremic toxins such as decanal are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

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Interactions
Environment-selective synergistic toxicity using combinations of aldehydes and hydrazine derivatives was demonstrated in two different model systems in vitro. Combinations of 5-nitro-2-furaldehyde with semi-carbazide and of 2-hydrazinopyridine with pyridine-2-carboxaldehyde, which can react in situ to form antimicrobial hydrazones, demonstrated greater degrees of synergism against the intracellular pathogen, Salmonella typhimurium, at pH 5 relative to pH 7.4. Combinations are more selectively toxic at pH 5 (vs pH 7.4) than individual precursors and preformed hydrazone products because acid catalysis of hydrazone formation plays a role only for the combinations. A combination of decanal and N-amino, N'-octylguanidine (AOG) exhibited more pronounced synergistic cytolytic activity against erythrocytes in 0% serum than in 1% serum. Serum protein binding of decanal inhibited the formation of the more cytotoxic hydrazone, N-decylidenimino,N'-1-octylguanidine (DIOG), from the less cytotoxic AOG and decanal, and serum protein binding of DIOG prevented this cytotoxin from reaching the cell membrane. Because decanal binding cannot play a role in the cytotoxicity of preformed DIOG, it was less selective for cells in 0% serum than the combination of AOG and decanal. The pH 5 and 0% serum environments represent very simple models for macrophage phagolysosomal compartments and poorly vascularized solid tumor interiors respectively. If environment-selective synergism can be used as a basis for target-selective synergism in other in vitro model systems and in vivo, self-assembling combinations could provide a basis for rational introduction of target-selective synergism into chemotherapeutic drug design.
Decanal and N-amino-N'-1-octylguanidine (AOG), combined at 28 microM each, mediated erythrocyte lysis within 80 minutes under physiological conditions. By contrast, no lysis was observed after 20 hours with either decanal (56 microM) or AOG (100 microM) alone. The pronounced synergism observed for these chemicals and similar reactive pairs of chemicals is due to the self-assembly of more cytotoxic hydrazones in situ. Decanal and AOG also exhibit synergistic activity against cultured human cells (HeLa) and bacteria (Escherichia coli J96). This synergism may be useful in the design of cytotoxins that would self-assemble selectively from nontoxic precursors within tumors, while sparing normal tissue.

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Non-Human Toxicity Values
LD50 Rat oral 3730 mg/kg
LD50 Rabbit skin 5040 mg/kg

Toxicity of the bacterial luciferase substrate, n-decyl aldehyde, to Saccharomyces cerevisiae and Caenorhabditis elegans. FEBS Lett. 2001 Oct 5;506(2):140-2.

Decaldehyde is a colorless to light yellow liquid with a pleasant odor. Floats on water. Freezing point is 64 °F. (USCG, 1999)
Decanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of capric acid (decanoic acid). It has a role as an antifungal agent, a fragrance and a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde.
Decanal has been reported in Camellia sinensis, Gymnodinium nagasakiense, and other organisms with data available.
Decanal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Decanal is an organic compound with the chemical formula C9H19CHO. It is the simplest ten-carbon aldehyde. Decanal occurs naturally and is used in fragrances and flavoring. Decanal occurs in nature and is an important component in citrus along with octanal, citral, and sinensal. Decanal is also an important component of buckwheat odour .
Decanal is a metabolite found in or produced by Saccharomyces cerevisiae.
See also: Cynara scolymus leaf (part of).

C10H20O

156.27

156.151

112-31-2

8175

Colorless to light yellow liquid

0.8±0.1 g/cm3

209.0±3.0 °C at 760 mmHg

7 °C

85.6±0.0 °C

0.2±0.4 mmHg at 25°C

1.422

4.09

0

1

8

11

78.9

0

CCCCCCCCCC=O

KSMVZQYAVGTKIV-UHFFFAOYSA-N

InChI=1S/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h10H,2-9H2,1H3

decanal

1-Decyl aldehyde 1-Decanal Decaldehyde

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.

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 (~639.92 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (16.00 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 (16.00 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 (16.00 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.)