trans-Aconitic acid is present in normal human urine and may be present in large amounts in Reye syndrome and organic aciduria. trans-Aconitic acid is a substrate for trans-pyruvate 2-methyltransferase.

Physicochemical Properties

Molecular Formula	C6H6O6
Molecular Weight	174.1082
Exact Mass	174.016
CAS #	4023-65-8
Related CAS #	(Z)-Aconitic acid-13C6;2456413-64-0
PubChem CID	444212
Appearance	White to off-white solid powder
Density	1.7±0.1 g/cm3
Boiling Point	542.6±50.0 °C at 760 mmHg
Melting Point	190 °C (dec.)(lit.)
Flash Point	296.0±26.6 °C
Vapour Pressure	0.0±3.1 mmHg at 25°C
Index of Refraction	1.571
LogP	0.63
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Heavy Atom Count	12
Complexity	251
Defined Atom Stereocenter Count	0
SMILES	C(/C(=C\C(=O)O)/C(=O)O)C(=O)O
InChi Key	GTZCVFVGUGFEME-HNQUOIGGSA-N
InChi Code	InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+
Chemical Name	(E)-prop-1-ene-1,2,3-tricarboxylic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1]. Quantitation of trans-aconitic acid in different stages of the sugar-manufacturing process. J Agric Food Chem. 2014 Aug 20;62(33):8314-8.

Additional Infomation

Trans-aconitic acid is the trans-isomer of aconitic acid. It has a role as a fundamental metabolite. It is a conjugate acid of a trans-aconitate(3-). trans-Aconitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). trans-Aconitic acid has been reported in Echinochloa phyllopogon, Populus tremula, and other organisms with data available. trans-Aconitic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH. 1. Background of trans-Aconitic acid: trans-Aconitic acid is a natural organic acid present in sugarcane. It is a by-product of the tricarboxylic acid (TCA) cycle in plants and can affect the quality of sugar products (such as color and crystallization) during sugar manufacturing. The study aimed to establish a reliable method for quantifying trans-Aconitic acid to monitor its content changes across different sugar-manufacturing stages [1] 2. Quantitative analysis procedure of trans-Aconitic acid in sugar samples: a. Sample pretreatment: Sugar samples (including sugarcane juice, clarified juice, evaporator syrup, and molasses) were diluted with ultrapure water to an appropriate concentration. Then, 5 mL of the diluted sample was mixed with 1 mL of 0.1 M phosphoric acid (pH 2.5) and vortexed for 1 minute. The mixture was centrifuged at 10,000 × g for 15 minutes at 4°C, and the supernatant was filtered through a 0.22 μm hydrophilic polyethersulfone (PES) membrane to remove impurities [1] b. Chromatographic conditions: High-performance liquid chromatography (HPLC) was used with a C18 reversed-phase column (250 mm × 4.6 mm, 5 μm particle size). The mobile phase was a mixture of 0.1 M phosphoric acid (pH 2.5) and acetonitrile (98:2, v/v) with a flow rate of 1.0 mL/min. The column temperature was maintained at 30°C, and the detection wavelength was set to 210 nm. The injection volume was 20 μL [1] c. Method validation: A standard curve of trans-Aconitic acid was constructed with concentrations ranging from 5 μg/mL to 200 μg/mL, showing a linear correlation coefficient (R²) of 0.9998. The limit of detection (LOD) was 1.2 μg/mL, and the limit of quantification (LOQ) was 3.8 μg/mL. The recovery rate of trans-Aconitic acid in spiked sugar samples ranged from 92.3% to 97.8%, with a relative standard deviation (RSD) of 1.5%–3.2%, indicating good accuracy and precision [1] 3. Content distribution in sugar-manufacturing stages: The study detected trans-Aconitic acid content in different stages: sugarcane juice (12.5–18.3 μg/mL), clarified juice (10.2–15.7 μg/mL), evaporator syrup (85.6–102.4 μg/mL), and molasses (215.3–256.7 μg/mL). The content increased significantly during the evaporation and concentration stages, which was attributed to the reduction of water volume and the stability of trans-Aconitic acid under high-temperature conditions [1]

Solubility Data

Solubility (In Vitro)	H2O : ~100 mg/mL (~574.35 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 50 mg/mL (287.17 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.7435 mL	28.7175 mL	57.4350 mL
	5 mM	1.1487 mL	5.7435 mL	11.4870 mL
	10 mM	0.5743 mL	2.8717 mL	5.7435 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.