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Traumatic Acid

Cat No.:V40183 Purity: ≥98%
Traumatic Acid is a wound healing agent and a cytokinin (phytohormone).
Traumatic Acid
Traumatic Acid Chemical Structure CAS No.: 6402-36-4
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
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Product Description
Traumatic Acid is a wound healing agent and a cytokinin (phytohormone). Traumatic Acid enhances collagen biosynthesis in cultured human skin fibroblasts. Traumatic Acid inhibits the survival rate of MCF-7 breast cancer/tumor cells and enhances apoptosis and oxidative stress. Traumatic Acid may be utilized in study/research of cancer, circulatory diseases (including arterial hypertension), and skin diseases related to oxidative stress and disorders of collagen biosynthesis.
Traumatic Acid (trans-2-dodecenedioic acid) is a naturally occurring monounsaturated dicarboxylic acid found in certain plants, particularly in the genus Echinacea. It is a wound healing agent and a cytokinin (phytohormone) that stimulates cell division near a wound site to form a protective callus in plants. It has a molecular weight of 228.28 g/mol and a molecular formula of C12H20O4.
Biological Activity I Assay Protocols (From Reference)
Targets
Traumatic Acid does not have a classical pharmacological target in mammals. It is a plant hormone (cytokinin) that promotes wound healing by stimulating cell division at trauma sites. In mammalian systems, it enhances collagen biosynthesis in cultured human skin fibroblasts and inhibits the survival of MCF-7 breast cancer cells by enhancing apoptosis and oxidative stress.
ln Vitro
Fibroblast cell count is dramatically increased by wound acid (0.1, 1 µM; 5 days) [1]. In fibroblasts, traumatic acid (0.1, 1 µM; 5 days) decreases glutathione level, increases GPX activity, and lessens membrane phospholipid peroxidation [1]. In fibroblast culture media, traumatizing acid (0.1, 1 µM; 5 days) increases collagen secretion and synthesis [1]. The number of viable cells was dramatically decreased by wound acid (100, 200, 400, and 600 µM; 48 hours), particularly following treatment at 100 µM and 200 µM for 48 hours in MCF-7 cells [2]. In MCF-7 cells, traumatic acid (50–600 µM; 24–48 hours) promotes apoptosis and reduces cell viability in a dose- and time-dependent manner [2]. In MCF-7 cells, traumatic acid (50–200 µM; 24–48 hours) oxidatively damages proteins [2]. The oxidative stress level of MCF-7 cells can be efficiently increased by traumatic acid (100, 200 µM; 24, 48 hours) [2].
In vitro, Traumatic Acid enhances collagen biosynthesis in cultured human skin fibroblasts. It inhibits the survival rate of MCF-7 breast cancer cells and enhances apoptosis and oxidative stress. The compound also functions as a wound healing agent in plants, stimulating cell division to form a protective callus.
ln Vivo
In vivo, Traumatic Acid has been studied for its effects on tissue repair and wound healing. It may offer therapeutic benefits in treating inflammatory conditions, skin injuries, and certain autoimmune disorders. Topical application of trans-traumatic acid has been shown to have important effects on the healing and closure of diabetic wounds in a streptozotocin-induced diabetic mouse model.
Enzyme Assay
In vitro assays for Traumatic Acid typically involve measuring its effects on cell proliferation and collagen synthesis. Human skin fibroblasts are cultured and treated with the compound at various concentrations. Collagen biosynthesis is measured by ELISA or by incorporating radiolabeled proline. Cell viability is assessed by MTT or standard assays. Apoptosis is evaluated by Annexin V/PI staining and caspase-3/7 activity assays.
Cell Assay
Cell Proliferation Assay[1]
Cell Types: Fibroblasts
Tested Concentrations: 0.1, 1 µM
Incubation Duration: 5 days
Experimental Results: Caused a significant increase in cell number, especially on day 1 at a concentration of 1 µM. Compared to untreated control cells, cell numbers increased by 133% and 118% at concentrations of 1 and 0.1 µM, respectively.
Cell viability assay[1]
Cell Types: Fibroblasts
Tested Concentrations: 0.1, 1 µM
Incubation Duration: 5 days
Experimental Results: Total protein content increased by 183% and 90% on day 1 compared to controls at concentrations of 1 and 0.1 µM, respectively . Collagen increased compared to control by 72% at 0.1 µM (day 3) and 51% at 1 µM (day 1). Compared to the control, GPX activity increased by 111% and 97% at concentrations of 1 and 0.1 µM, respectively. The diminished glutathione content increased by 86% and 80% at 0.1 µM and 1 µM, respectively. Reduce membrane phospholipid peroxidation.
Cell viability assay [2]
Cell Types: MCF-7 Cell
Tested Concentrations: 100, 200, 400, 600 µM
Incubation Duration: 4
For in vitro cell-based assays, MCF-7 breast cancer cells are cultured and treated with Traumatic Acid at various concentrations. Cell viability is assessed by MTT or standard assays. Apoptosis is evaluated by Annexin V/PI staining, caspase-3/7 activity assays, and oxidative stress markers. The compound's effects on collagen synthesis can be assessed in fibroblast cultures.
Animal Protocol
In vivo animal studies with Traumatic Acid are conducted in models of wound healing, particularly diabetic wound healing. Topical application of trans-traumatic acid in a streptozotocin-induced diabetic mouse model promotes wound closure. The compound's effects on tissue repair and inflammation are assessed by measuring wound size, histopathological analysis, and inflammatory markers.
ADME/Pharmacokinetics
Traumatic Acid (CAS: 6402-36-4) has a molecular weight of 228.28 g/mol and a molecular formula of C12H20O4. IUPAC name: (E)-dodec-2-enedioic acid. Appearance: solid. Melting point: 192-195°C. Storage: room temperature. The compound is a naturally occurring wound healing agent and phytohormone.
Toxicity/Toxicokinetics
Traumatic Acid is a naturally occurring compound and is considered to have a low toxicity profile. It is used as a research compound and is not intended for human therapeutic use. In preclinical studies, it has shown potential for wound healing and anti-cancer applications. Standard laboratory safety precautions should be followed when handling the compound.
References

[1]. Traumatic Acid Reduces Oxidative Stress and Enhances Collagen Biosynthesis in Cultured Human Skin Fibroblasts.Lipids. 2016 Sep;51(9):1021-35.

[2]. Traumatic acid toxicity mechanisms in human breast cancer MCF-7 cells. Regul Toxicol Pharmacol. 2019 Aug;106:137-146.

Additional Infomation
Wound healing acid is a monounsaturated straight-chain dicarboxylic acid with a double bond located at the C-2 position; it is a plant wound healing hormone and functions as a plant hormone. Wound healing acid has been reported in Meehania urticifolia, and relevant data are available for reference.
Traumatic Acid (trans-2-dodecenedioic acid) is a naturally occurring monounsaturated dicarboxylic acid that functions as a wound healing agent and cytokinin (phytohormone). It enhances collagen biosynthesis in human skin fibroblasts and inhibits MCF-7 breast cancer cell survival. It has a molecular weight of 228.28 g/mol and a molecular formula of C12H20O4. It is not FDA-approved and is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H20O4
Molecular Weight
228.2848
Exact Mass
228.136
CAS #
6402-36-4
PubChem CID
5283028
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
376.4±15.0 °C at 760 mmHg
Melting Point
165-167 °C(lit.)
Flash Point
195.6±16.9 °C
Vapour Pressure
0.0±1.8 mmHg at 25°C
Index of Refraction
1.493
LogP
2.95
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
10
Heavy Atom Count
16
Complexity
233
Defined Atom Stereocenter Count
0
SMILES
C(CCCCC(=O)O)CCC/C=C/C(=O)O
InChi Key
MAZWDMBCPDUFDJ-VQHVLOKHSA-N
InChi Code
InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7+
Chemical Name
(E)-dodec-2-enedioic 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

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~1095.15 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.11 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 20.8 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: ≥ 2.08 mg/mL (9.11 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 20.8 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: ≥ 2.08 mg/mL (9.11 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 20.8 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.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.3806 mL 21.9029 mL 43.8059 mL
5 mM 0.8761 mL 4.3806 mL 8.7612 mL
10 mM 0.4381 mL 2.1903 mL 4.3806 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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