| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
The biological target of this compound is generally related to its role as a substrate for enzymes. In the shikimate pathway, it is converted by 3-dehydroshikimate dehydratase to protocatechuic acid. It also has reported antioxidant activity, indicating it can scavenge free radicals and reactive oxygen species. Its mechanism involves transferring hydrogen atoms to neutralize free radicals, thus protecting cells from oxidative stress.
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| ln Vitro |
In vitro, (-)-3-Dehydroshikimic acid exhibits antioxidant activity. This activity can be measured using chemical assays such as the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assay or the ABTS (2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) assay. It neutralizes free radicals, reducing their concentration. This property makes it of interest in research fields focused on preventing oxidative damage.
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| ln Vivo |
No specific in vivo activity for animals is reported for 3-Dehydroshikimic acid alone. Its role is in plant and microbial primary metabolism. In these systems, it is a transient metabolite. Its antioxidant activity may translate to some protective effects in animal models, but this has not been thoroughly studied or reported. Its primary significance is in engineering metabolic pathways in bacteria or yeast.
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| Enzyme Assay |
The compound is not used in standard receptor-binding assays. Its antioxidant activity can be measured in cell-free systems. For the DPPH assay, a solution of DPPH (purple) in ethanol is mixed with the test compound. The decrease in absorbance at 515 nm is measured, as the antioxidant reduces DPPH to DPPH-H (yellow). The radical scavenging activity is calculated as a percentage of inhibition. The IC50 value can be determined.
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| Cell Assay |
For in vitro studies on antioxidant activity, cells (e.g., hepatocytes, neuronal cells) are cultured in media. They are then subjected to oxidative stress using an agent like hydrogen peroxide (H2O2). (-)-3-Dehydroshikimic acid is added to the culture media at varying concentrations (e.g., 10-200 ug/mL) 1-2 hours before the stressor. Cell viability is measured by MTT assay, and intracellular reactive oxygen species (ROS) levels are measured using fluorescent probes like DCFH-DA.
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| Animal Protocol |
No in vivo animal protocols are documented for this compound. It is not a drug candidate. For a basic toxicity or bioavailability study, the compound could be administered to rodents (e.g., 50-200 mg/kg) via oral gavage or intraperitoneal injection. Blood and liver samples could be collected to measure the compound and its metabolites by LC-MS, but such studies are not standard.
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| ADME/Pharmacokinetics |
No specific pharmacokinetic data is available for (-)-3-Dehydroshikimic acid. It is a water-soluble, polar molecule (MW 172.14). It is soluble in water, methanol, and DMSO. For research, it is typically stored as a powder at -20degC. It is a relatively stable compound. For metabolic studies in yeast, it can be added directly to the culture medium.
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| Toxicity/Toxicokinetics |
No specific toxicology data is available for (-)-3-Dehydroshikimic acid. As a naturally occurring intermediate, it is unlikely to be highly toxic. However, standard laboratory safety precautions should be followed. It may be a skin, eye, and respiratory tract irritant. Avoid inhalation, ingestion, and skin contact. The compound is for research use only and not for human or veterinary use.
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| References |
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| Additional Infomation |
3-Dehydroshikimic acid is a 4-oxomonocarboxylic acid, produced by the oxidation of the allyl hydroxyl group of shikimic acid to the corresponding ketone group. It is a plant metabolite. It is a 4-oxomonocarboxylic acid, a 4-hydroxymonocarboxylic acid, a 5-hydroxymonocarboxylic acid, an α,β-unsaturated monocarboxylic acid, and a secondary α-hydroxy ketone. Functionally, it is related to shikimic acid. It is the conjugate acid of 3-dehydroshikimic acid. 3-Dehydroshikimic acid has been reported to exist in common bean (Phaseolus vulgaris), and relevant data are available. 3-Dehydroshikimic acid is a metabolite found or produced in Saccharomyces cerevisiae.
(-)-3-Dehydroshikimic acid is an intermediate in the shikimate pathway, which is crucial for the biosynthesis of aromatic amino acids in plants and microorganisms. It is a research tool for studying metabolic pathways and antioxidant activity. The compound has no approved therapeutic or clinical use and is strictly for laboratory research. |
| Molecular Formula |
C7H8O5
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|---|---|
| Molecular Weight |
172.14
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| Exact Mass |
172.037
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| CAS # |
2922-42-1
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| PubChem CID |
439774
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| Appearance |
Solid powder
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| Density |
1.713g/cm3
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| Boiling Point |
405.1ºC at 760mmHg
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| Flash Point |
213ºC
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| Vapour Pressure |
2.99E-08mmHg at 25°C
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| Index of Refraction |
1.651
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| LogP |
-1.4
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
12
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| Complexity |
255
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C1=C(C[C@H]([C@@H](C1=O)O)O)C(=O)O
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| InChi Key |
SLWWJZMPHJJOPH-PHDIDXHHSA-N
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| InChi Code |
InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1
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| Chemical Name |
(4S,5R)-4,5-dihydroxy-3-oxocyclohexene-1-carboxylic acid
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| Synonyms |
3-DHS; 5-Dehydroshikimic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
H2O : 250 mg/mL (1452.31 mM; with sonication)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.8092 mL | 29.0461 mL | 58.0923 mL | |
| 5 mM | 1.1618 mL | 5.8092 mL | 11.6185 mL | |
| 10 mM | 0.5809 mL | 2.9046 mL | 5.8092 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.
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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