| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Endogenous Metabolite
(S)-2-Hydroxysuccinic acid does not have a primary pharmacological target. It is an endogenous metabolite and a component of the tricarboxylic acid (TCA) cycle. It is used as a food additive and is not a drug. It does not have a defined mechanism of action as a therapeutic agent. |
|---|---|
| ln Vitro |
It has been demonstrated that ME is required for (S)-2-Hydroxysuccinic acid (L-malic acid) consumption in L. casei. Furthermore, deleting either the gene encoding the histidine kinase or the response regulator of the TC system resulted in the loss of the capacity to grow on (S)-2-Hydroxysuccinic acid, demonstrating that the homologous TC system regulates and is required for ME expression. MaeE expression is induced in the presence of (S)-2-Hydroxysuccinic acid and repressed by glucose, whereas TC system expression is induced by (S)-2-Hydroxysuccinic acid but not repressed by glucose[1].
In vitro, (S)-2-Hydroxysuccinic acid is used as a reagent and a standard. It is a component of cell culture media and is used in various biochemical assays. It is not a bioactive compound in the sense of a drug. |
| ln Vivo |
(S)-2-Hydroxysuccinic acid is a naturally occurring compound and is not used as a therapeutic agent in vivo. It is a normal metabolite and is present in the body. It is not administered for pharmacological effects.
|
| Enzyme Assay |
Lactobacillus casei can metabolize L-malic acid via malolactic enzyme (malolactic fermentation [MLF]) or malic enzyme (ME). Whereas utilization of L-malic acid via MLF does not support growth, the ME pathway enables L. casei to grow on L-malic acid. In this work, we have identified in the genomes of L. casei strains BL23 and ATCC 334 a cluster consisting of two diverging operons, maePE and maeKR, encoding a putative malate transporter (maeP), an ME (maeE), and a two-component (TC) system belonging to the citrate family (maeK and maeR). Homologous clusters were identified in Enterococcus faecalis, Streptococcus agalactiae, Streptococcus pyogenes, and Streptococcus uberis. Our results show that ME is essential for L-malic acid utilization in L. casei. Furthermore, deletion of either the gene encoding the histidine kinase or the response regulator of the TC system resulted in the loss of the ability to grow on L-malic acid, thus indicating that the cognate TC system regulates and is essential for the expression of ME. Transcriptional analyses showed that expression of maeE is induced in the presence of L-malic acid and repressed by glucose, whereas TC system expression was induced by L-malic acid and was not repressed by glucose. DNase I footprinting analysis showed that MaeR binds specifically to a set of direct repeats [5'-TTATT(A/T)AA-3'] in the mae promoter region. The location of the repeats strongly suggests that MaeR activates the expression of the diverging operons maePE and maeKR where the first one is also subjected to carbon catabolite repression[1].
(S)-2-Hydroxysuccinic acid is not used in receptor binding or enzyme activity assays as a test agent. It may be used as a standard or a buffer component. |
| Cell Assay |
(S)-2-Hydroxysuccinic acid is not used as a treatment in cell culture experiments. It may be added to cell culture media as a nutrient or a buffer component.
|
| Animal Protocol |
(S)-2-Hydroxysuccinic acid is not administered to animals as a therapeutic agent. It may be used in metabolic studies as a tracer or a standard.
|
| ADME/Pharmacokinetics |
(S)-2-Hydroxysuccinic acid is a naturally occurring metabolite. It is soluble in DMSO (27 mg/mL). It does not have pharmacokinetic properties relevant to drug therapy.
|
| Toxicity/Toxicokinetics |
(S)-2-Hydroxysuccinic acid is a naturally occurring compound and is considered non-toxic. It is a food additive and is generally recognized as safe (GRAS). No significant toxicity has been reported.
|
| References | |
| Additional Infomation |
(S)-malic acid is the optically active form of malic acid with the (S)-configuration and possesses anti-aging properties. It is the conjugate acid of (S)-malic acid (2-) and also the enantiomer of (R)-malic acid. L-malic acid is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). (2S)-2-hydroxysuccinic acid has been reported in Rehmannia glutinosa, pomegranate, and other organisms with relevant data.
(S)-2-Hydroxysuccinic acid is a naturally occurring compound used as a food additive and a research reagent. It has no therapeutic approval status. It is commercially available from chemical suppliers. |
| Molecular Formula |
C4H6O5
|
|---|---|
| Molecular Weight |
134.0874
|
| Exact Mass |
134.021
|
| Elemental Analysis |
C, 35.83; H, 4.51; O, 59.66
|
| CAS # |
97-67-6
|
| Related CAS # |
26999-59-7
|
| PubChem CID |
222656
|
| Appearance |
White to off-white solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
306.4±27.0 °C at 760 mmHg
|
| Melting Point |
127-132 °C
; 130.97 °C /OECD Guideline 102 (Melting point / Melting Range)/
; Crystals; MP: 101 °C /D(+)-Form/
|
| Flash Point |
153.4±20.2 °C
|
| Vapour Pressure |
0.0±1.5 mmHg at 25°C
|
| Index of Refraction |
1.529
|
| Source |
Endogenously produced metabolite
|
| LogP |
-1.26
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
9
|
| Complexity |
129
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C([C@@H](C(=O)O)O)C(=O)O
|
| InChi Key |
BJEPYKJPYRNKOW-REOHCLBHSA-N
|
| InChi Code |
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
|
| Chemical Name |
(2S)-2-hydroxybutanedioic acid
|
| Synonyms |
97-67-6; L-Malic acid; L-(-)-Malic acid; (S)-2-hydroxysuccinic acid; (2S)-2-Hydroxybutanedioic acid; (S)-Malic acid; L(-)-Malic acid; (-)-Malic 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)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~745.77 mM)
H2O : ~100 mg/mL (~745.77 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.64 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (18.64 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (18.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.4577 mL | 37.2884 mL | 74.5768 mL | |
| 5 mM | 1.4915 mL | 7.4577 mL | 14.9154 mL | |
| 10 mM | 0.7458 mL | 3.7288 mL | 7.4577 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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