| Size | Price | Stock | Qty |
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| 500mg |
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| Other Sizes |
| ln Vitro |
4-Hydroxymandelic acid (4-HMA) is frequently utilized in the creation of fragrant medications and scents. used to make 4-hydroxyphenylacetic acid, the synthetic precursor of the medication atenolol, a selective β1-receptor antagonist. This p-hydroxymandelic acid-based linker system exhibits a wide range of application prospects in targeted drug delivery systems, since it may be attached to cytotoxic medicines and enzyme substrates [1].
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| Enzyme Assay |
The study describes the function of the heterologously expressed 4-hydroxymandelate synthase (HmaS, from Amycolatopsis orientalis, codon-optimized as shmaS) in engineered E. coli. HmaS is an α-keto acid-dependent dioxygenase that catalyzes the conversion of 4-hydroxyphenylpyruvate (4-HPP) to 4-HMA via oxidative decarboxylation, incorporating molecular oxygen. The enzymatic activity was confirmed by detecting the production of 4-HMA in recombinant E. coli strain culture supernatants using HPLC and LC-MS analysis, comparing retention time and mass-to-charge ratio (m/z 167, [M-H]⁻) with a commercial standard. [1]
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| Cell Assay |
Fermentation Process (Microbial Cell Factory): Engineered E. coli strains (e.g., HMA15) were cultivated in shake flasks or a 5L bioreactor using defined mineral salt media. Cell growth was monitored by measuring optical density at 600 nm (OD₆₀₀). For shmaS expression under the T7 promoter, induction with IPTG was avoided as it inhibited growth; expression was constitutive under the control of gap, trc, or lacUV5 promoters. Fed-batch fermentation was performed by feeding a solution containing glucose and xylose to maintain residual sugar levels. Broth samples were periodically taken, centrifuged, and filtered for analysis of metabolites (4-HMA, acetate) and residual sugars (glucose, xylose). [1]
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| References | |
| Additional Infomation |
4-Hydroxymandelic acid (4-HMA) is a 2-hydroxycarboxylic acid compound with a phenolic hydroxyl group at the 4-position of mandelic acid. It is a metabolite. It belongs to the 2-hydroxycarboxylic acid family and is also a phenolic compound. Functionally, it is related to mandelic acid. It is the conjugate acid of 4-hydroxymandelic acid ester. 4-HMA is an important aromatic fine chemical with wide applications in the pharmaceutical and food industries. It is a precursor for the synthesis of compounds such as 4-hydroxyphenylacetic acid, which is a raw material for the synthesis of the β1-receptor antagonist atenolol. 4-HMA can also be used in adapter systems for targeted drug delivery. Its derivatives, such as polyhydroxymandelic acid amide, have reported free radical scavenging (antioxidant) activity. Furthermore, 4-hydroxymethylacrylic acid (4-HMA) can be enzymatically converted into the widely used flavoring agent ethyl vanillin. Traditionally, the production of 4-HMA has employed an environmentally unfriendly chemical condensation process using glyoxylic acid and phenol. This study proposes a biomanufacturing alternative, namely, the metabolic engineering of Escherichia coli strains to enable them to produce 4-HMA using renewable sugars (glucose and xylose). The final engineered strain, HMA15, had its ptsG, pykA, pykF, tyrR, pheA, tyrB, and aspC genes knocked out, and expressed optimized shmaS and other pathway genes. This strain achieved a 4-HMA yield of 15.8 g/L in 60 hours using a glucose-xylose mixture via fed-batch fermentation. This study shows that the co-utilization of glucose and xylose (the main components of lignocellulose biomass hydrolysate) can be used for sustainable production. [1]
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| Molecular Formula |
C8H8O4
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|---|---|
| Molecular Weight |
168.1467
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| Exact Mass |
168.042
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| CAS # |
1198-84-1
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| PubChem CID |
328
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| Appearance |
White to pink solid powder
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| Density |
1.48 g/cm3
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| Boiling Point |
405.4ºC at 760 mmHg
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| Melting Point |
82-85 °C(lit.)
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| Flash Point |
213.1ºC
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| LogP |
0.51
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
160
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
YHXHKYRQLYQUIH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
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| Chemical Name |
2-hydroxy-2-(4-hydroxyphenyl)acetic 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) |
DMSO : ~22.22 mg/mL (~132.14 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.22 mg/mL (13.20 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 22.2 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: ≥ 2.22 mg/mL (13.20 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 22.2 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.9471 mL | 29.7354 mL | 59.4707 mL | |
| 5 mM | 1.1894 mL | 5.9471 mL | 11.8941 mL | |
| 10 mM | 0.5947 mL | 2.9735 mL | 5.9471 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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