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| Other Sizes |
| Targets |
3-Hydroxyphthalic anhydride does not have a defined pharmacological target of its own, as it is a chemical reagent. Its mechanism of action is chemical: the anhydride group reacts with nucleophiles (e.g., amines) to form amide bonds, enabling protein modification and bioconjugation. The hydroxyl group can participate in further derivatization reactions. The compound is used to synthesize 3-hydroxyphthalic anhydride-modified human serum albumin as a microbicide for preventing sexual transmission of HIV.
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| ln Vitro |
In vitro, 3-hydroxyphthalic anhydride is used as a chemical reagent for protein modification and bioconjugation. It is employed to modify proteins and peptides, particularly in the development of enzyme inhibitors and antigen carriers for immunological research and vaccine design. The compound is also used in the preparation of polyimides, functionalized pigments, and bioconjugation reagents.
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| ln Vivo |
In vivo data for 3-hydroxyphthalic anhydride as a therapeutic agent are limited. The compound has been used to synthesize 3-hydroxyphthalic anhydride-modified human serum albumin, which has high potency as a microbicide for prevention of the sexual transmission of HIV. Specific in vivo pharmacokinetic and pharmacodynamic data for the compound itself are not well-documented.
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| Enzyme Assay |
For in vitro protein modification, 3-hydroxyphthalic anhydride is used to modify proteins and peptides. Standard protocols involve dissolving the compound in an appropriate solvent (e.g., DMSO, DMF) and adding it to the protein solution in buffer (e.g., PBS, pH 7.4-8.5). The reaction is incubated at room temperature for 1-4 hours. The degree of modification is assessed by MALDI-TOF mass spectrometry or by measuring the change in protein charge using SDS-PAGE or isoelectric focusing.
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| Cell Assay |
For in vitro cell-based experiments, 3-hydroxyphthalic anhydride is not typically used directly in cell culture. It is a chemical reagent used for protein modification and bioconjugation. The compound may be used in the synthesis of modified proteins or bioconjugates that are subsequently tested in cell-based assays, but it is not added directly to cell cultures as a test compound.
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| Animal Protocol |
In vivo animal studies using 3-hydroxyphthalic anhydride are conducted on the modified proteins or bioconjugates synthesized from it, not on the compound itself. For HIV microbicide candidates derived from this building block, efficacy studies would typically be performed in mouse models of HIV transmission. Standard in vivo protocols involve topical or systemic administration of the modified protein, with measurement of viral transmission and immune responses.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 3-hydroxyphthalic anhydride are not available, as the compound is a chemical reagent used for protein modification rather than a drug candidate. The compound has a molecular weight of 164.12 g/mol. As a reactive anhydride, it would be rapidly hydrolyzed in aqueous environments to the corresponding dicarboxylic acid. The compound is primarily used as a reagent rather than as a drug candidate.
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| Toxicity/Toxicokinetics |
3-Hydroxyphthalic anhydride is a research chemical and should be handled with appropriate laboratory safety precautions. As a reactive anhydride, it may cause skin and eye irritation. The compound is for research use only and not for human therapeutic or diagnostic applications. Specific LD₅₀ values, acute toxicity classifications, and chronic toxicity data are not available in the public literature. Standard safety practices include the use of personal protective equipment and working in a fume hood.
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| Additional Infomation |
Used to modify proteins
3-Hydroxyphthalic anhydride (CAS 37418-88-5) is primarily a research-grade chemical reagent, not an FDA-approved pharmaceutical drug. Its primary applications are in protein modification and bioconjugation, in the development of enzyme inhibitors and antigen carriers, and in the preparation of polyimides and functionalized pigments. It has been used to synthesize HIV microbicide candidates. No clinical trials or approved therapeutic indications exist. |
| Molecular Formula |
C8H4O4
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|---|---|
| Molecular Weight |
164.12
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| Exact Mass |
164.01
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| CAS # |
37418-88-5
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| PubChem CID |
96580
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| Appearance |
Solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
365.4±25.0 °C at 760 mmHg
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| Melting Point |
199-202 °C(lit.)
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| Flash Point |
160.2±16.7 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.666
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| LogP |
0.86
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
12
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| Complexity |
235
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC2=C(C(=C1)O)C(=O)OC2=O
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| InChi Key |
CCTOEAMRIIXGDJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H4O4/c9-5-3-1-2-4-6(5)8(11)12-7(4)10/h1-3,9H
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| Chemical Name |
4-hydroxy-2-benzofuran-1,3-dione
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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: 100 mg/mL (609.31 mM)
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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 | 6.0931 mL | 30.4655 mL | 60.9310 mL | |
| 5 mM | 1.2186 mL | 6.0931 mL | 12.1862 mL | |
| 10 mM | 0.6093 mL | 3.0466 mL | 6.0931 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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