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| Other Sizes |
| Targets |
4-HOBA does not have a single well-defined molecular target. It is an isomer of the isoketal scavenger 2-HOBA but has reduced efficacy as an isoketal scavenger. Unlike 2-HOBA, 4-HOBA has no effect on hypertension induced by angiotensin II in mice. It has been used as a negative control for the activity of 2-HOBA and related compounds in a mouse model of hypertension. Potential therapeutic effects of 4-hydroxybenzylamine include its use in the treatment of cancer, neurodegenerative diseases, and cardiovascular disorders.
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| ln Vitro |
In vitro, 4-HOBA has been studied as a less reactive isomer of 2-HOBA. Its reduced efficacy as an isoketal scavenger has been characterized. The compound is an aromatic amine that has been reported to have potential therapeutic effects. However, specific in vitro activity data are limited, as 4-HOBA is primarily used as a negative control compound rather than for its own biological activity.
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| ln Vivo |
In vivo, 4-HOBA attenuated the left ventricular (LV) and lung isolevuglandins (IsoLGs) in mice after transverse aortic constriction (TAC). 4-HOBA effectively attenuated TAC-induced LV hypertrophy, heart failure, and the increase of lung weight in mice, and also improved TAC-induced LV dysfunction. Moreover, 4-HOBA effectively attenuated LV cardiomyocyte hypertrophy, lung inflammation, and lung fibrosis. Unlike 2-HOBA, 4-HOBA has no effect on hypertension induced by angiotensin II in mice.
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| Enzyme Assay |
In non-cell-based biochemical assays, 4-HOBA's activity is evaluated using standard biochemical methods. As an isoketal scavenger, its ability to scavenge isolevuglandins is assessed using mass spectrometry or ELISA-based methods. However, 4-HOBA has reduced efficacy as an isoketal scavenger compared to 2-HOBA. Its purity is assessed using HPLC (99.66%). Its solubility in DMSO (50 mg/mL, 406.01 mM) is characterized.
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| Cell Assay |
In vitro cellular assays for 4-HOBA involve testing its effects on cultured cells. The compound may be used as a negative control in studies of isoketal scavenging and oxidative stress. Cells are treated with 4-HOBA, and endpoints such as cell viability, oxidative stress markers, and inflammatory cytokine production are measured. However, specific cellular assay data are limited, as 4-HOBA is primarily used as a control compound rather than for its own biological activity.
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| Animal Protocol |
In vivo animal studies for 4-HOBA have been conducted in mouse models. In a TAC (transverse aortic constriction) mouse model, 4-HOBA attenuated LV and lung IsoLGs. It effectively attenuated TAC-induced LV hypertrophy, heart failure, and the increase of lung weight, and improved TAC-induced LV dysfunction. 4-HOBA also effectively attenuated LV cardiomyocyte hypertrophy, lung inflammation, and lung fibrosis. Unlike 2-HOBA, 4-HOBA has no effect on hypertension induced by angiotensin II in mice.
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| ADME/Pharmacokinetics |
4-HOBA has a molecular weight of 123.15 and a molecular formula of C7H9NO. It has a density of 1.141 g/cm³. The compound is soluble in DMSO at 50 mg/mL (406.01 mM). For in vivo formulations, 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline at 2 mg/mL (16.24 mM) can be used. Powder should be stored at -20°C for 3 years; in solvent, at -80°C for 1 year.
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| Toxicity/Toxicokinetics |
As a research compound, 4-HOBA is not intended for human use and should be handled with appropriate safety precautions. Comprehensive toxicology studies have not been extensively published. The compound is an endogenous metabolite and is generally considered safe for laboratory use. It should be stored and handled in accordance with standard laboratory safety guidelines.
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| Additional Infomation |
4-Hydroxybenzylamine is an aromatic amine. It has been reported to be present in buckwheat, white mustard, and other organisms for which data is available.
4-HOBA (4-Hydroxybenzylamine) is an endogenous metabolite and an isomer of the isoketal scavenger 2-HOBA. It has reduced efficacy as an isoketal scavenger and has been used as a negative control for the activity of 2-HOBA and related compounds in a mouse model of hypertension. Unlike 2-HOBA, 4-HOBA has no effect on hypertension induced by angiotensin II in mice. Potential therapeutic effects include use in cancer, neurodegenerative diseases, and cardiovascular disorders. |
| Molecular Formula |
C7H9NO
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|---|---|
| Molecular Weight |
123.155
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| Exact Mass |
123.068
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| CAS # |
696-60-6
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| PubChem CID |
97472
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| Appearance |
White to light brown solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
262.4±15.0 °C at 760 mmHg
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| Melting Point |
116-118ºC
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| Flash Point |
112.5±20.4 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.594
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| LogP |
0.35
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
9
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| Complexity |
77
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
RQJDUEKERVZLLU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H9NO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H,5,8H2
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| Chemical Name |
4-(aminomethyl)-phenol
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| Synonyms |
4-Hydroxybenzylamine4-HOBA 4-(Aminomethyl)phenol
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 (~812.02 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (20.30 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 (20.30 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 (20.30 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 | 8.1195 mL | 40.5976 mL | 81.1952 mL | |
| 5 mM | 1.6239 mL | 8.1195 mL | 16.2390 mL | |
| 10 mM | 0.8120 mL | 4.0598 mL | 8.1195 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05274243 | RECRUITING | Drug: 2-HOBA Other: Placebo |
Rheumatoid Arthritis | Vanderbilt University Medical Center | 2022-08-09 | Phase 2 |
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