Uses
4-Hydroxy-1H-indole-3-carbaldehyde is a plant metabolite. 4-Hydroxy-1H-indole-3-carbaldehyde can be isolated from Capparis spinosa L. 4-Hydroxy-1H-indole-3-carbaldehyde can be used in the synthesis of fluorescent probe. 4-Hydroxy-1H-indole-3-carbaldehyde can be used in the study of inflammation-related diseases[1][2][3].
Definition
ChEBI: 4-hydroxyindole-3-carbaldehyde is a heteroarenecarbaldehyde that is 4-hydroxyindole in which the hydrogen at position 3 has been replaced by a formyl group. It has a role as a plant metabolite. It is a member of hydroxyindoles and a heteroarenecarbaldehyde.
Synthesis
Example 1: Synthesis of 4-hydroxy-1H-indole-3-carbaldehyde
1. 7.35 mL of phosphorus oxychloride was slowly added dropwise to 15 mL of dry N,N-dimethylformamide under cooling conditions in an ice-methanol bath with stirring for 15 minutes.
2. 5.0 g of 4-hydroxyindole dissolved in 10 mL of anhydrous N,N-dimethylformamide was added slowly dropwise to the above mixture under cooling in an ice bath.
3. The reaction mixture was stirred at room temperature for 2 hours.
4. Under cooling in an ice bath, water was added to the reaction mixture and adjusted to alkaline with 30% aqueous sodium hydroxide solution and stirring was continued for 15 minutes.
5. The mixture was acidified to pH 4 with 5N hydrochloric acid and the precipitate was collected by filtration.
6. The precipitate was washed with water and dried to give 4.99 g of 4-hydroxy-1H-indole-3-carbaldehyde crude product in 82% yield.
7. The crude product was recrystallized with methanol to give yellow crystals.
Product characterization.
1H-NMR (DMSO-d6) δ: 6.54 (1H, dd, J = 8.1, 0.9 Hz), 6.95 (1H, dd, J = 8.1, 0.9 Hz), 7.13 (1H, t, J = 8.1 Hz), 8.37 (1H, s), 9.64 (1H, s), 10.54 (1H, br s), 12.35 (1H, br s). br s).
Melting point: 190-193 °C.
References
[1] Haifeng Zhou, et al. Anti-inflammatory effects of caper (Capparis spinosa L.) fruit aqueous extract and the isolation of main phytochemicals. J Agric Food Chem. 2010 Dec 22;58(24):12717-21. DOI:
10.1021/jf1034114[2] Weishan Wang, et al. A single fluorescent probe for imaging ribonucleic acid and sulfur dioxide in living systems and its unique application in tumor and normal cells. J Mater Chem B. 2018 Nov 7;6(41):6607-6614. DOI:
10.1039/c8tb02144a[3] Kdimy A, et al. Phytochemistry, Biological Activities, Therapeutic Potential, and Socio-Economic Value of the Caper Bush (Capparis Spinosa L.). Chem Biodivers. 2022 Oct;19(10):e202200300. DOI:
10.1002/cbdv.202200300
