|
|
| | 4-ISOPROPOXYBENZALDEHYDE Basic information |
| | 4-ISOPROPOXYBENZALDEHYDE Chemical Properties |
| Melting point | 167 °C | | Boiling point | 108-110 °C (5 mmHg) | | density | 1.036 | | refractive index | 1.545-1.547 | | Fp | 108-110°C/5mm | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | clear liquid | | color | Colorless to Light orange to Yellow | | Sensitive | Air Sensitive | | BRN | 742921 | | InChI | InChI=1S/C10H12O2/c1-8(2)12-10-5-3-9(7-11)4-6-10/h3-8H,1-2H3 | | InChIKey | WDANSDASCKBVKH-UHFFFAOYSA-N | | SMILES | C(=O)C1=CC=C(OC(C)C)C=C1 | | CAS DataBase Reference | 18962-05-5(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26-36 | | HazardClass | IRRITANT | | HS Code | 2912490090 |
| | 4-ISOPROPOXYBENZALDEHYDE Usage And Synthesis |
| Chemical Properties | clear colorless to yellow liquid | | Uses | ALDH1A3-IN-3 (compound 16) is a potent inhibitor of ALDH1A3, with an IC50 of 0.26 μM. ALDH1A3-IN-3 is also a good ALDH3A1 substrate. ALDH1A3-IN-3 can be used for the research of prostate cancer[1]. | | Synthesis | General procedure for the synthesis of 4-isopropoxybenzaldehyde from 2-iodopropane and p-hydroxybenzaldehyde: Referring to Example 3, to a 100 mL DMF solution containing 2 g (16.38 mmol) of p-hydroxybenzaldehyde was added sequentially 2.72 g (19.69 mmol) of K2CO3, 2.74 g (16.52 mmol) of KI, and 3.94 mL ( 39.38 mmol) 2-iodopropane and the reaction was carried out under argon protection. The reaction mixture was stirred at 80 °C overnight and subsequently concentrated. The concentrated residue was partitioned between CHCl3 and H2O to separate the organic and aqueous phases. The aqueous phase was further extracted with CHCl3 and after combining all the organic phases was dried and concentrated with MgSO4. The crude product was purified by silica gel column chromatography using a gradient polarity EtOAc/hexane mixed solvent as eluent, resulting in 2.08 g of oily 4-isopropoxybenzaldehyde in 77% yield. The structure of the product was confirmed by 1H-NMR (300 MHz, CDCl3, δTMS): 1.39 (d, J=6Hz, 6H), 4.67 (m, 1H), 6.96 (d, J=8.7Hz, 2H), 7.81 (d, J=8.7Hz, 2H), 9.87 (s, 1H). | | IC 50 | ALDH3; ALDH1 | | References | [1] Ibrahim AIM, et, al. Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer. J Med Chem. 2022 Mar 10;65(5):3833-3848. DOI:10.1021/acs.jmedchem.1c01367 |
| | 4-ISOPROPOXYBENZALDEHYDE Preparation Products And Raw materials |
|