Uses
N-[2-(4-Hydroxyphenyl)ethyl]acetamide maintains anti-tumor properties and is derived from a marine bacterium named Streptoverticillium. Cytotoxin.
Definition
ChEBI: N-acetyltyramine is a member of the class of tyramines that is tyramine in which one of the hydrogens of the amino group is replaced by an acetyl group. It has a role as a marine metabolite, a bacterial metabolite, an Aspergillus metabolite, an animal metabolite and a quorum sensing inhibitor. It is a member of acetamides and a member of tyramines. It is functionally related to a tyramine.
Synthesis
General Steps:
1. In a dry reaction flask, add p-hydroxyphenethylamine and an appropriate amount of anhydrous dichloromethane and stir to dissolve.
2. Place the reaction vial in an ice-water bath and cool to 0-5°C. Slowly add the acetic anhydride dropwise, controlling the rate of addition to maintain a reaction temperature of not more than 10°C.
3. After the dropwise addition is complete, remove the ice water bath, allow the reaction mixture to warm slowly to room temperature, and continue to stir the reaction for 2-3 hours.
4. Upon completion of the reaction, the reaction mixture was poured into ice water and the pH adjusted to neutral with dilute hydrochloric acid.
5. The aqueous phase was extracted with dichloromethane, the organic phases were combined and dried over anhydrous sodium sulfate.
6. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give the crude product N-acetyltyramine.
7. The crude product can be further purified by column chromatography or recrystallization.
References
[1] Patent: US9522908, 2016, B2. Location in patent: Page/Page column 57
[2] Biochemical Pharmacology, 1998, vol. 55, # 1, p. 37 - 43
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 1, p. 83 - 89
