11-Aminoundecanoic acid

Description

Aminoundecanoic acid can be used as a PROTAC linker in the synthesis of PROTACs. Aminoundecanoic acid is an alkane chain with terminal carboxlic acid and amine groups. The amino group (NH2) is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The terminal carboxylic acid can react with primary amine groups of activated NHS ester to form a stable amide bond.

Chemical properties

White crystalline powder

Chemical properties

11-Aminoundecanoic acid is a solid.

The Uses of 11-Aminoundecanoic acid

11-Aminoundecanoic Acid is used to prepare thapsigargin analogues targeting apoptosis to prostatic cancer cells. It is also used to synthesize N-carboxyalkylpeptides containing extended alkyl residues at P1''as matrix metalloproteinase inhibitors.

Preparation

|?-Aminoundecanoic acid is normally prepared from castor oil (glycerol triricinoleate). Firstly the castor oil is subjected to methanolysis to yield the methyl ester of ricinoleic acid and then the following route is used:

In the first step, the pyrolysis of methyl ricinoleate is carried out at about 500??C; the principal products are n-heptaldehyde and methyl undecylenate. The latter is hydrolysed to give undecylenic acid which is treated with hydrogen bromide in a non-polar solvent in the presence of a peroxide. Under these conditions, reverse Markownikoff addition occurs and the main product is |?-bromoundecanoic acid. This product is then treated with ammonia to give |?-aminoundecanoic acid, which is a crystalline solid, m.p. 189??C.

Definition

ChEBI: 11-Aminoundecanoic acid is a medium-chain fatty acid.

General Description

White crystalline solid or powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

11-Aminoundecanoic acid is incompatible with strong oxidizing agents, strong acids and strong bases.

Fire Hazard

Flash point data for 11-Aminoundecanoic acid are not available; however, 11-Aminoundecanoic acid is probably combustible.

Flammability and Explosibility

Non flammable

Safety Profile

Poison by ingestion. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.