1,5-Diaminopentane

Description

Yes, it’s what you think it is: a foul-smelling compound found in putrefying animal tissue. Cadaverine, or 1,5-pentanediamine, is formed by the decarboxylation of the amino acid lysine. It and its companion decomposition product putrescine (1,4-butanediamine) also contribute to odors associated with bad breath, urine, semen, and bacterial vaginosis.

Chemical properties

colourless to light yellow liquid with a very unpleasant smell

The Uses of 1,5-Diaminopentane

1,5-Diaminopentane is mainly used in organic synthesis.

The Uses of 1,5-Diaminopentane

Cadaverine is a diamine that can be used in hetarylation with halopyridines (2-bromo, 2-iodo, and 3-iodo-pyridines) to synthesize N,N′-dipyridinyl diamine derivatives in the presence of CuI-2-isobutyrylcyclohexanone as a catalyst. It can also be used to synthesize a poly-imidazolium polymer with high thermal stability by reacting with acetic acid, pyruvaldehyde and formaldehyde by modified Debus-Radziszewski reaction.

Production Methods

1,5-Diaminopentane can be prepared by methods similar to those described for 1,4-diaminobutane. The starting materials are 1,5-dichloropentane (obtainable from tetrahydropyran), glutarodinitrile, or glutaraldehyde. The compound is hygroscopic and has a very bad odor.

What are the applications of Application

Cadaverine is a biogenic amine

Definition

ChEBI: An alkane-alpha,omega-diamine comprising a straight-chain pentane core with amino substitutents at positions 1 and 5. A colourless syrupy liquid diamine with a distinctive unpleasant odour, it is a homologue of putresceine and is formed by the bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. It is also found in plants such as soyabean.

General Description

Cadaverine, a biogenic amine, belongs to the class of aliphatic diamines and is commonly found in food products including cheese, fish products, fermented sausages, fish sauces, etc. It can be used as a freshness marker and as an indicator of microbial spoilage since it is most commonly identified in food products as a result of inappropriate storage conditions and microbial contamination.

Flammability and Explosibility

Not classified

Safety Profile

Poison by intravenous, rectal, and subcutaneous routes. Moderately toxic by skin contact. An irritant, sensitizer, and allergen. Mutagenic data. When heated to decomposition it emits highly toxic fumes of NOx.

Purification Methods

Purify the base by distillation, after standing over KOH pellets (at room temperature, i.e. liquid form). Its dihydrochloride has m 275o (sublimes in a vacuum), and its tetraphenyl boronate has m 164o. [Schwarzenbach et al. Helv Chim Acta 35 2333 1952, Beilstein 4 IV 1310.]