Cadaverine, odor

One other characteristic of amines is their odor. Low-molecular-weight amines such as trimethyjamine have a distinctive fishlike aroma, while diamines such as 1,5-pentanediamine, commonly called cadaverine, have the appalling odors you might expect from their common names. 

However, there may be a type of poisoning that does not arise from high levels of histamine, therefore a low histamine level may not be an absolute assurance of product safety. It may be more appropriate to state that the absence of decomposition in the fish renders it a safe product. As such, a safe product would have no evidence of spoilage, including odors of decomposition, high histamine levels, or other amines, e.g. cadaverine. 

As you might guess from their names, these molecules have notably unpleasant odors. They were initially identified as degradation products of the action of bacteria on animal tissue. Cadaverine is also notably toxic. Putrescine is found in most cell types and is a precursor to spermidine. Note that both molecules have two amino groups. 

One of the most notable physical properties of many low-formula-mass amines is their offensive odor. Figure 12.16 on page 406 shows two appropriately named amines, putrescine and cadaverine, responsible for the odor of decaying flesh. 

Cadaverine is an organic compound that has a strong, disagreeable odor. Treatment of 15.00 mL of a smelly solution with 1.75 mL of 5M HC1 wiped out the odor (your nose was the indicator), (a) What was the normality of the smelly solution (b) Why didn t this question ask for molarity, rather than normality ... 

There are a number of similarities between ammonia and amines that carry beyond the structure. Consider odor. The smell of amines resembles that of ammonia but is not as sharp. However, amines can be quite pungent. Anyone handling or working with raw fish knows how strong the amine odor can be, since raw fish contains low-molecular-weight amines such as dimethylamine and trimethylamine. Other amines associated with decaying flesh have names suggestive of their odors putrescine and cadaverine. 

Lysine Does not transaminate Cadaverine Cadaverine is toxic and has odor of rotting flesh... 

Another charaetehabc of amines is thetr odor. Low-molecular-m amines such as trimethjdamtnc have a distinctive fishlike aroma, diamines such as cadaverine I l,S-pentanediamine) have names that are sdf explanatory. 

Another type of electronic nose was developed at Lund University in Sweden specifically to detect the odors associated with spoiled fish. In this case the sensor uses two enzymes linked to a polymer to detect the presence of amines such as histamine, putrescine, and cadaverine. Such amines are produced by microbes as fish spoil. 

Many amines have unpleasant fishlike odors. For example, the odors associated with decaying animal and human tissues are caused by amines such as putrescine (FUNCH >CFUCH2NI-U) and cadaverine (H2NCH2CH2CH2CH2CH2NH2). 

Many low molecular weight amines have very foul odors. Trimethylamine [(CH3)3N], formed when enzymes break down certain fish proteins, has the characteristic odor of rotting fish. Putrescine (NH2CH2CH2CH2CH2NH2) and cadaverine (NH2CH2CH2CH2CH2CH2NH2) are both poisonous diamines with putrid odors. They, too, are present in rotting fish, and are partly responsible for the odors of semen, urine, and bad breath. 

All volatile amines have odors that humans find offensive, and amines are responsible for many of the odors characteristic of dead, decaying organisms. Two amines found in decaying human remains are putres-cine and cadaverine. Specially trained dogs are used to locate human remains using these distinctive odors. Sniffer dogs are often used after catastrophic events, such as tsunamis, hurricanes, and earthquakes. They are also used in forensic investigations. 

Sometimes amines have rather creative names that are suggestive of their odors It should not he dfi cult to imagine what cadaverine and putrescine smell like ... 

By the way. all these nice, tidy analogies do not extend to the smells possessed by most amines. Whereas alcohols tend to have, at worst, somewhat heavy, sweetish odors, amines, at best, smell like ammonia, and, at worst, richly deserve the common names that have been bestowed upon some of their representatives. These include names like cadaverine. putrescine. and skatole. Dead fish would be an improvement. 

Cadaverine (1,5-pentanediamine). H2N-(CH2)s-NH2, CsH,4N2, Mr 102.18, mp. 9°C, bp. 178-180°C. C. is a polyamine, formed by bacteria through decarboxylation of lysine in the gastrointestinal system or on putrefaction of cadavers, contributing to the odor of putrefaction. It is the biosynthetic precursor of some alkaloids see also quinolizidine alkaloids. Lycopodium alkaloids, piperidine alkaloids. 

Amines and NH3 are produced by the anaerobic (absence of O2) decomposition of dead animal or plant matter. Two such amines with very disagreeable odors are H2N(CH2)4NH2, putresciiie, and H2N(CH2)5NH2, cadaverine. 

We hypothesized that compounds that attract brown tree snakes could be those that are considered major components of the odor of carrion. These include cadaverine, di-methylamine, dimethyl disulfide, dimethyl sulfide, ethanethiol, trimethylamine, and putre-scine, (Eskin, Henderson Townsen, 1971 Stager, 1964). For testing, we chose odor concentrations that were easily detectable, but not overpowering, to the human nose. 

Cadaverine, 1,5-diaminopentane a poisonous biogenic amine produced enzymatically by decarboxylation of lysine. C. is a precnrsor of certain alkaloids, and it is one of the compounds responsible for the odor of decaying meat and fecal matter. It is the preferred substrate of the amine oxidase EC I.4.3.6. 

Almost all of the low-molecular-weight amines have objectionable (to humans) odors. Many of the compounds smell fishy and, indeed, the odor of rotting fish has been attributed to such materials. Some diamines produced by the action of bacteria on decaying organic materials enjoy names refiective of their unpleasant odors, for example, putrescine [H2N(CH2)4NH2] and cadaverine [H2N(CH2)5NH2]. 

Amines with sufficient vapor pressure are reported to have unpleasant odors. Some low-molecular-weight amines are reported to have an odor resembling ammonia by some and simply fishy by others. Putrefaction of proteins produces toxic materials (ptomaines), and the bis-primary amines 1,4-diaminobutane (H2NCH2CH2CH2CH2NH2, putrescine) and its homologue, 1,5-diaminopentane [H2N(CH2)5NH2, cadaverine], are materials whose trivial names announce their presence in the decaying matter and whose odors are considered so unpleasant that most humans avoid putrescent materials. 

Amines are best known for their awful odors. When a living organism dies, bacteria that feast on its proteins emit amines. For example, trimethylamine is a component of the smell of rotten fish, and cadaverine and putrescine are responsible for the smell of deca5ung animal flesh. 

Amines with low molecular weights, such as trimethylamine, typically have a fishlike odor. In fact, the odor of fish is caused by amines that are produced when enzymes break down certain fish proteins. Putrescine and cadaverine are examples of compounds present in rotting fish. They are also present in urine, contributing to its characteristic odor. 

These microorganisms generate a wide array of compounds that contribute to whole fish spoilage and produce many off-odor and off-flavor compounds such as biogenic amines (putrescine, cadaverine, and histamine), hydroxylamine, ketones, aldehydes, alcohols, and organic acids that are essentially absent or only occur at very low levels in fresh fish (Ghaly et al., 2010). 

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