By: Ingrid Vacha + Lindsay Spence 12/16/2016 Chemistry 11 Putrescine By: Ingrid Vacha + Lindsay Spence 12/16/2016 Chemistry 11

Molecular Formula Structural Diagram Condensed Structural Formula C4H12N2 Condensed Structural Formula

Who discovered putrescine? Ludwig Brieger a German physician, who lived to be 70 years old (born July 26, 1849 – October 18, 1919), discovered putrescine and cadaverine. Brieger identified these molecules in 1885 during the decomposition of meat. In 1886 the structure for putrescine was confirmed by Albert Ladenburg. Although we are focused on the organic molecule putrescine, cadaverine is very closely related to this compound. Despite the fact that there is not a lot of information regarding Ludwig Brieger, he himself has written many articles on his work. Albert Ladenburg

What is putrescine? Putrescine is a strong and vile smelling odour that is emitted from dead organisms. The systematic name for putrescine is 1, 4- diaminobutane. It is a four carbon chain diamine. Putrescine, alongside cadaverine, is a polyamine. A compound is considered a polyamine when it has two or more primary amino groups. For example, in this case, the functional group with NH2. When nitrogen has one lone pair and 3 bonding electrons, the bonding electrons create single bonds with either hydrogen, aryl or an alkyl group. Because putrescine has two groups, one on each end of the chain, it is then categorized under polyamines. Primary amino group is specifically for nitrogen based atom with a lone pair, and two single bonds to hydrogen.

Why does it smell? Amino acids are considered the “building blocks” of protein. Protein is very important for the human body because it creates a structure for the cells. As mentioned earlier [in the slide before], putrescine gives off a smell that reeks. The reason why this scent is given off is because of the breakdown of amino acids in the bodies. During the process of decomposition, the body releases different amines, and the molecule putrescine is produced. It acts as a repellent to several animals; however, some are attracted to the smell (like flies, and rats).

How is it synthesized Biologically? Putrescine can be found by 3 ways. 1) The bacteria that is produced during the decarboxylation of ornithine, an amino acid [but it is not a protein]. This process is when ornithine changes to putrescine. From there on, putrescine can be converted to spermidine and spermine (2 other polyamines that effect the body differently). Ornithine may be the main compound that produces putrescine, but there are other compounds that’s can take part in the reaction like, methionine and cysteine. 2) In food: Putrescine will begin to develop and the food will start to rot. By adding starter cultures [which leads to fermentation, converts sugar to gas, alcohol or acids] to food, you can indicate the quality of the food. 3) The first, is by formation of putrescine within the human body. Putrescine seemed to interact with DNA. When it tries to bind with the DNA this effects it strength.

The properties of Putrescine Molecular Formula : C4H12N2 Molecular Weight: 88.154 g/mol IUPAC Name: butane-1,4-diamine Melting Point: 27.5 °C Appearance: It is colourless

Use of putrescine in society WITH CANCER The derivatives for putrescine don’t have as bad a contribution when compared to its smell. It is possible that putrescine can “work against” cancer cells. Technically, putrescine can’t work against cancel, but there’s been studies showing the increase of this polyamine in advanced tumours. Also, it appears to increase in body fluids. Using this, scientist may be able to start to detect if there may ever be recurrences (that the cancer could return after treatment). Because one of the processes of the formation of putrescine is by decarboxylation of ornithine, it was detected in tissue cells, for breast cancer. When this occurs too much, too fast in eukaryotic cells (cells that are for the life of organisms), it causes the cells to transform.

Problems with putrescine + Other Facts Putrescine is a polyamide Cell division is regulated by putrescine as well as the differentiation and maturation of cells. Without the help of putrescine, such things would not be possible. Putrescine is also sometimes made into plastics. Scientists produce the putrescine for its industrial uses. It is toxic in large doses. Putrescence is what produces the stench of putrefying flesh but may also produce such doors such as bad breath. It is also found in semen.

Sites https://books.google.ca/books?id=Z5LwCgAAQBAJ&pg=PA1&lpg=PA1&dq=ludwig+brieger+putrescine&source=bl&ots=p4IRW3y2sq&sig=- EQyS8hlCv9_N885OYMmH4s95eU&hl=en&sa=X&ved=0ahUKEwjqg77I3vbQAhUQ9GMKHfPYAs0Q6AEILzAD#v=onepage&q=ludwig%20brieger%20putrescine&f=false https://www.revolvy.com/main/index.php?s=Tetramethylenediamine&item_type=topic http://www.google.ca/url?sa=t&rct=j&q=&esrc=s&source=web&cd=2&sqi=2&ved=0ahUKEwjEtqO17PbQAhUY7GMKHaeLC8wQFggxMAE&url=http%3A%2F%2Fwww.innocua.net%2Fweb%2Fdownload- 1301%2Fcrf312099.pdf&usg=AFQjCNH_6jksTVAHYsII0YpU6KPmM7QA1w&sig2=G0HYGuj19NgoAdkkK829ig&bvm=bv.141536425,d.cGc http://www.infoplease.com/encyclopedia/science/amino-group.html https://en.wikipedia.org/wiki/Polyamine http://www.aminoacid-studies.com/amino-acids/what-are-amino-acids.html http://www.google.ca/url?sa=t&rct=j&q=&esrc=s&source=web&cd=8&ved=0ahUKEwjg3- GCoPrQAhUE3GMKHaVqD7cQFghWMAc&url=http%3A%2F%2Fphysiologyonline.physiology.org%2Fcontent%2Fnips%2F1%2F1%2F12.full.pdf&usg=AFQjCNEDx01PXAlE9w2AFHKBNTXIMgLnlA&sig2=ITOq5 MEfZbS4zXOMz_g1Qw https://www.sciencenews.org/blog/gory-details/why-death-smells-so-deadly http://what-when-how.com/molecular-biology/ornithine-decarboxylase-molecular-biology/ https://www.ncbi.nlm.nih.gov/pubmed/6722462 https://books.google.ca/books?id=ED_xI-CEzFYC&pg=PA62&lpg=PA62&dq=putrescine+is+made&source=bl&ots=QJaVjv9lUC&sig=N- fmoQ1mMIszzt3hdp1DhZiL9MU&hl=en&sa=X&ved=0ahUKEwjozNil0_rQAhXDg1QKHXcZAIgQ6AEILDAC#v=onepage&q=putrescine%20is%20made&f=false https://pubchem.ncbi.nlm.nih.gov/compound/putrescine http://www.hmdb.ca/metabolites/hmdb01414 https://www.goldbio.com/product/1821/putrescine-free-base https://youtu.be/UAldEzWpr_A http://www.rsc.org/images/TM0512-putrescine-cadaverine_tcm18-221656.pdf http://ajpgi.physiology.org/content/278/1/G49