Putresina
Putresina, atau tetramethylenediamine, adalah suatu senyawa kimia organik NH2(CH2)4NH2 (1,4-diaminobutane or butanediamine) yang berbau busuk[1] yang berhuungan dengan kadaverina; keduanya dihasilkan melalui pemecahan asam amino dalam organisme hidup dan mati dan keduanya merupakan racun dalam dosis besar.[2][3] Kedua senyawa tersebut sebagian besar bertanggung jawab atas bau busuk dari daging yang membusuk, namun juga berperan pada bau dari proses seperti bau napas tidak sedap dan vaginosis bakterialis.[4] Mereka juga ditemukan dalam semen dan beberapa mikroalga, bersama dengan molekul terkait seperti spermina dan spermidin.
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| Nama | |
|---|---|
| Nama IUPAC (preferensi)
Butane-1,4-diamine | |
| Nama lain
1,4-Diaminobutane
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| Penanda | |
Model 3D (JSmol)
|
|
| 3DMet | {{{3DMet}}} |
| Referensi Beilstein | 605282 |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| Nomor EC | |
| Referensi Gmelin | 1715 |
| KEGG | |
| MeSH | Putrescine |
PubChem CID
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| Nomor RTECS | {{{value}}} |
| Nomor UN | 2928 |
CompTox Dashboard (EPA)
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|
| |
| |
| Sifat | |
| C4H12N2 | |
| Massa molar | 88,15 g·mol−1 |
| Penampilan | Kristal tak berwarna |
| Bau | kuat, mirip piperidina |
| Densitas | 0,877 g/mL |
| Titik lebur | 27,5 °C (81,5 °F; 300,6 K) |
| Titik didih | 158,6 °C; 317,4 °F; 431,7 K |
| Tercampur | |
| log P | −0,466 |
| Indeks bias (nD) | 1,457 |
| Bahaya | |
| Piktogram GHS |   
|
| Keterangan bahaya GHS | {{{value}}} |
| H228, H302, H312, H314, H331 | |
| P210, P261, P280, P305+351+338, P310 | |
| Titik nyala | 51 °C (124 °F; 324 K) |
| Ambang ledakan | 0,98–9,08% |
| Dosis atau konsentrasi letal (LD, LC): | |
LD50 (dosis median)
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| Senyawa terkait | |
Kecuali dinyatakan lain, data di atas berlaku pada suhu dan tekanan standar (25 °C [77 °F], 100 kPa). | |
 verifikasi (apa ini   ?)
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| Referensi | |
Sejarah
Putresina[5] dan kadaverina[6] pertama kali dilaporkan pada 1885 oleh seorang dokter Berlin, Ludwig Brieger (1849–1919).[7]
Produksi
Putresina diproduksi pada skala industri nelalui hidrogenasi suksinonitril, yang dihasilkan dengan penambahan hidrogen sianida ke akrilonitril.[8] Putrescine is reacted with adipic acid to yield the polyamide Nylon 46, which is marketed by DSM under the trade name Stanyl.[9] Biotechnological production of putrescine from renewable feedstock is a promising alternative to the chemical synthesis. A metabolically engineered strain of Escherichia coli that produces putrescine at high titer in glucose mineral salts medium has been described.[10]
Referensi
- ^ Haglund, William (1996). Forensic taphonomy: The Postmortem Fate of Human Remains. CRC Press. hlm. 100. ISBN 0-8493-9434-1.
- ^ Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. hlm. 212. ISBN 1-56670-223-2.
- ^ Kamhi, Ellen, Ph.D., RN, HNC (2007). Alternative Medicine Magazine's Definitive Guide to Weight Loss. Celestial Arts. hlm. 14. ISBN 1-58761-259-3.
Ornithine is converted by bowel bacteria into a toxic substance called putrescine, which in turn degrades into polyamines, such as spermadine, spermine, and cadaverine (literally meaning "the essence of dead cadavers").
- ^ Yeoman, CJ;Thomas, SM; Miller, ME; Ulanov, AV; Torralba, M; Lucas, S; Gillis, M; Cregger, M; Gomez, A; Ho, M; Leigh, SR; Stumpf, R; Creedon, DJ; Smith, MA; Weisbaum, JS; Nelson, KE; Wilson, BA; White, BA (2013). "A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease". PLOS ONE. 8 (2): e56111. doi:10.1371/journal.pone.0056111. PMC 3566083
. PMID 23405259.
- ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43. From page 43: Ich nenne dasselbe Putrescin, von putresco, faul werden, vermodern, verwesen. (I call this [compound] "putrescine", from [the Latin word] putresco, to become rotten, decay, rot.)
- ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39.
- ^ Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
- ^ "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (edisi ke-7th). Diakses tanggal 2007-09-10.
- ^ "Electronic Control Modules (ECU) - Electrical & Electronics - Applications - DSM". Dsm.com. Diakses tanggal 18 December 2015.
- ^ "Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine". Diakses tanggal 2010-06-10.
