カダベリン
WordNet
- a colorless toxic ptomaine with an unpleasant odor formed during the putrefaction of animal tissue
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/08/22 10:36:32」(JST)
[Wiki en表示]
Cadaverine
|
|
| Names |
| Preferred IUPAC name
|
| Other names
1,5-Diaminopentane
|
| Identifiers |
|
CAS Number
|
|
|
3D model (JSmol)
|
|
| 3DMet |
B00334 |
|
Beilstein Reference
|
1697256 |
| ChEBI |
|
| ChemSpider |
|
| DrugBank |
|
| ECHA InfoCard |
100.006.664 |
| EC Number |
207-329-0 |
|
Gmelin Reference
|
2310 |
| KEGG |
|
| MeSH |
Cadaverine |
|
|
|
| RTECS number |
SA0200000 |
| UNII |
|
| UN number |
2735 |
InChI
-
InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 Y
Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N Y
|
|
|
| Properties |
|
Chemical formula
|
C5H14N2 |
| Molar mass |
102.18 g·mol−1 |
| Appearance |
colourless to yellow oily liquid |
| Odor |
unpleasant |
| Density |
0.8730 g/mL |
| Melting point |
11.83 °C (53.29 °F; 284.98 K) |
| Boiling point |
179.1 °C; 354.3 °F; 452.2 K |
|
Solubility in water
|
soluble |
| Solubility |
soluble in ethanol
slightly soluble in ethyl ether |
| log P |
−0.123 |
| Acidity (pKa) |
10.25, 9.13 |
|
Refractive index (nD)
|
1.458 |
| Hazards |
| GHS pictograms |
|
| GHS signal word |
DANGER |
|
GHS hazard statements
|
H314 |
|
GHS precautionary statements
|
P280, P305+351+338, P310 |
| NFPA 704 |
|
| Flash point |
62 °C (144 °F; 335 K) |
| Lethal dose or concentration (LD, LC): |
|
LD50 (median dose)
|
2000 mg/kg (oral, rat) |
| Related compounds |
|
Related alkanamines
|
- n-Butylamine
- sec-Butylamine
- Putrescine
- Pentylamine
- Methylhexanamine
- Hexamethylenediamine
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
| Y verify (what is YN ?) |
| Infobox references |
|
|
Cadaverine is a foul-smelling diamine compound produced by the putrefaction of animal tissue. Cadaverine is a toxic[1] diamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine.
Contents
- 1 History
- 2 Production
- 3 Clinical significance
- 4 Toxicity
- 5 See also
- 6 References
- 7 External links
History
Putrescine[2] and cadaverine[3] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[4]
Production
Cadaverine is the decarboxylation product of the amino acid lysine.[5] This can be done by heating lysine with a small amount of Sodium bicarbonate mixed in. The produced gas should be led to a glass container which is surrounded by ice water. The heating must be done in a glass container, as metals may contaminate the process.
However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by living beings. It is partially responsible for the distinctive odors of urine.[6]
Clinical significance
Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. The odor commonly associated with bacterial vaginosis has been linked to cadaverine and putrescine.[7]
- Pentolinium & Pentamethonium are both chemical derivatives of cadaverine.
Toxicity
Cadaverine is toxic in large doses. In rats it has a low acute oral toxicity of 2000 mg/kg body weight, with no-observed-adverse-effect level of 2000 ppm (180 mg/kg body weight/day).[8]
See also
References
- ^ Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 212. ISBN 1-56670-223-2.
- ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.
- ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39. From page 39: Ich nenne das neue Diamin C5H16N2: "Cadaverin", da ausser der empirischen Zussamsetzung, welche die neue Base als ein Hydrür des Neuridins für den flüchtigen Blick erscheinen lässt, keine Anhaltspunkte für die Berechtigung dieser Auffassung zu erheben waren. (I call the new di-amine, C5H16N2, "cadaverine," since besides its empirical composition, which allows the new base to appear superficially as a hydride of neuridine, no clues for the justification of this view arose.)
- ^ Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
- ^ Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN 978-3-8348-1245-2.
- ^ Cadaverine PubChem
- ^ 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. PMC 3566083 . PMID 23405259. doi:10.1371/journal.pone.0056111.
- ^ Til, H.P.; Falke, H.E.; Prinsen, M.K.; Willems, M.I. (1997). "Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats". Food and Chemical Toxicology. 35 (3-4): 337–348. ISSN 0278-6915. doi:10.1016/S0278-6915(97)00121-X.
External links
|
Amino acid metabolism metabolic intermediates
|
| K→acetyl-CoA |
|
lysine→
|
- Saccharopine
- Allysine
- α-Aminoadipic acid
- α-Ketoadipate
- Glutaryl-CoA
- Glutaconyl-CoA
- Crotonyl-CoA
- β-Hydroxybutyryl-CoA
|
|
leucine→
|
- α-Ketoisocaproic acid
- β-hydroxy β-methylbutyric acid
- β-hydroxy β-methylbutyryl-CoA
- Isovaleryl-CoA
- 3-Methylcrotonyl-CoA
- 3-Methylglutaconyl-CoA
- HMG-CoA
|
|
tryptophan→alanine→
|
- N'-Formylkynurenine
- Kynurenine
- Anthranilic acid
- 3-Hydroxykynurenine
- 3-Hydroxyanthranilic acid
- 2-Amino-3-carboxymuconic semialdehyde
- 2-Aminomuconic semialdehyde
- 2-Aminomuconic acid
- Glutaryl-CoA
|
|
| G |
|
G→pyruvate→citrate
|
|
glycine→serine→
|
- glycine→creatine: Glycocyamine
- Phosphocreatine
- Creatinine
|
|
|
G→glutamate→
α-ketoglutarate
|
|
histidine→
|
- Urocanic acid
- Imidazol-4-one-5-propionic acid
- Formiminoglutamic acid
- Glutamate-1-semialdehyde
|
|
proline→
|
- 1-Pyrroline-5-carboxylic acid
|
|
arginine→
|
- Agmatine
- Ornithine
- Citrulline
- Cadaverine
- Putrescine
|
|
other
|
- cysteine+glutamate→glutathione: γ-Glutamylcysteine
|
|
|
G→propionyl-CoA→
succinyl-CoA
|
|
valine→
|
- α-Ketoisovaleric acid
- Isobutyryl-CoA
- Methacrylyl-CoA
- 3-Hydroxyisobutyryl-CoA
- 3-Hydroxyisobutyric acid
- 2-Methyl-3-oxopropanoic acid
|
|
isoleucine→
|
- 2,3-Dihydroxy-3-methylpentanoic acid
- 2-Methylbutyryl-CoA
- Tiglyl-CoA
- 2-Methylacetoacetyl-CoA
|
|
methionine→
|
- generation of homocysteine: S-Adenosyl methionine
- S-Adenosyl-L-homocysteine
- Homocysteine
- conversion to cysteine: Cystathionine
- alpha-Ketobutyric acid+Cysteine
|
|
threonine→
|
|
|
propionyl-CoA→
|
|
|
|
G→fumarate
|
|
phenylalanine→tyrosine→
|
- 4-Hydroxyphenylpyruvic acid
- Homogentisic acid
- 4-Maleylacetoacetic acid
|
|
|
G→oxaloacetate
|
|
|
| Other |
|
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Quality changes of salmon by-products during storage: Assessment and quantification by NMR.
- Shumilina E1, Slizyte R2, Mozuraityte R2, Dykyy A1, Stein TA1, Dikiy A3.
- Food chemistry.Food Chem.2016 Nov 15;211:803-11. doi: 10.1016/j.foodchem.2016.05.088. Epub 2016 May 14.
- Safe utilization of fish by-products is an important task due to increasing fish consumption. It can provide new valuable food/feed and will increase the economical profit and sustainability of the fishery industry. NMR spectroscopy is a reliable tool able to monitor qualitative and quantitative cha
- PMID 27283699
- Quality assurance of histamine analysis in fresh and canned fish.
- Evangelista WP1, Silva TM1, Guidi LR1, Tette PA1, Byrro RM1, Santiago-Silva P1, Fernandes C2, Gloria MB3.
- Food chemistry.Food Chem.2016 Nov 15;211:100-6. doi: 10.1016/j.foodchem.2016.05.035. Epub 2016 May 6.
- Histamine determination is relevant for fish safety, quality and trade. Recently a study by the European Union (EU) compared the Codex and the EU mandated methods for the analysis of histamine and observed that they underestimated and overestimated the results, respectively. To solve this problem, a
- PMID 27283612
- A new generation of smart amine donors for transaminase-mediated biotransformations.
- Gomm A1, Lewis W2, Green AP3, O'Reilly E4.
- Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2016 Jul 14. doi: 10.1002/chem.201603188. [Epub ahead of print]
- The application of ω-transaminase biocatalysts for the synthesis of optically pure chiral amines presents a number of challenges, including difficulties associated with displacing the challenging reaction equilibria. Herein, we report a highly effective approach using low equivalents of the novel d
- PMID 27411957
Japanese Journal
- New enzymatic methods for selective assay of L-lysine using an L-lysine specific decarboxylase/oxidase from Burkholderia sp. AIU 395(METHODS)
- Polyamines in Different Organs of Brassica Crop Plants with or without Clubroot Disease
- Free Amino Acids and Biogenic Amines Content during Ageing of Dry-cured Pork Loins Inoculated with Lactobacillus casei ŁOCK 0900 Probiotic Strain
Related Links
- cadaverineとは。意味や和訳。[名詞] 〔生化学〕 カダベリン C5H14N2. pentamethylenediamine ともいう. - 80万項目以上収録、例文・コロケーションが豊富な無料英和和英辞典。
- Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. However, this diamine is not purely associated with putrefaction. It is also ...