Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/06/12 21:25:45」(JST)

wiki en

Semicarbazide is the chemical compound with the formula OC(NH₂)(N₂H₃). It is a water-soluble white solid. It is a derivative of urea.

Synthesis

The compound prepared by treating urea with hydrazine:^[1]

OC(NH₂)₂ + N₂H₄ → OC(NH₂)(N₂H₃) + NH₃

A further reaction can occur to give carbohydrazide:

OC(NH₂)(N₂H₃) + N₂H₄ → OC(N₂H₃)₂ + NH₃

Derivatives

Semicarbazide is frequently reacted with aldehydes and ketones to produce semicarbazones via a condensation reaction. This is an example of imine formation resulting from the reaction of a primary amine with a carbonyl group. The reaction is useful because semicarbazones, like oximes and 2,4-DNPs, typically have high melting points and crystallize, facilitating purification or identification of reaction products.^[2]

Thiosemicarbazide is the analogous compound with sulfur atom in place of oxygen atom,^[3] with 4-Methyl-3-thiosemicarbazide being a simple example.

Properties

Semicarbazide products (semicarbazones and thiosemicarbazones) are known to have an activity of antiviral, antiinfective and antineoplastic through binding to copper or iron in cells.

Uses

Semicarbazide is used in preparing pharmaceuticals including: nitrofuran antibacterials (furazolidone, nitrofurazone, nitrofurantoin) and dizatrifone.

Semicarbazide is used as a detection reagent in thin layer chromatography (TLC). Semicarbazide stains α-keto acids on the TLC plate, which must then be viewed under ultraviolet light to see the results.

Occurrence

Semicarbazide has been shown to be formed in heat-treated flour containing azodicarbonamide as well as breads made from azodicarbonamide-treated flour.^[4]

Structures

Urea
Hydrazine
Thiosemicarbazide

References

^ Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
^ John McMurry (1984). Organic Chemistry. Brooks/Cole. p. 676.
^ . PubChem https://pubchem.ncbi.nlm.nih.gov/compound/2723789. Missing or empty |title= (help)
^ Becalski, Adam; Lau, Benjamin; Lewis, David; Seaman, Stephen (2004). "Semicarbazide Formation in Azodicarbonamide-Treated Flour: A Model Study". J. Agric. Food Chem. 52 (18): 5730–4. PMID 15373416. doi:10.1021/jf0495385.

External links

Compounds Containing a N-CO-N-N or More Complex Group

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

English Journal

Novel 1-acyl-4-substituted semicarbazide derivatives of primaquine - synthesis, cytostatic, antiviral and antioxidative studies.

Perković I, Tršinar S, Zanetić J, Kralj M, Martin-Kleiner I, Balzarini J, Hadjipavlou-Litina D, Katsori AM, Zorc B.SourceFaculty of Pharmacy and Biochemistry, University of Zagreb , Zagreb , Croatia.
Journal of enzyme inhibition and medicinal chemistry.J Enzyme Inhib Med Chem.2013 Jun;28(3):601-10. doi: 10.3109/14756366.2012.663366. Epub 2012 Mar 1.
A series of novel 1,4-substituted semicarbazides 5a-g with a primaquine moiety bridged by a carbonyl group at position 1 and a cycloalkyl, aryl, benzyloxy or hydroxy substituent at position 4 were prepared and biologically evaluated. The synthetic pathways applied for preparation of the title compou
PMID 22380782

Rapid detection of economic adulterants in fresh milk by liquid chromatography-tandem mass spectrometry.

Abernethy G, Higgs K.SourceFonterra Research and Development Centre, Private Bag 11029, Palmerston North 4442, New Zealand. Electronic address: grant.abernethy@fonterra.com.
Journal of chromatography. A.J Chromatogr A.2013 May 3;1288:10-20. doi: 10.1016/j.chroma.2013.02.022. Epub 2013 Feb 16.
A method to aid in the detection of the economically driven adulteration of fresh milk with a range of small, nitrogen containing compounds, including melamine, ammeline, ammelide, cyanuric acid, allantoin, thiourea, urea, biuret, triuret, semicarbazide, aminotriazine, 3- and 4-aminotriazole, cyanam
PMID 23540766

Arterial vascular cell line expressing SSAO: a new tool to study the pathophysiology of vascular amine oxidases.

Ullah K, Xie B, Iqbal J, Rasool A, Qing H, Deng Y.SourceSchool of Life Science and Technology, Beijing Institute of Technology, Beijing, 100081, China.
Journal of neural transmission (Vienna, Austria : 1996).J Neural Transm.2013 Apr 2. [Epub ahead of print]
Semicarbazide-sensitive amine oxidase (SSAO) widely exists in nature, mainly expressed at significant levels in vasculature. It plays a detrimental role in vascular diseases, particularly atherosclerosis, which occurs mainly in arteries. Herein we for the first time present SSAO expression in arteri
PMID 23546801

Japanese Journal

Determination of human serum semicarbazide-sensitive amine oxidase activity via flow injection analysis with fluorescence detection after online derivatization of the enzymatically produced benzaldehyde with 1,2-diaminoanthraquinone

El-Maghrabey Mahmoud H.,Kishikawa Naoya,Ohyama Kaname,Imazato Takahiro,Ueki Yukitaka,Kuroda Naotaka
Analytica Chimica Acta 881, 139-147, 2015-06-30
… A fast, simple, and sensitive flow injection analysis method was developed for the measurement of semicarbazide-sensitive amine oxidase (SSAO) activity in human serum. …
NAID 120005617351

Benzofuran–Morpholinomethyl–Pyrazoline Hybrids as a New Class of Vasorelaxant Agents: Synthesis and Quantitative Structure–Activity Relationship Study

Hassan Ghaneya Sayed,Abdel Rahman Doaa Ezzat,Saleh Dalia Osama,Abdel Jaleel Gehad Abdel Raheem
Chemical and Pharmaceutical Bulletin 62(12), 1238-1251, 2014
… The benzofuran–morpholinomethyl–pyrazoline hybrids 4a–e, 5a–e and 6a–j were synthesized via reaction of α,β-unsaturated carbonyl compounds 3a–e with hydrazine hydrate, semicarbazide or thiosemicarbazide. …
NAID 130004712919

Purification and Molecular Analysis of a Monoamine Oxidase Isolated from Narcissus tazetta

CUI Zhifeng,ZHANG Yongming,INOUE Hironori [他],YOGO Syun,HIRASAWA Eiji
Bioscience, Biotechnology, and Biochemistry 77(8), 1728-1733, 2013
… Semicarbazide-sensitive amine oxidase activity was detected in Narcissus tazetta. …
NAID 130003361196

Related Pictures

★リンクテーブル★

拡張検索	「thiosemicarbazide」

「thiosemicarbazide」

Semicarbazide
Identifiers
CAS Number	57-56-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28306 ;
ChemSpider	5008 ;
ECHA InfoCard	100.000.308
KEGG	C02077 ;
PubChem CID	5196;
	InChI InChI=1S/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5) Key: DUIOPKIIICUYRZ-UHFFFAOYSA-N ; InChI=1/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5) Key: DUIOPKIIICUYRZ-UHFFFAOYAJ ;
	SMILES C(=O)(N)NN ;
Properties
Chemical formula	H2NNHC(=O)NH2
Molar mass	75.08 g/mol
Melting point	96 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

チオセミカルバジド

[Ullmann-1] Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.

[2] John McMurry (1984). Organic Chemistry. Brooks/Cole. p. 676.

[3] . PubChem https://pubchem.ncbi.nlm.nih.gov/compound/2723789. Missing or empty |title= (help)

[4] Becalski, Adam; Lau, Benjamin; Lewis, David; Seaman, Stephen (2004). "Semicarbazide Formation in Azodicarbonamide-Treated Flour: A Model Study". J. Agric. Food Chem. 52 (18): 5730–4. PMID 15373416. doi:10.1021/jf0495385.

匿名

検索

案内

案内

semicarbazide