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120685

Sigma-Aldrich

N-Cyclohexylformamide

99%

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About This Item

Linear Formula:
HCONHC6H11
CAS Number:
766-93-8
Molecular Weight:
127.18
MDL number:
MFCD00003828
UNSPSC Code:
12352100
PubChem Substance ID:
24847425
NACRES:
NA.22

Quality Level

100

Assay

99%

form

solid

bp

113 °C/700 mmHg (lit.)

mp

36-41 °C (lit.)

SMILES string

O=CNC1CCCCC1

InChI

1S/C7H13NO/c9-6-8-7-4-2-1-3-5-7/h6-7H,1-5H2,(H,8,9)

InChI key

SWGXDLRCJNEEGZ-UHFFFAOYSA-N

Gene Information

human ... ADH1A(124) , ADH1B(125) , ADH1C(126) , ADH4(127) , ADH7(131) , EPHX2(2053)
mouse ... Ephx2(13850)

General description

N-Cyclohexylformamide binds to the complex of horse liver alcohol dehydrogenase with NADH and is similar to the Michaelis complex for aldehyde reduction catalyzed by the enzyme. It is formed during hydration of cyclohexyl isocyanide catalyzed by a novel enzyme isonitrile hydratase from Pseudomonas putida N19-2 .

Application

N-Cyclohexylformamide was used in the synthesis of 2-methylidene-1,3-selenazolidine derivatives.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Precautionary Statements

P261 - P280 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

>235.4 °F - closed cup

Flash Point(C)

> 113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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H Deng et al.
Biochemistry, 37(40), 14267-14278 (1998-10-07)
The binding of N-cyclohexylformamide (CXF) to the complex of horse liver alcohol dehydrogenase with NADH mimics that of the Michaelis complex for aldehyde reduction catalyzed by the enzyme. The Raman spectra of bound CXF and its 13C- and 15N-substituted derivatives
M Goda et al.
The Journal of biological chemistry, 276(26), 23480-23485 (2001-04-18)
Isonitrile containing an N triple bond C triple bond was degraded by microorganism sp. N19-2, which was isolated from soil through a 2-month acclimatization culture in the presence of this compound. The isonitrile-degrading microorganism was identified as Pseudomonas putida. The
Selenium-containing heterocycles from isoselenocyanates: synthesis of 2-methylidene-1, 3-selenazolidine derivatives.
Sommen GL, et al.
Tetrahedron, 62(14), 3344-3354 (2006)
S Ramaswamy et al.
Biochemistry, 36(12), 3522-3527 (1997-03-25)
Amides are analogs of aldehydes and potent inhibitors of liver alcohol dehydrogenases. They can be used for structural studies and for inhibiting the metabolism of alcohols that form toxic products. We studied N-alkyl amides that bind to the enzyme-NADH complex
S Svensson et al.
Journal of molecular biology, 302(2), 441-453 (2000-09-06)
The structure of mouse class II alcohol dehydrogenase (ADH2) has been determined in a binary complex with the coenzyme NADH and in a ternary complex with both NADH and the inhibitor N-cyclohexylformamide to 2.2 A and 2.1 A resolution, respectively.
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