All Photos(1)

159220

Sigma-Aldrich

Diethyl pyrocarbonate

97%

Synonym(s):
Diethyl dicarbonate, DEPC, Diethyl oxydiformate, DEP, Ethoxyformic acid anhydride
Linear Formula:
O(COOC2H5)2
CAS Number:
Molecular Weight:
162.14
Beilstein:
637031
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

liquid

refractive index

n20/D 1.398 (lit.)

bp

93-94 °C/18 mmHg (lit.)

density

1.101 g/mL at 25 °C (lit.)

shipped in

wet ice

storage temp.

2-8°C

SMILES string

CCOC(=O)OC(=O)OCC

InChI

1S/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H3

InChI key

FFYPMLJYZAEMQB-UHFFFAOYSA-N

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General description

Diethyl pyrocarbonate reacts selectively with the single-stranded loops of cruciform structures. The irreversible inactivation of ribonuclease with diethylpyrocarbonate has been studied.

Application

Diethyl pyrocarbonate was used as:
  • nuclease inhibitor for the extraction of undegraded nucleic acids from etiolated and green plant tissues
  • an antimicrobial additive
  • ribonuclease inhibitor
  • histidine residue modifier
  • reagent for conversion of imines to carbamates
Modification reagent for His and Tyr residues in proteins. Robust probe for structural disruptions in dsDNA, reacting with fully or partially unstacked bases.

Packaging

5 g in glass bottle
25, 100 g in poly bottle

Biochem/physiol Actions

Inactivates RNase in solution at about 0.1% (v/v), thus protecting RNA against degradation.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

156.2 °F - closed cup

Flash Point(C)

69 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Isolation of plant RNA.
R Hodge
Methods in molecular biology (Clifton, N.J.), 28, 37-40 (1994-01-01)
A mechanism of the irreversible inactivation of bovine pancreatic ribonuclease by diethylpyrocarbonate. A general reaction of diethylpyrocarbonate . A general reaction of diethylpyrocarbonate with proteins.
B Wolf et al.
European journal of biochemistry, 13(3), 519-525 (1970-04-01)
Tetrahedron, 48, 3445-3445 (1992)
P D Pelton et al.
The Journal of biological chemistry, 267(9), 5916-5920 (1992-03-25)
The pH dependence of myo-inositol monophosphatase may indicate a role for histidine residues in the catalytic mechanism (Ganzhorn, A. J., and Chanal, M.-C. (1990) Biochemistry 29, 6065-6071). This possibility was investigated by chemical modification. At pH 6.0 and 25 degrees
J C Furlong et al.
Nucleic acids research, 14(10), 3995-4007 (1986-05-27)
Diethyl pyrocarbonate reacts with the single-stranded loops of cruciform structures with great selectivity. Adenine bases are carbethoxylated, as a result of which the backbone may be cleaved with piperidine, and the level of chemical modification at each base may be

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