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159220

Sigma-Aldrich

Diethyl pyrocarbonate

96% (NT)

Synonym(s):

DEP, DEPC, Diethyl dicarbonate, Diethyl oxydiformate, Ethoxyformic acid anhydride

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About This Item

Linear Formula:
O(COOC2H5)2
CAS Number:
Molecular Weight:
162.14
Beilstein:
637031
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form:
liquid
Assay:
96% (NT)
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Quality Level

Assay

96% (NT)

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.)

functional group

carbonate

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.[1] The irreversible inactivation of ribonuclease with diethylpyrocarbonate has been studied.[2]

Application

Diethyl pyrocarbonate was used as:
  • nuclease inhibitor for the extraction of undegraded nucleic acids from etiolated and green plant tissues[3]
  • an antimicrobial additive[4]
  • ribonuclease inhibitor[5]
  • histidine residue modifier[6]
  • reagent for conversion of imines to carbamates[7]
Modification reagent for His and Tyr residues in proteins. Robust probe for structural disruptions in dsDNA, reacting with fully or partially unstacked bases.

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

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Heather L Walsh et al.
PloS one, 15(8), e0236104-e0236104 (2020-08-11)
There is an increasing emphasis on effects-based monitoring to document responses associated with exposure to complex mixtures of chemicals, climate change, pathogens, parasites and other environmental stressors in fish populations. For decades aquatic monitoring programs have included the collection of
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)
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
Food Sci. Technol., 57, 343-343 (1993)

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Questions

  1. What is the solubility and solution stability of Diethyl pyrocarbonate, DEPC?

    1 answer
    1. DEPC can be solubilized in 95% ethanol, e.g. 1.6 mL in 4 mL ethanol gives a clear, colorless solution. DEPC is soluble in alcohols, esters, ketones and other hydrocarbons, but has limited solubility in water (~0.1%). 6 DEPC hydrolyzes in aqueous solution, to form ethanol and carbon dioxide (CO2). Typically a 0.1% DEPC solution (1 mL of DEPC diluted in water to 1 L) is used to inactivate RNase. The DEPC will not immediately dissolve, as evidenced by the appearance of globules. The mixture should be stirred until the globules disappear. DEPC is sensitive to pH. In phosphate buffer at 25 °C, its half-life is 4 minutes at pH 6, and 9 minutes at pH 7. Hydrolysis is accelerated by Tris buffer,7 where at 25 °C, the half-life of DEPC was reported to be 1.25 minutes at pH 7.5, and 0.37 minutes at pH 8.2. DEPC will decompose in solution when autoclaved. For 0.1% DEPC solutions, autoclaving for 15 minutes per liter should be sufficient.
      DEPC is very sensitive to moisture. As such, DEPC is packaged under argon to help reduce exposure to moisture. If DEPC is exposed to even traces of moisture, some hydrolysis occurs. The resulting CO2 is more soluble in DEPC solutions at 2–8 °C than at room temperature. As the product is brought to room temperature before opening, the DEPC can become supersaturated with respect to any dissolved gas. After opening the bottle for the first time and each time thereafter, layer nitrogen or argon gas over the DEPC and store the closed bottle at 2–8 °C for optimal stability. It may be helpful to store the bottle inside a sealed plastic bag with desiccant, but with the bottle cap slightly loose. If the bag inflates at all, this indicates some degree of decomposition with possible pressure build-up. Once opened, the bottle should not be kept for more than 9 months. DEPC decomposes at 155 °C. DEPC is also sensitive to ammonia, which causes decomposition to urethane.

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