Diethyl pyrocarbonate
[CAS# 1609-47-8]

Identification

• Classification: Organic raw materials >> Inorganic acid ester
• Name: Diethyl pyrocarbonate
• Synonyms: DEPC; Diethyl oxydiformate; Ethoxyformic anhydride; Pyrocarbonic acid diethyl ester
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• CAS Registry Number: 1609-47-8
• EC Number: 216-542-8
• SMILES: CCOC(=O)OC(=O)OCC

Properties

• Density: 1.101
• Boiling point: 93-94 °C (18 mmHg)
• Refractive index: 1.396-1.4
• Flash point: 69 °C
• Water solubility: slow decomposition

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	4	H332
Flammable liquids	Flam. Liq.	4	H227
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	3	H336
Acute toxicity	Acute Tox.	3	H311
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Diethyl pyrocarbonate (DEPC) is an organic chemical compound first synthesized in the mid-20th century and has since become a valuable reagent in biochemical research and industrial applications. It is a diester of pyrocarbonic acid and is commonly used as a potent agent for modifying biological molecules.

One of the primary applications of DEPC is in molecular biology, where it is utilized to modify nucleic acids and proteins. DEPC acts as a potent inactivator of ribonucleases (RNases), enzymes that degrade RNA. By reacting with the histidine residues of RNases, DEPC effectively deactivates these enzymes, which is crucial for the preservation of RNA samples in research laboratories. This application is particularly important during RNA extraction and purification processes, where the presence of active RNases can lead to the degradation of RNA, thereby compromising experimental results.

In addition to its role in molecular biology, DEPC is used in the chemical industry for various purposes. It serves as a reagent in the synthesis of other chemical compounds, particularly those involving esterification reactions. Its reactivity with alcohols and phenols makes it useful for creating esters and other derivatives, which are employed in the production of pharmaceuticals, agrochemicals, and specialty chemicals.

DEPC is also used as a cross-linking agent in the preparation of certain polymer materials. Its ability to form stable ester bonds allows for the modification of polymer structures, enhancing their properties and performance in specific applications. This feature makes DEPC valuable in the development of advanced materials with tailored characteristics.

Despite its usefulness, DEPC must be handled with care due to its potential health hazards. It is a toxic and irritant substance, requiring appropriate safety measures and protective equipment during its use. Research continues to focus on improving the safety protocols associated with DEPC and exploring alternative reagents with similar functionalities but reduced toxicity.

References

1979. Chemical modification of histidyl and lysyl residues in yeast enolase. Biochimica et Biophysica Acta (BBA) - Enzymology, 578(1), 1-9.
DOI: 10.1016/0005-2744(79)90081-0

1997. Basic Nucleic Acid Procedures. Molecular Diagnostics, 1, 29-45.
DOI: 10.1007/978-1-4757-2588-9_3

1991. Modification of system A amino acid carrier by diethyl pyrocarbonate. The Journal of Biological Chemistry, 266(2), 987-992.
DOI: 10.1016/s0021-9258(17)35243-2