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Diethyl pyrocarbonate

Diethyl pyrocarbonate (DEPC), also known as diethyl dicarbonate, is an organic compound with the molecular formula C₆H₁₀O₅ that serves as the diethyl ester of dicarbonic acid.^[1] It appears as a colorless liquid with a density of 1.101 g/mL at 25°C and a boiling point of 93–94°C at 18 mmHg, decomposing at 155°C into ethanol and carbon dioxide.^[2] Sensitive to moisture and pH changes, DEPC is widely used in molecular biology to inactivate ribonuclease (RNase) enzymes and was formerly employed as a preservative in beverages such as wines, soft drinks, and fruit juices (banned by the FDA in 1972 and prohibited in the EU due to urethane formation), where it hydrolyzes into non-toxic products.^[3]^[1]^[4]^[5] In laboratory settings, DEPC's primary application is the preparation of nuclease-free solutions for RNA handling, achieved by adding 0.1% (v/v) DEPC to deionized water or buffers, followed by autoclaving to remove residual reagent through decomposition into ethanol and CO₂.^[2] This treatment effectively inhibits RNases by carbethoxylating histidine residues in their active sites, preventing RNA degradation during experiments like PCR, dot blot hybridization, and RNA purification.^[3] Beyond RNase inhibition, DEPC acts as a covalent labeling agent in protein structural analysis, selectively modifying histidine and tyrosine residues to probe higher-order structures, protein-protein interactions, and conformational changes via mass spectrometry.^[2] It also serves as a chemical probe for nucleic acid structures, reacting with purine bases (e.g., adenine N-7 and N-6 positions) to detect distortions like Z-DNA or A-tracts in double-stranded DNA.^[3] Chemically, DEPC functions as a gentle esterifying agent in organic synthesis and has been used historically for peptide preservation through cross-linking.^[2] In the food industry, it was formerly used as a preservative, stemming from slow decomposition in aqueous environments containing amino acids, yielding ethanol and carbon dioxide without leaving harmful residues, but banned in the US (1972) and EU due to regulatory concerns over potential urethane formation, a carcinogen.^[1]^[4]^[5] Safety considerations are critical: DEPC is classified as acutely toxic if ingested (Acute Tox. 4 Oral) and a skin/eye irritant, with a flash point of 69°C necessitating storage at 2–8°C in a cool, dry place and handling under fume hoods with appropriate personal protective equipment including gloves, eyewear, and respirators.^[2]

Chemical identity

Nomenclature and synonyms

Diethyl pyrocarbonate is the accepted common name for this compound, reflecting its structure as a pyrocarbonate ester.^[1] Its official IUPAC name is ethoxycarbonyl ethyl carbonate, also known systematically as diethyl dicarbonate.^[6] Common synonyms include DEPC, DEP, diethyl oxydiformate, and Baycovin, with DEPC being particularly prevalent in biochemical and industrial contexts.^[1] The compound is assigned the CAS Registry Number 1609-47-8.^[6] As a member of the pyrocarbonic acid ester family, diethyl pyrocarbonate is the ethyl homolog of dimethyl pyrocarbonate, differing in the alkyl chain length of the ester groups.^[7]

Molecular formula and structure

Diethyl pyrocarbonate has the molecular formula C₆H₁₀O₅ and a molecular weight of 162.14 g/mol. The compound's structural formula is (C₂H₅O–C(O)–O–)₂O, depicting it as ethoxyformic anhydride, a mixed anhydride derived from carbonic acid. This structure relates to its naming as a pyrocarbonate, reflecting the diethyl ester of pyrocarbonic acid (dicarbonic acid), the formal anhydride of two carbonic acid molecules. The canonical SMILES notation is CCOC(=O)OC(=O)OCC.

Physical and chemical properties

Physical properties

Diethyl pyrocarbonate is a clear, colorless liquid at room temperature.^[8]^[9] Its density is 1.101 g/mL at 25 °C and 1.121 g/mL at 20 °C.^[8]^[10] The boiling point is 93–94 °C at 24 hPa (18 mmHg).^[8]^[10] As a liquid under standard conditions, it has no distinct melting point.^[8] The flash point is 69 °C (closed cup).^[8] It exhibits a refractive index of 1.398 (n²⁰_D).^[8]^[10] The dynamic viscosity is 1.97 mPa·s at 20 °C.^[11]^[12] Diethyl pyrocarbonate is soluble in ethanol and ether, with limited solubility in water (approximately 0.1 g/100 mL) owing to its instability in aqueous environments.^[8]^[10]

Chemical reactivity and stability

Diethyl pyrocarbonate (DEPC) undergoes hydrolysis in aqueous environments, decomposing to ethanol and carbon dioxide. The reaction proceeds via nucleophilic attack on the carbonyl groups, with the overall stoichiometry given by:

(\ce{EtOCO})_2\ce{O} + \ce{H2O} -> 2 \ce{EtOH} + 2 \ce{CO2}

This process is accelerated by the presence of nucleophiles, which facilitate the breakdown by enhancing the electrophilic character of the central oxygen atom.^[13]^[14] DEPC exhibits high reactivity toward nucleophilic sites, particularly through carbethoxylation, where it transfers an ethoxycarbonyl group to amines, including the imidazole ring of histidines and other protein residues such as lysines and tyrosines. This modification involves nucleophilic addition to the carbonyl, leading to stable carbamate derivatives. The compound's electrophilic nature, stemming from its pyrocarbonate structure, enables selective interactions with nucleophilic heteroatoms in biological molecules.^[14]^[15] Thermally, DEPC is unstable above 155 °C, decomposing to ethanol and carbon dioxide under heating conditions. This thermal instability limits its use in high-temperature processes and underscores the need for controlled storage below room temperature.^[13] DEPC shows pronounced sensitivity to pH and moisture, with rapid decomposition in basic or aqueous conditions; for instance, its half-life in phosphate buffer at 25 °C is 4 minutes at pH 6 and 9 minutes at pH 7.4, shortening further under alkaline conditions due to increased nucleophilic activity. Moisture alone triggers slow hydrolysis, generating pressure from CO₂ evolution.^[13]^[16] In terms of buffer compatibility, DEPC is incompatible with amine-containing buffers like Tris and HEPES, which accelerate hydrolysis through nucleophilic reaction; however, it remains stable in non-amine buffers such as phosphate or MOPS, allowing its use in those systems without significant degradation.^[13]^[17]^[18]

Synthesis

Laboratory preparation

Diethyl pyrocarbonate is commonly prepared in the laboratory by reacting ethyl chloroformate with sodium ethyl carbonate, which is generated in situ from sodium ethoxide and carbon dioxide under an inert atmosphere to prevent hydrolysis by moisture.^[19] Sodium ethoxide is first prepared by dissolving sodium metal in anhydrous ethanol, followed by bubbling dry carbon dioxide through the solution at room temperature to form the sodium ethyl carbonate intermediate.^[20] The subsequent addition of ethyl chloroformate to this intermediate proceeds as follows: \ce{NaO(CO)OEt + ClCO2Et -> (EtOCO)2O + NaCl} This reaction is typically conducted at low temperatures, between -10°C and 0°C, to minimize side reactions and decomposition, with stirring under nitrogen or argon.^[21] After the reaction, the mixture is filtered to remove the precipitated sodium chloride, and the crude product is dried over a dehydrating agent such as magnesium sulfate. Purification is achieved by distillation under reduced pressure (e.g., boiling point 83–84°C at 11 mm Hg) to isolate the clear, colorless to light yellow liquid, avoiding higher temperatures that could lead to thermal decomposition into ethanol and carbon dioxide. Typical yields range from 70% to 80%.^[21]^[19]

Industrial production

Diethyl pyrocarbonate is commercially manufactured via the reaction of phosgene with ethanol, summarized by the equation COCl₂ + 2 EtOH → (EtOCO)₂O + 2 HCl. This process proceeds through the intermediate formation of ethyl chloroformate (EtOCOCl) from phosgene and ethanol, followed by condensation of the chloroformate, often with aqueous sodium hydroxide (35–50% concentration) in the presence of a catalytic amount (0.1–1.0 mol%) of a phase-transfer catalyst such as bis[poly(oxy(C₂–C₄)alkylene)] C₆–C₂₀ aliphatic amine (e.g., PEG-15 stearamine). The reaction is conducted at low temperatures (0–20°C, preferably 5–10°C) to control exothermicity and ensure selectivity, typically in a solvent-free system to reduce environmental impact.^[22]^[23] Given phosgene's extreme toxicity and corrosivity, industrial production incorporates closed-loop systems for its handling and generation to prevent leaks and exposure, along with integrated neutralization of byproducts such as hydrogen chloride using bases like sodium hydroxide. These measures comply with rigorous safety protocols, including automated monitoring and containment to mitigate risks during the exothermic steps.^[24]^[23] Yields in this process reach up to 85–98%, depending on the specific variant, with final purification via vacuum distillation to achieve greater than 97% purity, aligning with commercial standards for laboratory and pharmaceutical applications. Historical developments have emphasized solvent-free and catalyst-optimized methods to improve efficiency and reduce waste, evolving from earlier solvent-based approaches.^[23]^[25]^[6] Due to its susceptibility to hydrolysis, diethyl pyrocarbonate produced industrially is handled and stored under anhydrous conditions to maintain stability. Cost factors are primarily influenced by the availability and price fluctuations of precursor ethanol, derived from renewable sources, and phosgene, which requires careful supply chain management owing to its regulated status.^[6]

Applications

In molecular biology

Diethyl pyrocarbonate (DEPC) is widely employed in molecular biology to inactivate ribonucleases (RNases), thereby preventing RNA degradation during experimental procedures. Its primary role involves the covalent modification of essential histidine residues in the active sites of RNases, such as RNases A, B, and C, which disrupts their catalytic activity and renders them inactive. This histidine-specific alkylation ensures irreversible inhibition, making DEPC a reliable tool for maintaining RNA integrity in sensitive assays.^[26]^[27] A standard protocol for preparing RNase-free solutions entails treating water or buffers with 0.1% v/v DEPC, followed by incubation for approximately 2 hours at 37 °C to allow sufficient reaction time for RNase inactivation. Subsequent autoclaving for 15 minutes is critical to hydrolyze residual DEPC into carbon dioxide and ethanol, eliminating any unreacted compound. This treatment is also applied to glassware by soaking in 0.1% DEPC overnight at 37 °C before autoclaving or baking, ensuring contamination-free surfaces for RNA handling.^[17]^[26] In practice, DEPC-treated solutions are integral to RNA extraction protocols, where they form the basis for lysis buffers and elution steps to protect isolated RNA from degradation. Similarly, DEPC is used in preparing PCR buffers and reaction mixes to safeguard RNA templates or cDNA during amplification, minimizing false negatives due to nuclease activity. These applications extend to routine lab preparations, such as DEPC-treated water stocks, which serve as a foundational reagent for diluting RNA samples and reagents in downstream analyses like Northern blotting or RT-qPCR.^[28]^[29] Despite its efficacy, DEPC has limitations, as residual unhydrolyzed DEPC can react with nucleic acids or inhibit enzymes such as reverse transcriptase and Taq polymerase, potentially compromising assay performance. Autoclaving is thus essential for complete removal, though over-treatment or incomplete hydrolysis may still introduce artifacts in enzyme-dependent reactions. In post-2012 molecular biology workflows, DEPC treatment remains a standard for custom RNase-free solutions, even as commercial RNase-free kits (e.g., from Thermo Fisher or QIAGEN) provide pre-treated reagents; however, DEPC is preferred for in-house preparations due to its cost-effectiveness and reliability in diverse protocols.^[3]^[17]^[30]

In protein modification and chemical research

Diethyl pyrocarbonate (DEPC) serves as a key reagent in protein modification studies, particularly for targeting the imidazole ring of histidine residues under mildly acidic to neutral conditions. At pH 6-7, DEPC selectively carbethoxylates the unprotonated nitrogen of the imidazole side chain, forming an N-carbethoxyhistidine adduct that disrupts protein function and enables site-specific probing.^[31] The reaction proceeds as follows:

\text{His} + (\ce{EtOCO})_2\text{O} \rightarrow \text{His-CO}_2\text{Et} + \text{EtOH} + \text{CO}_2

This modification is particularly useful for identifying catalytically important histidines in enzyme active sites, as demonstrated in early studies on ribonuclease where DEPC inactivation revealed essential histidine involvement in catalysis. Under controlled conditions, DEPC can also modify other nucleophilic residues such as lysine (via ε-amino groups), cysteine (thiol), and tyrosine (phenolic hydroxyl), though these reactions typically require higher pH or concentrations and are less specific than histidine carbethoxylation.^[32] The histidine modification by DEPC is reversible, allowing for controlled experiments in chemical research. Treatment of the carbethoxylated protein with 0.5 M hydroxylamine at pH 7.2 hydrolyzes the ethoxycarbonyl group, restoring the native histidine and enzyme activity, which confirms the specificity of the modification.86123-9/fulltext) This reversibility has been exploited in probing active sites of various enzymes, such as the Rieske iron-sulfur protein, where DEPC modification of ligating histidine 154 reduced the [2Fe-2S] cluster potential, highlighting its role in electron transfer.^[33] Beyond proteins, DEPC facilitates structural probing of DNA by carbethoxylating the N7 positions of adenine and guanine, which are more accessible in non-B-form conformations like cruciforms or Z-DNA. This reaction enhances reactivity in distorted regions, enabling footprinting analysis with single-nucleotide resolution, as shown in studies of negatively supercoiled plasmids. Modification progress is commonly monitored by UV spectroscopy, where carbethoxylation produces a characteristic absorbance increase at 240 nm (extinction coefficient ≈ 3200 M⁻¹ cm⁻¹), allowing quantification of modified residues without disrupting the sample.55762-3/pdf)

Other uses

Diethyl pyrocarbonate (DEPC) was historically employed as an antimicrobial preservative in beverages such as wine, soft drinks, and fruit juices during the 1960s and 1970s to inhibit microbial growth.^[34] Studies in 1971 revealed that DEPC decomposes to form urethane (ethyl carbamate), a known carcinogen, in treated beverages at concentrations up to 0.2 mg/L in orange juice.^[34] As a result, the U.S. Food and Drug Administration banned its use in food and beverages in 1972 due to the cancer risk.^[5]^[35] In organic synthesis, DEPC serves as a protecting agent for amino groups during peptide synthesis by forming carbamate derivatives that can be selectively removed.^[36] It also acts as a precursor for the preparation of β-ketoesters through reaction with active methylene compounds.^[36] As of 2025, DEPC finds limited application as an intermediate in pharmaceutical synthesis for producing organic compounds via its reactive pyrocarbonate group, though its use remains niche due to safety concerns.^[37] In discontinued research contexts, DEPC was used in early studies from the 1980s to probe enzyme inhibition mechanisms, such as binding to RNA polymerase and modifying histidine residues essential for activity in Escherichia coli.^[38]

Safety and regulatory aspects

Toxicity and health hazards

Diethyl pyrocarbonate (DEPC) exhibits acute toxicity primarily through oral and inhalation routes, with an oral LD50 in rats of 850 mg/kg, classifying it as harmful if swallowed under GHS category 4 (H302).^[12] It is also harmful if inhaled (GHS H332), with vapors causing respiratory tract irritation at high concentrations. Chronic exposure to DEPC shows limited evidence of carcinogenic potential, attributed to its in vivo decomposition into urethane (ethyl carbamate), a known carcinogen, particularly in the presence of ammonia or biological amines.^[39] Animal studies have demonstrated pulmonary tumors in mice treated with DEPC and ammonia, though DEPC alone does not exhibit strong carcinogenic activity.^[40] DEPC has not been classified by the International Agency for Research on Cancer (IARC) with respect to its carcinogenicity to humans. Additionally, DEPC acts as an irritant to skin (GHS H315), eyes (GHS H319), and the respiratory system (GHS H335).^[41] The primary toxicity mechanisms involve carbethoxylation of nucleophilic sites, such as histidine, lysine, cysteine, and tyrosine residues in proteins, leading to functional disruptions, and ethoxycarbonylation of purine bases (e.g., at N-7 of adenine and guanine) in DNA.^[3] Hydrolysis products of DEPC, including ethanol and carbon dioxide, pose low toxicity risk compared to the parent compound.^[42] Exposure primarily occurs via inhalation of vapors or skin absorption, resulting in symptoms such as eye and skin irritation, respiratory distress, nausea, and central nervous system depression at elevated levels.^[43]

Handling precautions and environmental impact

Diethyl pyrocarbonate (DEPC) should be stored in a cool, dry place at 2-8°C under an inert atmosphere such as argon, in tightly sealed glass containers to prevent moisture ingress and pressure buildup from hydrolysis; plastic containers should be avoided due to potential reactivity.^[44] Handling requires the use of appropriate personal protective equipment (PPE), including nitrile or butyl rubber gloves, safety goggles, and protective clothing, with all operations conducted in a well-ventilated fume hood to minimize vapor exposure and prevent accumulation.^[44]^[45] In the event of a spill, the area should be evacuated, ignition sources removed, and adequate ventilation ensured before containing the liquid with an inert absorbent material such as vermiculite or sand; the absorbed material is then transferred to a suitable container for disposal, and any residues neutralized with a mild base like sodium bicarbonate if necessary before cleanup.^[44]^[45] DEPC waste and DEPC-treated materials, such as laboratory solutions, are typically disposed of by incineration at an approved facility or, for biological waste, by autoclaving to inactivate residual DEPC prior to standard disposal protocols.^[44]^[46] Environmentally, DEPC exhibits low persistence owing to its rapid hydrolysis in aqueous environments, breaking down into ethanol and carbon dioxide, which aids in its natural degradation.^[44] It shows minimal bioaccumulation potential due to this hydrolysis and the small size of its degradation products, with no significant tendency to concentrate in organisms.^[42] In wastewater treatment, the ethanol byproduct is readily biodegradable through conventional microbial processes, facilitating effective removal without long-term ecological buildup.^[42] DEPC is listed on the EU EINECS inventory (EC 216-542-8) under REACH as a pre-registered substance, though full registration is not required due to low production volumes (<1 tonne/year); handlers must comply with general chemical safety assessments.^[47] In the US, OSHA does not establish specific permissible exposure limits for DEPC vapors, relying instead on general ventilation requirements and engineering controls to maintain exposure below hazardous levels.^[44]

References

[1]
Diethyl Pyrocarbonate | C6H10O5 | CID 3051 - PubChem - NIH
Diethyl pyrocarbonate is the diethyl ester of dicarbonic acid. It is functionally related to a dicarbonic acid. Preservative for wines, soft drinks, and fruit ...
[2]
Diethyl pyrocarbonate DEPC
### Diethyl Pyrocarbonate (DEPC) Product Information
[3]
Diethyl Pyrocarbonate - an overview | ScienceDirect Topics
DEPC is a potent, non-specific chemical inhibitor of RNase 2 and its most common application has been to make water nuclease-free.
[4]
https://www.law.cornell.edu/cfr/text/21/189.140
[5]
Dimethyl dicarbonate | C4H6O5 | CID 3086 - PubChem - NIH
Dimethyl dicarbonate | C4H6O5 | CID 3086 - structure, chemical names, physical and chemical properties, classification, patents, literature, ...
[6]
Diethyl pyrocarbonate 97 1609-47-8
### Physical Properties of Diethyl Pyrocarbonate
[7]
Diethyl pyrocarbonate, 97%, pure 5 g | Contact Us | thermofisher.com
6–10 day deliveryChemical Identifiers ; CAS1609-47-8 ; IUPAC Namediethyl dicarbonate ; Molecular FormulaC6H10O5 ; InChI KeyFFYPMLJYZAEMQB-UHFFFAOYSA-N.Missing: synonyms | Show results with:synonyms
[8]
Diethyl pyrocarbonate | 1609-47-8 - ChemicalBook
Gentle esterifying agent. Preservative for wines, soft drinks, fruit juices. Definition. ChEBI: The diethyl ester of dicarbonic acid. General Description.
[9]
Diethyl pyrocarbonate, 97%, pure 5 g | Thermo Scientific Chemicals
Viscosity, 1.97 mPa.s (20°C). Formula Weight, 162.14. Percent Purity, 97%. Grade, Pure. Chemical Name or Material, Diethyl pyrocarbonate. Show More Show Less ...
[10]
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2300384.htm
[11]
None
### Summary of Diethyl Pyrocarbonate (DEPC) Properties
[12]
[PDF] Reaction of Diethyl Pyrocarbonate with Nucleophiles
Kivinen 14 con- cluded that the neutral hydrolysis of diethyl pyrocarbonate in water takes place by a general base-catalyzed mechanism with water func-.<|separator|>
[13]
Covalent Labeling with Diethylpyrocarbonate is Sensitive to ... - NIH
Diethylpyrocarbonate (DEPC) is a simple to use, commercially-available covalent labeling reagent that can readily react with a range of nucleophilic residues ...
[14]
D7900 Diethylpyrocarbonate (DEPC) CAS: 1609-47-8
Appearance. Colorless, clear liquid ; Refractive Index (n20/D). 1.398 (lit.) ; Boiling Point. 93-94°C/18mmHg (lit.) ; Density. 1.101g/mL at 25°C (lit.) ; Molarity.
[15]
RNase and DEPC Treatment: Fact or Laboratory Myth - US
Autoclaving does inactivate DEPC by causing hydrolysis of diethylpyrocarbonate. CO2 and EtOH are released as reaction by-products. DEPC has a half-life of ...
[16]
Buffers for Biochemical Reactions - Promega Corporation
Examples of zwitterionic buffers include MOPS and HEPES; Tris and phosphate buffers do not isomerize into zwitterions. Minimal salt effects. In other words ...
[17]
US3984386A - Polymerization of ethylenically unsaturated ...
Thereafter, the sodium ethyl carbonate is reacted with ethyl chloroformate to form diethyl pyrocarbonate and sodium chloride. The chloride salt is filtered ...
[18]
Synthesis of diethyl pyrocarbonate - PrepChem.com
The dialkyl pyrocarbonates may be prepared by reacting alkali metal alkyl carbonate, eg, sodium ethyl carbonate, with alkyl halocarbonate, eg, ethyl ...Missing: laboratory | Show results with:laboratory
[19]
Diethyl pyrocarbonate synthesis - ChemicalBook
Synthesis of Diethyl pyrocarbonate from Ethyl chloroformate and Octadecanamine.Chemicalbook can provide 2 synthetic routes.Missing: laboratory | Show results with:laboratory
[20]
Method for preparing di(organo) esters of pyrocarbonic acid
This example describes the preparation of diethyl pyrocarbonate with PEG 15 stearamine as the catalyst. [0021]. A solution of ethyl chloroformate (114.2 grams ( ...Missing: ethoxide | Show results with:ethoxide
[21]
Diethyl pyrocarbonate 1609-47-8 wiki - Guidechem
Diethyl pyrocarbonate CAS 1609-47-8 WIKI information includes physical ... It is typically prepared through the reaction of phosgene with ethanol in a ...
[22]
https://www.guidechem.com/encyclopedia/diethyl-pyrocarbonate-dic9039.html
[23]
Phosgene - Chemical Safety Facts
Mar 1, 2023 · Phosgene is an important chemical intermediate used in the process to manufacture a variety of industrial and consumer products. Phosgene is ...
[24]
US3078294A - Process for making pyrocarbonate esters
Mixed pyrocarbonate esters may be prepared by our process by reacting phosgene with a mixture of two different carbonate half esters. By this procedure there is ...
[25]
https://patents.google.com/patent/US3078294A/en
[26]
Identification of functionally relevant histidine residues in the ... - NIH
Chemical modification with DEPC inactivates the enzyme, suggesting that histidine residues play a decisive role in the catalytic mechanism of this nuclease.
[27]
Precautions for Handling of RNA - Roche Life Science
All solutions, except Tris buffers, should be treated with 0.1% DEPC (or DMPC) overnight at room temperature and then autoclaved. Autoclaving hydrolyzes and ...
[28]
Working with RNA: Hints and Tips | Bioline | Meridian Bioscience
DEPC-treated water: Use DEPC-treated water instead of regular PCR grade water. DEPC inactivates RNase by histidine modification of the bases. If DEPC ...<|separator|>
[29]
Efficient and High-Quality RNA Isolation from Metabolite-Rich ... - NIH
Solutions and Reagents All glass apparatus, mortar and pestle, and plastic wares were pre-treated with 0.1% DEPC (diethylpyrocarbonate) overnight and then ...
[30]
Modification of system A amino acid carrier by diethyl pyrocarbonate.
Modification of system A amino acid carrier by diethyl pyrocarbonate. ... Histidine modification by DEPC can be reversed by hy- droxylamine under the ...
[31]
Modification of enoyl-CoA hydratase using diethyl pyrocarbonate
No tyrosine, cysteine or tryptophan residues are modified by diethyl pyrocarbonate. However, out of the 22 amino groups per subunit, 2–5 groups do react ...
[32]
Chemical Modification of the Rieske Protein from Thermus ...
Chemical Modification of the Rieske Protein from Thermus thermophilus Using Diethyl Pyrocarbonate Modifies Ligating Histidine 154 and Reduces the [2Fe-2S] ...Results · Discussion · Supporting Information · References
[33]
Diethyl pyrocarbonate: formation of urethan in treated beverages
Isotope dilution analyses with tritium-labeled diethyl pyrocarbonate show that the carcinogen urethan is formed in orange juice, white wine, and beer.Missing: (EtOCO) 2O<|control11|><|separator|>
[34]
[PDF] Nomination Background: Urethane (CASRN: 51-79-6)
(made from ethanol and phosgene) with ammonia (!ARC, 1974). The 1979 TSCA ... Therefore, in 1972, FDA banned the use of diethyl pyrocarbonate in beverages and ...
[35]
21 CFR Part 189 -- Substances Prohibited from Use in Human Food
The food ingredients listed in this section have been prohibited from use in human food by the Food and Drug Administration because of a determination that ...
[36]
The Multifaceted Applications of Diethyl Pyrocarbonate in Chemical ...
Oct 31, 2025 · Discover the diverse uses of Diethyl Pyrocarbonate (DEPC), from protein modification to its role as a key synthesis intermediate, ...
[37]
Chemical Modification of Escherichia Coli RNA Polymerase by ...
Chemical Modification of Escherichia Coli RNA Polymerase by Diethyl Pyrocarbonate: Evidence of Histidine Requirement for Enzyme Activity and Intrinsic Zinc ...Missing: spectroscopy | Show results with:spectroscopy
[38]
In vivo formation of a carcinogenic substance from diethyl ... - PubMed
In adult mice treated with DEPC plus ammonia, pulmonary tumours developed. However, DEPC or ammonia alone proved not to have any carcinogenic effect.Missing: mechanism | Show results with:mechanism
[39]
Possible in vivo formation of a carcinogenic substance from diethyl ...
The lung tumors may result from a carcinogenic substance, supposedly urethane, formed in vivo from diethyl pyrocarbonate in the presence of ammonia.Missing: mechanism | Show results with:mechanism
[40]
<h2>List of Classifications</h2>
- **Search Result**: Diethyl pyrocarbonate (CAS 1609-47-8) is not explicitly listed in the provided content from the IARC Monographs List of Classifications.
[41]
https://www.sigmaaldrich.com/sds/aldrich/40718
[42]
[PDF] Diethyl Pyrocarbonate - Santa Cruz Biotechnology
Diethyl dicarbonate slowly decomposes in aqueous solutions and in combination with amino acids and proteins found in beverages (for which it is a preservative) ...
[43]
[PDF] Material Safety Data Sheet - Diethyl pyrocarbonate - Cole-Parmer
May be harmful if swallowed. Inhalation: Causes respiratory tract irritation. Inhalation at high concentrations may cause CNS depression and asphixiation.
[44]
None
### Summary for Diethyl Pyrocarbonate (Aldrich - 40718)
[45]
[PDF] SAFETY DATA SHEET - Fisher Scientific
Sep 26, 2009 · Soluble in water Persistence is unlikely based on information available. Page 5 / 7. Page 6. Diethyl pyrocarbonate.
[46]
[PDF] Safety Data Sheet - G-Biosciences
Precautions for safe handling. : Ensure good ventilation of the work station ... diethyl pyrocarbonate (1609-47-8). No additional information available.
[47]
[PDF] Safety Data Sheet: Diethyl pyrocarbonate - Carl ROTH
Kinematic viscosity. 1,759 mm²/s at 20 °C. Dynamic viscosity. 1,97 mPa s at 20 °C. Solubility(ies). Water solubility. (slow decomposition). Partition ...