Compound: diethyl pyrocarbonate
SMILES: O=C(OC(=O)OCC)OCC
InChIKey: FFYPMLJYZAEMQB-UHFFFAOYSA-N
Synonyms: diethyl pyrocarbonate, 1609-47-8, Diethyl dicarbonate, DEPC, Diethyl oxydiformate, Diethylpyrocarbonate, Baycovin, Ethyl pyrocarbonate, Piref, Dicarbonic acid, diethyl ester, Dicarbonic acid diethyl ester, Diethyl pyrocarbonic acid, Oxydiformic acid diethyl ester, Pyrocarbonic acid diethyl ester, Diethylpyrokarbonat, Ethoxyformic acid anhydride, Pyrocarbonate d'ethyle, Pyrokohlensaeure diaethyl ester, Diethylester kyseliny diuhlicite, Pyrocarbonic acid, diethyl ester, Diethyl ester of pyrocarbonic acid, Dicarbonate, Diethyl, Oxydiformate, Diethyl, Pyrocarbonate, Diethyl, Anhydride, Ethoxyformic, DTXSID2051764, LMR3LZG146, UE-5908, DTXCID1030319, CHEBI:59051, RefChem:133441, 216-542-8, Ethoxyformic Anhydride, ethoxycarbonyl ethyl carbonate, Dicarbonic acid, 1,3-diethyl ester, MFCD00009106, FORMIC ACID, OXYDI-, DIETHYL ESTER, CHEMBL55517, DKD, UNII-LMR3LZG146, Diethylpyrokarbonat [Czech], CCRIS 4920, Diethyldicarbonate, Pyrocarbonate d'ethyle [French], EINECS 216-542-8, BRN 0637031, Diethylester kyseliny diuhlicite [Czech], Pyrokohlensaeure diaethyl ester [German], Pyrocarbonate d''ethyle, ethoxycarbonyl ethoxyformate, Diethyl pyrocarbonate, 97%, SCHEMBL15582, 4-03-00-00018 (Beilstein Handbook Reference), orb1944980, DIETHYL PYROCARBONATE [MI], Diethyl pyrocarbonate, 99% (NT), HY-D0846, Tox21_303976, BDBM50035000, Dicarbonic acid, C,C'-diethyl ester, AKOS015900388, Diethyl pyrocarbonate, >=97% (NMR), EBC-612838, FD11913, carbonic acid, ethoxycarbonyl ethyl ester, NCGC00357200-01, AS-10585, DA-52522, CARBONIC ACID,ETHYL ESTER,ANHYDRIDE, CAS-1609-47-8, DICARBONIC ACID C,C'-DIETHYL ESTER, CS-0014816, NS00021720, ST51037226, EN300-84341, Diethyl pyrocarbonate, purum, >=97.0% (NT), H11295, F241133, Q421385, Diethyl pyrocarbonate, Vetec(TM) reagent grade, >=97%, Dicarbonic Acid, Diethyl Ester; Formic Acid, Oxydi-, Diethyl Ester;, InChI=1/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H
Theoretical properties:
molecular_formula: C6H10O5
molecular_weight: 162.14 g/mol
exact_mass: 162.05282342 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 6
heavy_atom_count: 11
topological_polar_surface_area: 61.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: < 25 °C
Descriptions:
{"pubchem": "Diethyl pyrocarbonate is the diethyl ester of dicarbonic acid. It is functionally related to a dicarbonic acid.", "chebi": "The diethyl ester of dicarbonic acid.", "chembl": "DIETHYL PYROCARBONATE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Diethyl pyrocarbonate (DEPC), also called diethyl dicarbonate (IUPAC name), is used in the laboratory to inactivate RNase enzymes in water and on laboratory utensils. It does so by the covalent modification of histidine (most strongly), lysine, cysteine, and tyrosine residues.\nDEPC-treated (and therefore RNase-free) water is used in handling of RNA in the laboratory to reduce the risk of RNA being degraded by RNases.\nWater is usually treated with 0.1% v/v DEPC for at least 2 hours at 37 \u00b0C and then autoclaved (at least 15 min) to inactivate traces of DEPC. Inactivation of DEPC in this manner yields CO2 and ethanol. Higher concentrations of DEPC are capable of deactivating larger amounts of RNase, but remaining traces or byproducts may inhibit further biochemical reactions such as in vitro transcription. Furthermore, chemical modification of RNA such as carboxymethylation is possible when traces of DEPC or its byproducts are present, resulting in impaired recovery of intact RNA even after buffer exchange (after precipitation).\n\nDEPC is unstable in water and susceptible to hydrolysis to carbon dioxide and ethanol, especially in the presence of a nucleophile. For this reason, DEPC cannot be used with Tris or HEPES buffers. In contrast, it can be used with phosphate-buffered saline or MOPS. A handy rule is that enzymes or chemicals which have active -O:, -N: or -S: cannot be treated with DEPC to become RNase-free, as DEPC reacts with these species. Furthermore, DEPC degradation products can inhibit in vitro transcription.\nDEPC derivatization of histidines is also used to study the importance of histidyl residues in enzymes.  Modification of histidine by DEPC results in carbethoxylated derivates at the N-omega-2 nitrogen of the imidazole ring.  DEPC modification of histidines can be reversed by treatment with 0.5 M hydroxylamine at neutral pH.\nDEPC can also be used for probing the structure of double-stranded DNA."}