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| Diethyl maleate Basic information |
| Diethyl maleate Chemical Properties |
| Melting point | -10 °C (lit.) | | Boiling point | 225 °C (lit.) | | density | 1.064 g/mL at 25 °C (lit.) | | vapor density | 5.93 (vs air) | | vapor pressure | 1 mm Hg ( 14 °C) | | refractive index | n20/D 1.441(lit.) | | Fp | 200 °F | | storage temp. | Sealed in dry,Room Temperature | | solubility | 14mg/l | | form | Liquid | | color | Clear | | Water Solubility | insoluble | | Merck | 14,3123 | | BRN | 1100825 | | Stability: | Stable. Combustible. Incompatible with oxidizing agents, bases, acids, reducing agents. | | InChIKey | IEPRKVQEAMIZSS-AATRIKPKSA-N | | LogP | 2.2 | | CAS DataBase Reference | 141-05-9(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Butenedioic acid (Z)-, diethyl ester(141-05-9) | | EPA Substance Registry System | 2-Butenedioic acid (2Z)-, 1,4-diethyl ester (141-05-9) |
| Hazard Codes | Xi | | Risk Statements | 36-43-52/53 | | Safety Statements | 26-36/37-37-24-24/25 | | RIDADR | 3334 | | WGK Germany | 2 | | RTECS | ON1225000 | | Autoignition Temperature | 662 °F | | TSCA | Yes | | HS Code | 29171990 | | Toxicity | LD50 orally in rats: 0.30 g/kg (Smyth) |
| Diethyl maleate Usage And Synthesis |
| Chemical Properties | Diethyl maleate is a colorless clear liquid between the temperatures of -10°C (pour point) and 225°C (boiling point). Insoluble in water, soluble in ethanol and ether. its odor type is fruity and its odor at 100% is described as "fruity bananacitrus". It is prohibited by lFRA and theEU because of sensitization and is notused anymore as fragrance. | | Occurrence | Has apparently not been reported to occur in nature. | | Uses | Diethyl maleate can be used for the preparation of organophosphorus insecticide malathion. It is unsaturated polyester resins that are used in applications, such as reinforced glass fiber for boats, piping, bathtubs, roof panels, etc., and as protective coatings, finishes, and lacquers. | | Uses | Diethyl Maleate is used as a reagent in the synthesis of several organic compounds including that of polyaspartic acid ester based polyurea coatings. It was found to inhibit MCA and TPA transformed cell growth via modulation of glutathione, mitogen-activated protein kinase and cancer pathways. | | Definition | ChEBI: Diethyl maleate is a maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10℃) with boiling point 220℃ at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis. It has a role as a glutathione depleting agent. It is a maleate ester and an ethyl ester. It derives from an ethanol. | | Preparation | Diethyl maleate is synthesized by the direct esterification of maleic anhydride and ethanol in the presence of sulfuric acid. Esterification is a commonly used reaction in organic synthesis. | | General Description | Diethyl maleate is reported to occur in the cabernet sauvignon wine. | | Metabolism | α/β-Unsaturated compounds, such as diethyl maleate, react enzymically with gluta thione. The reaction has been demonstrated in fractions of rat liver (Boyland & Chasseaud, 1967) and avian liver (Wit & Snel, 1968). The enzyme differs from other known S-alkyl, S-aryl and S- epoxide transferase enzymes responsible for glutathione-conjugate formation (Boyland & Chasseaud, 1967). Diethyl maleate, administered parenterally to rats, reduced the hepatic glutathione content (Boyland & Chasseaud, 1970; Varga, Fischer & Szily, 1974). The latter workers also showed that diethyl maleate pretreatment of rats inhibited the glutathione conjugation of subsequently-adminis tered bromsulphthalein. |
| Diethyl maleate Preparation Products And Raw materials |
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