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| | L(+)-Diethyl L-tartrate Basic information |
| | L(+)-Diethyl L-tartrate Chemical Properties |
| Melting point | 17 °C | | alpha | 7.5 º (neat) | | Boiling point | 280 °C (lit.) | | density | 1.204 g/mL at 25 °C (lit.) | | vapor pressure | 0.402Pa at 25℃ | | refractive index | n20/D 1.446(lit.) | | FEMA | 2378 | DIETHYL TARTRATE | | Fp | 200 °F | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Water (Slightly) | | pKa | 11.61±0.20(Predicted) | | form | Viscous Liquid | | color | Clear | | Odor | at 100.00 %. mild fruity wine caramellic | | Odor Type | fruity | | Optical Rotation | [α]20/D +8.5°, neat | | biological source | synthetic | | Water Solubility | insoluble | | Merck | 14,3855 | | JECFA Number | 622 | | BRN | 1727145 | | Dielectric constant | 4.5（20℃） | | Major Application | flavors and fragrances | | InChI | 1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m1/s1 | | InChIKey | YSAVZVORKRDODB-PHDIDXHHSA-N | | SMILES | CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC | | LogP | 0.2 at 25℃ | | CAS DataBase Reference | 87-91-2(CAS DataBase Reference) | | NIST Chemistry Reference | Diethyl tartrate(87-91-2) | | EPA Substance Registry System | Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, 1,4-diethyl ester (87-91-2) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 24/25-36-26 | | WGK Germany | 3 | | TSCA | TSCA listed | | HS Code | 29181300 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2 |
| | L(+)-Diethyl L-tartrate Usage And Synthesis |
| Chemical Properties | Diethyl tartrate has a mild, fruity, wine aroma. | | Chemical Properties | Colorless to light yellow liqui | | Occurrence | The d-isomer has not been reported found in nature; the l-isomer and the racemic form are of little importance.
Reported found in sherry, white and red wine. | | Uses | (+)-Diethyl L-tartrate is used as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, for Sharpless-type enantioselective oxidation of sulfides to sulfoxides and as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction. It is also used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke therapy. | | Uses | (+)-Diethyl L-tartrate can be used in the synthesis of biologically active compounds such as (+)-altholactone, (-)-aspicilin, (+)-monomorine I and (+)-(1R,2R,3S,6S)-3,6-di-O-methyl conduritol-E. | | Uses | Diethyl L-(+)-Tartrate is used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke thera
py. | | General Description | Made from natural tartaric acid | | Flammability and Explosibility | Non flammable | | Synthesis | (1) 30 g of L-(+)-tartaric acid was added to a 500 mL three-necked flask followed by 150 mL of anhydrous ethanol. The stirrer was turned on to make the mixture homogeneously mixed, and the reaction temperature was controlled in the range of 0 to 30 °C. 95.4 g of thionyl chloride was slowly added dropwise for 1.5 h, taking care to control the rate of dropwise acceleration to manage the exothermic process. After the dropwise addition, the reaction system was warmed up to 50 °C and the reaction was continued for 2 hours. After completion of the reaction, ethanol was removed by distillation under reduced pressure to obtain the crude product of diethyl L-(+)-tartarate. (2) To the above crude product, 3.3 g of potassium bicarbonate was added, the temperature was raised to 20 °C and the reaction was stirred for 3 hours. At the end of the reaction, the solid insoluble matter was removed by filtration to obtain 39.6 g of L-(+)-diethyl L-tartrate, and the product was a colorless or light yellow oily liquid with a molar yield of 96.2%. The purity of the product was tested to be 99.4%. | | References | [1] Tetrahedron Letters, 2013, vol. 54, # 36, p. 4851 - 4853
[2] RSC Advances, 2015, vol. 5, # 15, p. 11687 - 11696
[3] Patent: CN107337603, 2017, A. Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031-0040
[4] Journal of Organic Chemistry, 2012, vol. 77, # 19, p. 8465 - 8479,15
[5] Patent: CN106966943, 2017, A. Location in patent: Paragraph 0090; 0091 |
| | L(+)-Diethyl L-tartrate Preparation Products And Raw materials |
| Raw materials | D(-)-Tartaric acid-->DL-Tartaric acid-->Diethyl DL-tartrate-->Ethanol-->L(+)-Tartaric acid | | Preparation Products | (+)-DIOP-->(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol-->N,N,N',N'-Tetramethyl-L-tartramide-->1,3-Dioxolane-4,5-dicarboxylic acid, 2-(2-phenylethenyl)-, diethyl ester, [4R-[2α(E),4α,5β]]- (9CI)-->1,4-Butanedione, 2,3-dihydroxy-1,4-di-1-pyrrolidinyl-, (2R,3R)--->3-diMethoxysuccinate |
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