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| | (S)-(+)-O-Acetyl-L-mandelic acid Basic information |
| | (S)-(+)-O-Acetyl-L-mandelic acid Chemical Properties |
| Melting point | 98-101 °C | | alpha | 153 º (c=2 in acetone) | | Boiling point | 317.8±30.0 °C(Predicted) | | density | 1.259±0.06 g/cm3(Predicted) | | refractive index | 153 ° (C=2, Acetone) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Acetone, Chloroform | | form | Solid | | pka | 2.76±0.10(Predicted) | | color | White | | Optical Rotation | [α]28/D +153°, c = 2 in acetone | | BRN | 2694109 | | Cosmetics Ingredients Functions | BUFFERING | | InChI | 1S/C10H10O4/c1-7(11)14-9(10(12)13)8-5-3-2-4-6-8/h2-6,9H,1H3,(H,12,13)/t9-/m0/s1 | | InChIKey | YCCSWLJUVZBEAS-VIFPVBQESA-N | | SMILES | CC(=O)O[C@H](C(O)=O)c1ccccc1 | | LogP | 1.780 (est) | | CAS DataBase Reference | 7322-88-5(CAS DataBase Reference) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | HS Code | 29181990 | | Storage Class | 11 - Combustible Solids |
| | (S)-(+)-O-Acetyl-L-mandelic acid Usage And Synthesis |
| Chemical Properties | (S)-(+)-O-Acetyl-L-mandelic acid is white to light yellow crystal powde | | Uses | (S)-(+)-O-Acetyl-L-mandelic acid is an antibacterial used particularly in the treatment of urinary tract infections. | | Uses | The (R)- and (S)-isomers are chiral derivatizing agents for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines. | | Synthesis | Example 1; Preparation of (S)-2-acetoxy-2-phenylacetic acid 1; To a round bottom flask containing mandelic acid (15 g, 111 mmol) was added 100 mL of acetic anhydride. After stirring for 5 min, 10 mL of anhydrous ether and a catalytic amount of DMAP were added sequentially. the reaction mixture was stirred at room temperature for 16 h. The reaction was carried out at room temperature. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure to give an amorphous solid. The solid was dissolved with EtOAc (50 mL) and washed sequentially with 1N HCl (2 x 10 mL), water (2 x 10 mL) and saturated saline (10 mL). The organic phase was dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography with hexane solution of 20% EtOAc as eluent gave the target product (15.8 g, 81 mmol) in 73% yield.The Rf value was 0.54 by TLC (unfolding reagent ratio 1:1 hexane:EtOAc).1H NMR (CDCl3, δ): 11.5 (s, 1H), 7.43 (m, 5H), 5.99 ( s, 1H), 2.20 (s, 3H). | | Purification Methods | Recrystallise it from *benzene/hexane or toluene, and it has characteristic NMR and IR spectra. [Pracejus Justus Liebig | | References | [1] Tetrahedron Asymmetry, 1999, vol. 10, # 19, p. 3701 - 3718
[2] Patent: US2009/215763, 2009, A1. Location in patent: Page/Page column 11
[3] Patent: US2009/311318, 2009, A1. Location in patent: Page/Page column 11-12 |
| | (S)-(+)-O-Acetyl-L-mandelic acid Preparation Products And Raw materials |
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