HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetylmandelate
(R)-2-acetoxy-2-phenylacetic acid · (-)-D-Mandelic acid acetate · 2(R)-acetoxy-2-phenylacetic acid · -D-mandeL · (-)-O-AcetyL · Mandelic acid 12 · (-)-O-Acetylmandelic acid · R - 0 - ACETYLMANDELIC ACID
Identifiers & Physical Properties
| CAS No. | 51019-43-3 |
|---|---|
| Molecular formula | C10H10O4 |
| Average molar mass | 194.18 g/mol |
| Monoisotopic mass | 194.0579088 g/mol |
| SMILES | CC(=O)OC(=O)C(O)c1ccccc1 |
| InChIKey | DQVWXLRNCXQVKH-UHFFFAOYSA-N |
| PubChem CID | 20537972 |
| DTXSID | DTXSID70965293 |
Chemical & Physical Properties
| XLogP | 0.9 |
|---|---|
| Topological polar surface area | 63.6 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 4 |
| Heavy atoms | 14 |
| Formal charge | 0 |
| Complexity | 218 |
| Melting point | 97-99 °C(lit.) |
| Boiling point | 317.8±30.0 °C(Predicted) |
| Density | 1.259±0.06 g/cm3(Predicted) |
| Refractive index | -153 ° (C=2, Acetone) |
| Storage conditions | Inert atmosphere,Store in freezer, under -20°C |
| Solubility | Soluble in methanol. (almost transparency) |
| pKa (acidity coefficient) | 2.76±0.10(Predicted) |
| Physical state | powder to crystal |
| Color | White to Almost white |
| optical activity | [α]20/D 152.4°, c = 2 in acetone |
| BRN | 2694110 |
| Cosmetics Ingredients Functions | BUFFERING |
| InChI | InChI=1/C10H10O4/c1-7(11)14-9(10(12)13)8-5-3-2-4-6-8/h2-6,9H,1H3,(H,12,13)/t9-/s3 |
| InChIKey | YCCSWLJUVZBEAS-SECBINFHSA-N |
| SMILES | [C@@H](C1C=CC=CC=1)(C(=O)O)OC(=O)C |&1:0,r| |
| LogP (partition coefficient) | 1.780 (est) |
| CAS DataBase Reference | 51019-43-3(CAS DataBase Reference) |
| UNSPSC Code | 12352108 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 22-24/25-60-37-26 |
| Water hazard class (WGK) | 3 |
| Customs code | 29181990 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Active |
Safety & Regulations
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
|---|---|
| Water hazard class (WGK) | 3 |
| Customs code | 29181990 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Safety statements (S) | 22-24/25-60-37-26 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| GHS precautionary statements | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
Uses
The (R)- and (S)-isomers are chiral derivatizing agents for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines.
Uses
(R)-(-)-O-Acetylmandelic acid may be used as a precursor to prepare a chiral diamine, which is an intermediate to prepare Utenone A. It may also be used to prepare ethyl (2′R)-2′-acetoxy-2′-phenylethanoate.
General Description
(R)-(-)-O-Acetylmandelic acid is a chiral derivatizing agent for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines.