(2R)-2-hydroxy-2-phenylacetic acid

• ChemBase ID: 70014
• Molecular Formular: C8H8O3
• Molecular Mass: 152.14732
• Monoisotopic Mass: 152.04734412
• SMILES: C(=O)([C@H](O)c1ccccc1)O
• Canonical SMILES: O[C@H](c1ccccc1)C(=O)O
• InChI: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1
• InChIKey: IWYDHOAUDWTVEP-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-hydroxy-2-phenylacetic acid
• IUPAC Traditional name: DL-mandelate; (-)-mandelic acid; (R)-hydroxy(phenyl)acetic acid; mandelic acid, (+-)-
• Synonyms: (R)-α-Hydroxyphenylacetic acid; (R)-(-)-Mandelic acid; α-Hydroxyphenylacetic acid; D-(-)-MANDELIC ACID; (αR)-α-Hydroxybenzeneacetic Acid; D-Mandelic Acid; (-)-(R)-Mandelic Acid; (-)-D-Mandelic Acid; (-)-Mandelic Acid; (-)-α-Hydroxyphenylacetic Acid; (2R)-2-Hydroxy-2-(phenyl)ethanoic Acid; D-2-Phenylglycolic Acid; R-(-) Mandelic acid; (2R)-2-hydroxy-2-phenylacetic acid; D-(-)-Mandelic acid; D-MANDELIC ACID; (R)-(-)-Mandelic acid; (2S)-(+)-alpha-Hydroxyphenylacetic acid; L-(+)-Mandelic acid 98%; (R)-(-)-alpha-Hydroxyphenylacetic acid; (R)-(-)-扁桃酸; (R)-α-羟基苯乙酸; D-(-)-扁桃酸

Database IDs

• CAS Number: 611-71-2; 17199-29-0
• EC Number: 210-276-6
• MDL Number: MFCD00004495; MFCD00064251
• Beilstein Number: 2691094
• PubChem SID: 24849414; 162035739; 24896710
• PubChem CID: 11914

CALCULATED PROPERTIES

• Acid pKa: 3.7512336
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.85347056
• LogD (pH = 7.4): -2.3882656
• Log P: 0.89583564
• Molar Refractivity: 38.7038 cm^3
• Polarizability: 15.161119 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: ~133 °C(lit.); 130-132°C; 130-133 °C; 130-134°C; 131 - 133°C; 131-133 °C(lit.); 131-134°C; 131-135°C
• Flash Point: >190 °C; >374 °F
• Optical Rotation: [α]20/D ~-155°, c = 2.3 in H2O(lit.); [α]20/D -153±5°, c = 5% in H2O; [α]20/D -155±5°, c = 5% in H2O; [α]23/D -153°, c = 2.5 in H2O; [α]25/D -151°, c = 1 in ethanol; -153 (c=5 in water)
• Hydrophobicity(logP): 0.502

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Protect from light
• Storage Warning: IRRITANT; Irritant/Light Sensitive; Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 41
• Safety Statements: 26-39
• TSCA Listed: false; 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338; P280-P305+P351+P338-P310
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); ≥99%; ≥99.0% (T); 95%; 95+%; 98%; 99%; ChiPros 99+%, ee 99+%
• Grade: puriss.; purum; ReagentPlus®
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ≥99:1 (GC)
• Linear Formula: C6H5CH(OH)CO2H
• Empirical Formula (Hill Notation): C8H8O3

DETAILS

MP Biomedicals - 05215998

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102245

Protect from light
Crystalline
Purity: 99%

Sigma Aldrich - M2500

Linkage
扁桃酸异构体的命名比较混乱。该异构体先前的命名为 L(—)扁桃酸。

Sigma Aldrich - 154210

Packaging
25 g in poly bottle
5 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - M2209

Packaging
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 63450

Other Notes
Reagent used for the resolution of bases1,2,3; Resolution of alcohols via esters4; Stereoselective α-alkylation via dioxolanones5

Toronto Research Chemicals - M162530

Antiseptic (urinary).

REFERENCES

• Pessela, B., et al.: Enzyme Microb. Technol., 40, 310 (2007)
• Carrasco-Lopez, C., et al.: J. Biol. Chem., 284, 4365 (2007)
• Reagent for determination of enantiomeric excess of alcohols by chiral HPLC. For determination of ee of amines by NMR, see: J. Org. Chem., 53, 5335 (1988).
• Chiral intermediate and resolving agent for organic bases. For resolution of alcohols as their mandelate esters, see: J. Org. Chem., 48, 3548 (1983). For review of resolution of alcohols, see: Org. React., 2, 376 (1944).