(2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)pentanedioic acid

• ChemBase ID: 132105
• Molecular Formular: C13H11NO6
• Molecular Mass: 277.22954
• Monoisotopic Mass: 277.05863708
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)[C@@H](CCC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CC[C@H](N1C(=O)c2c(C1=O)cccc2)C(=O)O
• InChI: InChI=1S/C13H11NO6/c15-10(16)6-5-9(13(19)20)14-11(17)7-3-1-2-4-8(7)12(14)18/h1-4,9H,5-6H2,(H,15,16)(H,19,20)/t9-/m0/s1
• InChIKey: FEFFSKLJNYRHQN-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)pentanedioic acid
• IUPAC Traditional name: (2S)-2-(1,3-dioxoisoindol-2-yl)pentanedioic acid
• Synonyms: PhGA; N-Phthaloyl-L-glutamic acid; N-邻苯二甲酰-L-谷氨酸

Database IDs

• CAS Number: 340-90-9
• MDL Number: MFCD00066476
• Beilstein Number: 90136
• PubChem SID: 162226382; 24887505; 24859853
• PubChem CID: 160453

CALCULATED PROPERTIES

• Acid pKa: 2.9141364
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -3.708716
• LogD (pH = 7.4): -6.1939344
• Log P: 0.61069596
• Molar Refractivity: 65.5804 cm^3
• Polarizability: 24.597696 Å^3
• Polar Surface Area: 111.98 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 160-162 °C; 160-162 °C(lit.)
• Optical Rotation: [α]20/D -45°, c = 1 in ethanol; [α]20/D -48±2°, c = 3% in dioxane

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C13H11NO6

DETAILS

Sigma Aldrich - 330418

Packaging
10 g in glass bottle

Sigma Aldrich - 79840

Other Notes
N-protected derivative of L-glutamic acid. The anhydride (prepared with DCCI or Ac2O without racemization) is used for γ-L-glutamylations1,2,3,4; The phthaloyl protection can be removed mildly5