2,5-dioxopyrrolidin-1-yl 3-(4-hydroxyphenyl)propanoate

• ChemBase ID: 105948
• Molecular Formular: C13H13NO5
• Molecular Mass: 263.24602
• Monoisotopic Mass: 263.07937252
• SMILES: Oc1ccc(CCC(=O)ON2C(=O)CCC2=O)cc1
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCc1ccc(cc1)O
• InChI: InChI=1S/C13H13NO5/c15-10-4-1-9(2-5-10)3-8-13(18)19-14-11(16)6-7-12(14)17/h1-2,4-5,15H,3,6-8H2
• InChIKey: KYRUKRFVOACELK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-(4-hydroxyphenyl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-(4-hydroxyphenyl)propanoate
• Synonyms: SHPP; 3-(4-Hydroxyphenyl)propionic acid N-hydroxysuccinimide ester; Bolton-Hunter Reagent; 3-(p-HYDROXYPHENYL) PROPIONIC ACID N-HYDROXYSUCCINIMIDE ESTER; N-[(4-Hydroxyhydrocinnamoyl)oxy]succinimide; N-Succinimidyl 3-(4-hydroxyphenyl)propionate; Bolton-Hunter reagent precursor; Rudinger reagent; N-[(4-羟基氢化肉桂酰基)氧基]琥珀酰亚胺; N-琥珀酰亚胺 3-(4-羟基苯基)丙酸酯; Bolton-Hunter 试剂前体; Rudinger 试剂; 羟苯基丙酸 N-羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 34071-95-9
• EC Number: 251-818-1
• MDL Number: MFCD00005515
• Beilstein Number: 1545011
• PubChem SID: 24879981; 162092698; 24895444
• PubChem CID: 99557

CALCULATED PROPERTIES

• Acid pKa: 9.505235
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.1215402
• LogD (pH = 7.4): 1.1182075
• Log P: 1.1215829
• Molar Refractivity: 64.5013 cm^3
• Polarizability: 25.237562 Å^3
• Polar Surface Area: 83.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 132-133 °C(lit.); 143-145°C
• Fluorescence: λex 320 nm; λem 409 nm in 0.1 M Tris pH 8.8, 2 mM H2O2, peroxidase

Safety Information

• Storage Condition: 2-8°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ~90%; ≥97.0% (C); 90%; 97%
• Grade: technical grade
• Suitability: suitable for fluorescence
• Impurities: 10% isopropyl ether
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C13H13NO5

DETAILS

MP Biomedicals - 02195227

Can be radioiodinated to I^1 ^2 ^5 containing acetylating agent for labeling proteins and peptides.

Sigma Aldrich - 56189

Other Notes
An intermediate for high 128I-labeling of proteins (applications for radioimmunoassay)1,2

Sigma Aldrich - H1256

Application
试剂发生放射性碘化反应后，可作为蛋白质和肽的含 125I 酰化剂。

REFERENCES

• Bolton, A.E. and Hunter, W.M., Biochem. J. , 133 : 529, (1973).
• Bolander, F.F., Jr., and Fellows, R.E., Biochemistry , 14 : 2938, (1975).