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775924

Sigma-Aldrich

4-Benzoylbenzoic acid N-succinimidyl ester

97%

Synonym(s):

4-Benzoylbenzoic acid, succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):
C18H13NO5
CAS Number:
91990-88-4
Molecular Weight:
323.30
MDL number:
MFCD00058572
UNSPSC Code:
12352200
PubChem Substance ID:
329767795

Assay

97%

form

solid

mol wt

323.3

reaction suitability

reagent type: cross-linking reagent

mp

207-212 °C

storage temp.

−20°C

SMILES string

O=C1CCC(=O)N1OC(=O)c2ccc(cc2)C(=O)c3ccccc3

InChI

1S/C18H13NO5/c20-15-10-11-16(21)19(15)24-18(23)14-8-6-13(7-9-14)17(22)12-4-2-1-3-5-12/h1-9H,10-11H2

InChI key

MVQNJLJLEGZFGP-UHFFFAOYSA-N

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Application

Heterobifunctional photoreactive crosslinker. Succinimidyl ester will react with amines and the benzophenone will react non-specifically upon photoirradiation at approximately 360 nm.
A benzophenone-based photoreactive reagent shown to be useful for synthesizing photoreactive peptides and oligonucleotides.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273

Hazard Classifications

Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBN7485

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Horacio F Olivo et al.
Bioorganic & medicinal chemistry letters, 20(3), 1153-1155 (2009-12-25)
We have synthesized an analog of dehydroepiandrosterone (DHEA, 1) containing both a benzophenone (BP) and a biotin (Bt) group (DHEA-BP-Bt, 8). Compound 8 was prepared by functionalization on C-17 of 1. Biocytin was reacted with 4-benzoylbenzoic acid and the product
Dan Bernardi et al.
Bioorganic & medicinal chemistry letters, 16(6), 1601-1604 (2006-01-03)
The first synthesis of an N-acylated photoactivatable analogue of reduced glutathione is described. N-(4-Benzoylbenzoyl)glutathione (8) was found to be an inhibitor and a photoaffinity probe of purified rat liver glutathione S-transferases.

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