776181

Sigma-Aldrich

3-(2-Acetoxy-4,6-dimethylphenyl)-3-methylbutyric acid N-succinimidyl ester

95%

Synonym(s):
Trimethyl lock NHS, Trimethyl lock succinimidyl ester, 3-(2-Acetoxy-4,6-dimethylphenyl)-3-methylbutyric acid N-hydroxysuccinimide ester
Empirical Formula (Hill Notation):
C19H23NO6
Molecular Weight:
361.39
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

mp

107-112 °C

storage temp.

2-8°C

SMILES string

CC(=O)Oc1cc(C)cc(C)c1C(C)(C)CC(=O)ON2C(=O)CCC2=O

InChI

1S/C19H23NO6/c1-11-8-12(2)18(14(9-11)25-13(3)21)19(4,5)10-17(24)26-20-15(22)6-7-16(20)23/h8-9H,6-7,10H2,1-5H3

InChI key

KMNOKEFBKJGRFL-UHFFFAOYSA-N

Application

This ′trimethyl lock′ derivative is activated with a succinimidyl ester for modification of amine containing compounds and biomolecules. After modification of your amine of interest, your now ′masked′ molecule can be released by cleavage of the ester, which can be achieved by cellular esterases. This triggers a rapid lactonization reaction of the ′trimethyl lock′ to regenerate your original amine-containing molecule. This approach has been applied to release of fluorophores, peptides, nucleic acids as well as small molecule drugs.

Packaging

50 mg in clear glass bottle
250 mg in amber glass bottle

pictograms

Exclamation mark

signalword

Warning

hcodes

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

Michael N Levine et al.
Chemical science, 3(8), 2412-2420 (2012-11-28)
The trimethyl lock is an o-hydroxydihydrocinnamic acid derivative in which unfavorable steric interactions between three pendant methyl groups encourage lactonization to form a hydrocoumarin. This reaction is extremely rapid, even when the electrophile is an amide and the leaving group...
Michael N Levine et al.
Molecules (Basel, Switzerland), 13(2), 204-211 (2008-02-29)
p-Nitrophenyl acetate is the most commonly used substrate for detecting the catalytic activity of esterases, including those that activate prodrugs in human cells. This substrate is unstable in aqueous solution, limiting its utility. Here, a stable chromogenic substrate for esterases...

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