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776181

Sigma-Aldrich

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

95%

Synonym(s):

3-(2-Acetoxy-4,6-dimethylphenyl)-3-methylbutyric acid N-hydroxysuccinimide ester, Trimethyl lock NHS, Trimethyl lock succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):
C19H23NO6
Molecular Weight:
361.39
MDL number:
MFCD24386387
UNSPSC Code:
12352106
PubChem Substance ID:
329767818
NACRES:
NA.22

Assay

95%

form

solid

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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