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Sigma-Aldrich

S-Acetylmercaptosuccinic anhydride

96%

Synonym(s):

2-(Acetylthio)succinic anhydride, SAMSA

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About This Item

Empirical Formula (Hill Notation):
C6H6O4S
CAS Number:
6953-60-2
Molecular Weight:
174.17
EC Number:
230-135-2
MDL number:
MFCD00005526
UNSPSC Code:
12162002
PubChem Substance ID:
24851822
NACRES:
NA.23

Quality Level

200

Assay

96%

mp

83-86 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=O)SC1CC(=O)OC1=O

InChI

1S/C6H6O4S/c1-3(7)11-4-2-5(8)10-6(4)9/h4H,2H2,1H3

InChI key

AHTFMWCHTGEJHA-UHFFFAOYSA-N

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General description

S-Acetylmercaptosuccinic anhydride is an amine reactive reagent, containing a sulfhydryl group. The anhydride region opens up, when attacked by an amine nucleophile, forming amine linkage. However, during this ring opening reaction, a free carboxylate group is formed rendering the molecule negatively charged. Activity to proteins and conformation of the molecule us affected by the charge reversal.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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T J Beveridge et al.
Journal of bacteriology, 141(2), 876-887 (1980-02-01)
Amine and carboxyl groups of the cell wall of Bacillus subtilis were chemically modified individually to neutralize their electrochemical charge for determination of their contribution to the metal uptake process. Mild alkali treatment removed ca. 94% of the constituent teichoic
Introduction of sulfhydryl groups into proteins using acetylmercaptosuccinic anhydride
Klotz IM, et al.
Archives of Biochemistry and Biophysics, 96(3), 605-612 (1932)
L Greenfield et al.
Bioconjugate chemistry, 1(6), 400-410 (1990-11-01)
Ricin A chain immunotoxins disulfide cross-linked with conventional, sterically unhindered reagents have unsatisfactorily short circulating life times in vivo. (Acetylthio)succinic anhydride, a thiolating reagent with partial steric hindrance of the sulfur atom, does not remedy this situation. Sulfosuccinimidyl N-[3-(acetylthio)-3-methylbutyryl]-beta- alaninate
Hermanson GT et al.
Bioconjugate Techniques null
Monica A Serban et al.
Biomacromolecules, 8(9), 2821-2828 (2007-08-19)
Hyaluronan (HA) derivatives containing thiol-reactive electrophilic esters were prepared to react with thiol-modified macromolecules to give cross-linker-free hydrogels. Specifically, HA was converted to two haloacetate derivatives, HA bromoacetate (HABA) and HA iodoacetate (HAIA). In cytotoxicity assays, these reactive macromolecules predictably
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