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Sigma-Aldrich

4-(Aminomethyl)benzoic acid

97%, for peptide synthesis

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Synonym(s):
PAMBA
Linear Formula:
H2NCH2C6H4CO2H
CAS Number:
56-91-7
Molecular Weight:
151.16
Beilstein:
1100606
EC Number:
200-297-9
MDL number:
MFCD00010203
UNSPSC Code:
12352106
eCl@ss:
32160406
PubChem Substance ID:
24857129
NACRES:
NA.22

Quality Level

200

Assay

97%

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

mp

≥300 °C (lit.)

application(s)

peptide synthesis

SMILES string

NCc1ccc(cc1)C(O)=O

InChI

1S/C8H9NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4H,5,9H2,(H,10,11)

InChI key

QCTBMLYLENLHLA-UHFFFAOYSA-N

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Application

4-(Aminomethyl)benzoic acid (PAMBA) can be used in the synthesis of:
  • Cobalt carboxy phosphonates.
  • Apoptozole (Az), which has cellular potency to promote membrane trafficking of mutant cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel activity.
  • Cyclopeptide composed of L-glutamic acid and 3-aminobenzoic acid that can be used as receptors for a variety of cations and anions.
  • A bioactive peptide which has potent GPR54 (a G protein-coupled receptor) agonistic activity.

Other Notes

4-(Aminomethyl)benzoic acid is also an antihemorrhagic agent, which is used for the treatment of internal haemorrhage.

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

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)

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A small molecule that binds to an ATPase domain of Hsc70 promotes membrane trafficking of mutant cystic fibrosis transmembrane conductance regulator.
Cho H J, et al.
Journal of the American Chemical Society, 133(50), 20267-20276 (2011)
M N Iakushenko et al.
Zhurnal mikrobiologii, epidemiologii, i immunobiologii, (1)(1), 77-79 (1998-04-09)
The examination of 49 newborn infants revealed that at the early neonatal period the character of the microbial colonization of the intestine depended on the kind of perinatal pathology: in lesions of the central nervous system and conjugation jaundice the
Carlos F R A C Lima et al.
The journal of physical chemistry. A, 111(42), 10598-10603 (2007-10-05)
The standard (p0 = 0.1 MPa) molar enthalpies of combustion of six aminomethylbenzoic acids were measured at T = 298.15 K by static bomb calorimetry. With these values, the standard molar enthalpies of formation in the crystalline state were obtained.
G A Chalyĭ et al.
Zhurnal mikrobiologii, epidemiologii, i immunobiologii, (1)(1), 62-65 (1993-01-01)
The influence of protease-inhibiting preparations on the development of humoral immune response in diseases involving the development of secondary immunodeficiency (experimentally induced acute pancreatitis and staphylococcal infection) has been studied. Five injections of contrycal and epsilon-aminocaproic acid (epsilon-ACA), starting from
Sandra Osburn et al.
Rapid communications in mass spectrometry : RCM, 21(21), 3409-3419 (2007-09-29)
Formation of [bn+17+cat]+ is a prominent collision-induced dissociation (CID) pathway for Li+- and Na+-cationized peptides. Dissociation of protonated and Ag+-cationized peptides instead favors formation of the rival bn+/[bn-1+cat]+ species. In this study the influence of a 4-aminomethylbenzoic acid (4AMBz) residue
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