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Sigma-Aldrich

4-(Aminomethyl)benzoic acid

97%, for peptide synthesis

Synonym(s):

PAMBA

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About This Item

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

product name

4-(Aminomethyl)benzoic acid, 97%

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

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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Fmoc?based solid?phase synthesis of GPR54?agonistic pentapeptide derivatives containing alkene?and fluoroalkene?dipeptide isosteres.
Tomita K, et al.
Pept. Sci., 88(2), 272-278 (2007)
Shingo Nakajima et al.
Molecular nutrition & food research, 56(5), 753-760 (2012-06-01)
Dietary peptides are potent stimulators of cholecystokinin (CCK) secretion, but the sensing mechanism in CCK-producing cells is poorly understood. Recently, it has been demonstrated that the calcium-sensing receptor (CaSR) mediates CCK secretion induced by amino acids. We investigated the role
Marcus Tirado et al.
Journal of the American Society for Mass Spectrometry, 23(3), 475-482 (2012-01-06)
While recent studies have shown that for some peptides, such as oligoglycines and Leu-enkephalin, mid-sized b fragment ions exist as a mixture of oxazolone and macrocycle structures, other primary structure motifs, such as QWFGLM, are shown to exclusively give rise
Synthesis of model glycolipids having two long alkyl chains.
Z Zhang et al.
Carbohydrate research, 277(2), C1-C3 (1995-11-22)
Large increase in cation binding affinity of artificial cyclopeptide receptors by an allosteric effect.
Kubik S.
Journal of the American Chemical Society, 121(25), 5846-5855 (1999)
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