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Sigma-Aldrich

1-Adamantaneacetic acid

98%

Synonym(s):

1-Adamantylacetic acid

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About This Item

Empirical Formula (Hill Notation):
C12H18O2
CAS Number:
4942-47-6
Molecular Weight:
194.27
Beilstein:
641412
EC Number:
225-585-1
MDL number:
MFCD00074728
UNSPSC Code:
12352100
PubChem Substance ID:
24847774
NACRES:
NA.22

Quality Level

200

Assay

98%

form

chunks

mp

134-137 °C (lit.)

SMILES string

OC(=O)CC12C[C@H]3C[C@H](C[C@H](C3)C1)C2

InChI

1S/C12H18O2/c13-11(14)7-12-4-8-1-9(5-12)3-10(2-8)6-12/h8-10H,1-7H2,(H,13,14)/t8-,9+,10-,12-

InChI key

AOTQGWFNFTVXNQ-GOCCLTDMSA-N

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Application

1-Adamantaneacetic acid was used as an acylating agent in determining pharmacological characteristics of ten new analogues of bradykinin (Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg) that were modified in the N-terminal part of the molecule.

Biochem/physiol Actions

1-Adamantaneacetic acid is an inhibitor of chorismate mutase-prephenate dehydrogenase (EC 1.3.1.12) from Escherichia coli K12 (strain JP 232).

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)

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The Biochemical journal, 165(1), 121-126 (1977-07-01)
Several derivatives of phenylalanine and tyrosine were prepared and tested for inhibition of chorismate mutase-prephenate dehydrogenase (EC 1.3.1.12) from Escherichia coli K12 (strain JP 232). The best inhibitors were N-toluene-p-sulphonyl-L-phenylalanine, N-benzenesulphonyl-L-phenylalanine and N-benzloxycarbonyl-L-phenylalanine. Consequently two compounds, N-toluene-sulphonyl-L-p-aminophenylalanine and N-p-aminobenzenesulphonyl-L-phenylalanine, were
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