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77951

Sigma-Aldrich

Imidazolepropionic acid

≥98.0% (GC)

Synonym(s):

1H-Imidazole-4-propanoic acid, 1H-Imidazole-5-propanoic acid, 3-(1H-Imidazol-4-yl)propionic acid, 3-(Imidazol-4(5)-yl)propionic acid, Deamino-histidine, Dihydrourocanic acid, NSC 66737

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About This Item

Empirical Formula (Hill Notation):
C6H8N2O2
CAS Number:
1074-59-5
Molecular Weight:
140.14
EC Number:
214-045-0
MDL number:
MFCD18459271
UNSPSC Code:
12352106
PubChem Substance ID:
329768045
NACRES:
NA.25

Assay

≥98.0% (GC)

form

powder

storage temp.

2-8°C

SMILES string

OC(CCC1=CN=CN1)=O

InChI

1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)

InChI key

ZCKYOWGFRHAZIQ-UHFFFAOYSA-N

Biochem/physiol Actions

Imidazolepropionic acid is a product of histidine metabolism, which may involve oxidation or transamination

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

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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A nitrogen-15 nuclear magnetic resonance study of the acid-base and tautomeric equilibriums of 4-substituted imidazoles and its relevance to the catalytic mechanism of .alpha.-lytic protease.
Roberts, J. D. , et al.
Journal of the American Chemical Society, 104, 3945-3949 (1982)
A covalent nicotinamide adenine dinucleotide intermediate in the urocanase reaction.
L H Matherly et al.
Biochemistry, 21(11), 2789-2794 (1982-05-25)
Histidine metabolism in the human adult: histidine blood tolerance, and the effect of continued free L-histidine ingestion on the concentration of imidazole compounds in blood and urine.
W D Block et al.
The Journal of nutrition, 91(2), 189-194 (1967-02-01)
Imidazolepropionic acid as a urinary metabolite of L-histidine.
N P SEN et al.
Biochemical and biophysical research communications, 9, 257-261 (1962-10-17)
Raminta Venskutonytė et al.
Nature communications, 12(1), 1347-1347 (2021-03-03)
The human microbiome can produce metabolites that modulate insulin signaling. Type 2 diabetes patients have increased circulating concentrations of the microbially produced histidine metabolite, imidazole propionate (ImP) and administration of ImP in mice resulted in impaired glucose tolerance. Interestingly, the
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