trans-Urocanic acid

Names

[ Name ]:
trans-Urocanic acid

[Synonym ]:
2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (2E)-
Trans-Urocanic acid
(E)-3-(1H-Imidazol-5-yl)-2-propenoic acid
(E)-urocanic acid
E-3-(imidazol-4-yl)propenoic acid
(2E)-3-(1H-Imidazol-4-yl)acrylic acid
(Z)-4-pyridalacetophenone
trans-4-imidazoleacrylic acid
(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
(E)-3-(1H-imidazol-4-yl)acrylic acid
1-phenyl-3-(4-pyridinyl)-2-propen-1-one
Urocanic acid
2-propenoic acid, 3-(1H-imidazol-5-yl)-, (2E)-
3-(1H-imidazol-4-yl)prop-2-enoic acid
(E)-3-(1H-imidazol-4-yl)-2-propenoic acid
Urocanate
(E)-3-(imidazol-4-yl)acrylic acid
E-3-(4-Pyridyl)-1-phenylprop-2-en-1-on
4-Imidazoleacrylic Acid
(2E)-3-(1H-Imidazol-5-yl)acrylic acid

Biological Activity

[Description]:

trans-urocanic acid (trans-UCA), a natural epidermal constituent, inhibits human natural killer cell (NK) activity in vitro. trans-urocanic acid is active in regulating an immune function[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

Human Endogenous Metabolite

[In Vitro]

trans-urocanic acid (trans-UCA) partially inhibits cytotoxic function of IL-2-activated NK cells and reduces IL-2-induced activation of NK cells[1]. trans-urocanic acid (trans-UCA;100 μg/mL) slightly decreases cell proliferation and viability of primary human keratinocytes[2]. Cell Proliferation Assay[2] Cell Line: Primary human keratinocytes Concentration: 100 μg/mL Incubation Time: 24 hours Result: Decreased cell proliferation and viability.

[References]

[1]. J Uksila, et al. Trans-urocanic acid, a natural epidermal constituent, inhibits human natural killer cell activity in vitro. Exp Dermatol. 1994 Apr;3(2):61-5.

[2]. Kazuyo Kaneko, et al. cis-Urocanic acid enhances prostaglandin E2 release and apoptotic cell death via reactive oxygen species in human keratinocytes. J Invest Dermatol. 2011 Jun;131(6):1262-71.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
456.9±20.0 °C at 760 mmHg

[ Molecular Formula ]:
C₆H₆N₂O₂

[ Molecular Weight ]:
138.124

[ Flash Point ]:
230.1±21.8 °C

[ Exact Mass ]:
138.042923

[ PSA ]:
65.98000

[ LogP ]:
0.01

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.674

[ Storage condition ]:
2-8C

MSDS

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Safety Information

[ HS Code ]:
2933290090

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%