cis-Urocanic acid

Names

[ Name ]:
cis-Urocanic acid

[Synonym ]:
3-[1H-imidazol-4(5)-yl]
Cis-Urocanic Acid-[13C3]
(E)-3-(3H-imidazol-4-yl)prop-2-enoic acid
(Z)-Urocanic acid
cis-Urocanic acid
(Z)-2-propenoic acid
(Z)-3-(1H-imidazol-4-yl)-2-propenoic acid
(2Z)-3-(1H-Imidazole-4-yl)acrylic acid
(Z)-3-(1H-Imidazole-4-yl)acrylic acid
(Z)-3-(1H-imidazol-4-yl)prop-2-enoic acid
UROCANIC ACID, CIS
(Z)-3-(1H-Imidazol-4-yl)propenoic acid

Biological Activity

[Description]:

cis-Urocanic acid is a 5-HT2A receptor agonist. cis-Urocanic acid binds to 5-HT receptor with relatively high affinity (Kd=4.6 nM). cis-Urocanic acid is an immune modulator that induces immunosuppression by binding to the 5-HT2A receptor[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

5-HT2A Receptor

[In Vitro]

Treatment with 100 μg/mL cis-Urocanic acid (cis-UCA) completely suppresses IL-6 and IL-8 secretion, decreases caspase-3 activity, and improves cell viability against UV-B irradiation. No significant effects on IL-6 or IL-8 secretion, caspase-3 activity, or viability of the non-irradiated cells are observed with 100 μg/mL cis-Urocanic acid in both cell types. The 5000 μg/mL concentration is toxic[1]. Cell Viability Assay[1] Cell Line: Human corneal epithelial cells (HCE-2) and human conjunctival epithelial cells (HCECs) Concentration: 10, 100, 1,000, and 5,000 μg/mL Incubation Time: 24, 48, or 72 hours Result: Treatment with 100 μg/mL completely suppressed IL-6 and IL-8 secretion, decreased caspase-3 activity, and improved cell viability against UV-B irradiation. No significant effects on IL-6 or IL-8 secretion, caspase-3 activity, or viability of the non-irradiated cells were observed with 100 μg/mL in both cell types.

[References]

[1]. Walterscheid JP, et al. Cis-urocanic acid, a sunlight-induced immunosuppressive factor, activates immune suppression via the 5-HT2A receptor. Proc Natl Acad Sci U S A. 2006 Nov 14;103(46):17420-5.

[2]. Viiri J, et al. Cis-urocanic acid suppresses UV-B-induced interleukin-6 and -8 secretion and cytotoxicity in human corneal and conjunctival epithelial cells in vitro. Mol Vis. 2009 Sep 8;15:1799-805.

Chemical & Physical Properties

[ Molecular Formula ]:
C₆H₆N₂O₂

[ Molecular Weight ]:
138.12400

[ Exact Mass ]:
138.04300

[ PSA ]:
65.98000

[ LogP ]:
0.50750

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933290090

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%

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