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Trans-Urocanic acid

CAT: 0804-HY-113008B-01Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-113008B-01Size:10 mM - 1 mL
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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].
CAS Number
3465-72-3
Product Name Alternative
(E) -Urocanic acid; trans-UCA
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Endogenous Metabolite
Type
Reference compound
Related Pathways
Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/trans-urocanic-acid.html
Concentration
10mM
Purity
99.94
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(/C=C/C1=CN=CN1)O
Molecular Formula
C6H6N2O2
Molecular Weight
138.12
Precautions
H302, H315, H319, H335
References & Citations
[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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite

Chemical Information

Urocanic Acid

Urocanic acid is an alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine. It has a role as a chromophore and a human metabolite. It is a member of imidazoles and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a urocanate.

CAS Number3465-72-3
PubChem CID736715
IUPAC Name(E)-3-(1H-imidazol-5-yl)prop-2-enoic acid
Molecular FormulaC6H6N2O2
Molecular Weight138.12
XLogP0
Topological Polar Surface Area66
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Heavy Atom Count10
Formal Charge0
Complexity156
SMILES
C1=C(NC=N1)/C=C/C(=O)O
InChI
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
InChIKey
LOIYMIARKYCTBW-OWOJBTEDSA-N
Chemical Structure
2D Structure
2D structure of Urocanic Acid
CAS: 3465-72-3
CID: 736715
Formula: C6H6N2O2
MW: 138.12
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight138.12
XLogP30
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass138.042927438
Monoisotopic Mass138.042927438
Topological Polar Surface Area66 Ų
Heavy Atom Count10
Formal Charge0
Complexity156
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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