Urocanic Acid
Basic information
- CAS
104-98-3- Standard SMILES
O=C(O)/C=C/c1cnc[nH]1- InChIKey
LOIYMIARKYCTBW-OWOJBTEDSA-N- Molecular formula
- C6H6N2O2
- Average molar mass
- 138.12 g/mol
- Monoisotopic mass
- 138.04292744
Overview
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.
Names & identifiers
- Preferred name
- Urocanic Acid
- IUPAC
- (E)-3-(1H-imidazol-5-yl)prop-2-enoic acid
- English name
- (2E)-3-(1H-Imidazole-4-yl)propenoic acid
- Molecular formula
- C6H6N2O2
- Molecular weight
- 138.12
Names & synonyms
urocanic acid104-98-3Urocaninic acid(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid3-(1H-Imidazol-4-yl)-2-propenoic acidAcid, UrocanicGlyoxalinylacrylic Acid2-Propenoic acid, 3-(1H-imidazol-4-yl)-Acid, GlyoxalinylacrylicG8D26XJJ3B2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (E)-NSC-66357
Show more names
Chebi:30817Trans-uric acid(E)-Urocanic acidtrans-UrocanicAcid>Thiamazole Impurity 5(E)-3-(4-Imidazolyl)acrylic acid(αE)-1H-Imidazole-4-acrylic acid(E)-3-(5-Imidazolyl)acrylic Acid
CHEBI:27248DTXSID50859181RefChem:901492DTXCID10809662203-258-43-(1H-imidazol-5-yl)prop-2-enoic acidtrans-Urocanic acid4-imidazoleacrylic acid
Database identifiers
- CAS
104-98-3、3465-72-3、6198-55-6、7699-35-6- PubChem CID
- 736715
- DTXSID
DTXSID5041148- ChEMBL
CHEMBL1236602- ChEBI
CHEBI:27248- UNII
- G8D26XJJ3B
- EC Number
- 203-258-4
- Nikkaji
- J168.822G、J2.069.797K、J5.039C
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 66 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 156
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsCosmetic ingredients (Urocanic Acid) -> CIR (Cosmetic Ingredient Review)
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Solubility1.5 mg/mL at 17 °C
Melting Point225 °C
Physical DescriptionSolid
Collision Cross Section
134.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
137.54 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
134.1 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
134.8 Ų [M+H]+
Physicochemical properties
- Melting point
- 225 °C · 225 °C
- Boiling point
- 456.9 · 456.9±20.0 °C(Predicted)
- Density
- 1.43 · 1.430±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 3 mg/ml; · DMF: 3 mg/ml; DMSO: 15 mg/ml; PBS (pH 7.2): 0.3 mg/ml
- form
- powder to crystal
- pka
- 3.55 · 3.55±0.10(Predicted)
- color
- White to Almost white
- FDA UNII
- 8 D26XJJ3B · G8D26XJJ3B
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
- HS Code
- 2933.29 · 2933.29.9000
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, 3-(1H-imidazol-5-yl)-
2-Propenoic acid, 3-(1H-imidazol-4-yl)-: Does not have an individual approval but may be used under an appropriate group standard
Imidazole-4-acrylic acid: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Toxicity Summary
The safety of this ingredient has not been documented and substantiated. The CIR Expert Panel cannot conclude whether Urocanic Acid is safe for use in cosmetic products until such time as the appropriate safety data have been obtained and evaluated.
Ingredients for which the data are insufficient and their use in cosmetics is not supported
Safety data
- hs_code
- 2933.29.9000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Tissue LocationsEpidermis
Cellular LocationsCytoplasm
Metabolite PathwaysHistidine metabolism
Uses & manufacturing
UsesCIR ingredient: Urocanic Acid
General Manufacturing Information2-Propenoic acid, 3-(1H-imidazol-5-yl)-: ACTIVE
Applications
Usestrans-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].
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: The trans-isomer of urocanic acid.
Suppliers
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Related reactions
18 records
Compound notes
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