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3465-72-3

3465-72-3 | (E)-3-(4-Imidazolyl)acrylic acid

CAS No: 3465-72-3 Catalog No: AG0032C4 MDL No:MFCD00005203

Product Description

Catalog Number:
AG0032C4
Chemical Name:
(E)-3-(4-Imidazolyl)acrylic acid
CAS Number:
3465-72-3
Molecular Formula:
C6H6N2O2
Molecular Weight:
138.1240
MDL Number:
MFCD00005203
IUPAC Name:
(E)-3-(1H-imidazol-5-yl)prop-2-enoic acid
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+
InChI Key:
LOIYMIARKYCTBW-OWOJBTEDSA-N
SMILES:
OC(=O)/C=C/c1c[nH]cn1
EC Number:
203-258-4
UNII:
G8D26XJJ3B

Properties

Complexity:
156  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
138.043g/mol
Formal Charge:
0
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
138.126g/mol
Monoisotopic Mass:
138.043g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
66A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0

Literature

Title Journal
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Urocanate reductase: identification of a novel anaerobic respiratory pathway in Shewanella oneidensis MR-1. Molecular microbiology 20121201
Development and validation of an ion-pair chromatographic method for simultaneous determination of trans- and cis-urocanic acid in fish samples. Journal of chromatography. A 20120921
Topical cis-urocanic acid attenuates oedema and erythema in acute and subacute skin inflammation in the mouse. The British journal of dermatology 20120901
Microwave spectrum, structure, tautomeric, and conformational composition of 4-vinylimidazole. The Journal of chemical physics 20120814
Variation in transport explains polymorphism of histidine and urocanate utilization in a natural Pseudomonas population. Environmental microbiology 20120801
Rapid, simultaneous and nanomolar determination of pyroglutamic acid and cis-/trans-urocanic acid in human stratum corneum by hydrophilic interaction liquid chromatography (HILIC)-electrospray ionization tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120515
Antitumor effects of cis-urocanic acid on experimental urothelial cell carcinoma of the bladder. The Journal of urology 20120401
Metabolomics applied to urine samples in childhood asthma; differentiation between asthma phenotypes and identification of relevant metabolites. Biomedical chromatography : BMC 20120101
Intragenic copy number variation within filaggrin contributes to the risk of atopic dermatitis with a dose-dependent effect. The Journal of investigative dermatology 20120101
Expression of VjbR under nutrient limitation conditions is regulated at the post-transcriptional level by specific acidic pH values and urocanic acid. PloS one 20120101
Caspase-14 is required for filaggrin degradation to natural moisturizing factors in the skin. The Journal of investigative dermatology 20111101
Cuts by caspase-14 control the proteolysis of filaggrin. The Journal of investigative dermatology 20111101
Levels of filaggrin degradation products are influenced by both filaggrin genotype and atopic dermatitis severity. Allergy 20110701
Microwave discharge electrodeless lamps (MDEL). Part VII. Photo-isomerization of trans-urocanic acid in aqueous media driven by UV light from a novel Hg-free Dewar-like microwave discharge thermally-insulated electrodeless lamp (MDTIEL). Performance evaluation. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20110701
Characterizing the composition of underarm and forearm skin using confocal raman spectroscopy. International journal of cosmetic science 20110601
cis-Urocanic acid enhances prostaglandin E2 release and apoptotic cell death via reactive oxygen species in human keratinocytes. The Journal of investigative dermatology 20110601
Systemic low-dose UVB inhibits CD8 T cells and skin inflammation by alternative and novel mechanisms. The American journal of pathology 20110601
Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors. European journal of medicinal chemistry 20110501
The role of tautomers in the UV absorption of urocanic acid. Physical chemistry chemical physics : PCCP 20110314
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Increased sensitivity of histidinemic mice to UVB radiation suggests a crucial role of endogenous urocanic acid in photoprotection. The Journal of investigative dermatology 20110101
Urocanic acid in the skin: a mixed blessing? The Journal of investigative dermatology 20110101
[Moderation is best also in sunbathing]. Duodecim; laaketieteellinen aikakauskirja 20110101
Cis-urocanic acid inhibits SAPK/JNK signaling pathway in UV-B exposed human corneal epithelial cells in vitro. Molecular vision 20110101
Effect of filaggrin breakdown products on growth of and protein expression by Staphylococcus aureus. The Journal of allergy and clinical immunology 20101201
Urocanic acid suppresses induction of immunity in human skin. Photodermatology, photoimmunology & photomedicine 20101201
Protodynamic intracellular acidification by cis-urocanic acid promotes apoptosis of melanoma cells in vitro and in vivo. The Journal of investigative dermatology 20101001
Knockdown of filaggrin impairs diffusion barrier function and increases UV sensitivity in a human skin model. The Journal of investigative dermatology 20100901
Is the filaggrin-histidine-urocanic acid pathway essential for stratum corneum acidification? The Journal of investigative dermatology 20100801
Agents that reverse UV-Induced immune suppression and photocarcinogenesis affect DNA repair. The Journal of investigative dermatology 20100501
The evaluation of the amount of cis- and trans-urocanic acid in the stratum corneum by Raman spectroscopy. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20100501
Catalytic molecularly imprinted polymer membranes: development of the biomimetic sensor for phenols detection. Analytica chimica acta 20100205
Inhibition of histidine ammonia lyase by 8-methoxypsoralen and psoralen-oxidized photoproducts. Photochemistry and photobiology 20100101
Molecular targets for the protodynamic action of cis-urocanic acid in human bladder carcinoma cells. BMC cancer 20100101
cis-Urocanic acid attenuates acute dextran sodium sulphate-induced intestinal inflammation. PloS one 20100101
Protodynamic therapy for bladder cancer: in vitro results of a novel treatment concept. BJU international 20091101
cis-Urocanic acid stimulates primary human keratinocytes independently of serotonin or platelet-activating factor receptors. The Journal of investigative dermatology 20091101
Interdependence between heme oxygenase-1 induction and estrogen-receptor-beta signaling mediates photoimmune protection by UVA radiation in mice. The Journal of investigative dermatology 20091101
Natural moisturizing factor components in the stratum corneum as biomarkers of filaggrin genotype: evaluation of minimally invasive methods. The British journal of dermatology 20091101
Molecular basis for cis-urocanic acid as a 5-HT(2A) receptor agonist. Bioorganic & medicinal chemistry letters 20090915
Mutations in the urocanase gene UROC1 are associated with urocanic aciduria. Journal of medical genetics 20090601
Eczema genetics: current state of knowledge and future goals. The Journal of investigative dermatology 20090301
Effects of intramammary infusion of cis-urocanic acid on mastitis-associated inflammation and tissue injury in dairy cows. American journal of veterinary research 20090301
Cis-urocanic acid suppresses UV-B-induced interleukin-6 and -8 secretion and cytotoxicity in human corneal and conjunctival epithelial cells in vitro. Molecular vision 20090101
[Synthesis and characterization of urocanic acid-coupled chitosan as gene vector]. Yao xue xue bao = Acta pharmaceutica Sinica 20081201
In vivo evaluation of the protective capacity of sunscreen by monitoring urocanic acid isomer in the stratum corneum using Raman spectroscopy. Skin research and technology : official journal of International Society for Bioengineering and the Skin (ISBS) [and] International Society for Digital Imaging of Skin (ISDIS) [and] International Society for Skin Imaging (ISSI) 20081101
Sweat electrolyte concentrations obtained from within occlusive coverings are falsely high because sweat itself leaches skin electrolytes. Journal of applied physiology (Bethesda, Md. : 1985) 20081001
Screening of urocanic acid isomers in human basal and squamous cell carcinoma tumors compared with tumor periphery and healthy skin. Experimental dermatology 20081001
A role for ultraviolet radiation immunosuppression in non-melanoma skin cancer as evidenced by gene-environment interactions. Carcinogenesis 20081001
cis-Urocanic acid initiates gene transcription in primary human keratinocytes. Journal of immunology (Baltimore, Md. : 1950) 20080701
Recent advances in urocanic acid photochemistry, photobiology and photoimmunology. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080601
Theoretical investigation of the photosensitization mechanisms of urocanic acid. Journal of photochemistry and photobiology. B, Biology 20080529
Urocanic acid-modified chitosan-mediated PTEN delivery via aerosol suppressed lung tumorigenesis in K-ras(LA1) mice. Cancer gene therapy 20080501
The direct precursor of the pyrimidine moiety of thiamin is not urocanic acid but histidine in Saccharomyces cerevisiae. Journal of nutritional science and vitaminology 20080201
Distribution of urocanic acid isomers between aqueous solutions and n-octanol, liposomes or bovine serum albumin. Journal of photochemistry and photobiology. B, Biology 20080130
Molecular and cellular mechanisms of photocarcinogenesis. Photochemistry and photobiology 20080101
Automated autofluorescence background subtraction algorithm for biomedical Raman spectroscopy. Applied spectroscopy 20071101
Sunlight and skin cancer: lessons from the immune system. Molecular carcinogenesis 20070801
Looking ahead by looking back. The Journal of investigative dermatology 20070101
Effect of cis-urocanic acid on bovine neutrophil generation of reactive oxygen species. Journal of dairy science 20061101
The receptor for cis-urocanic acid remains elusive. The Journal of investigative dermatology 20060501
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Aerosol delivery of urocanic acid-modified chitosan/programmed cell death 4 complex regulated apoptosis, cell cycle, and angiogenesis in lungs of K-ras null mice. Molecular cancer therapeutics 20060401
Polypodium leucotomos extract inhibits trans-urocanic acid photoisomerization and photodecomposition. Journal of photochemistry and photobiology. B, Biology 20060301
The effect of clinical UVA/B exposures on urinary urocanic acid isomer levels in individuals with caucasian type (II/III) skin types. Dermatology online journal 20051201
An action spectrum for the production of cis-urocanic acid in human skin in vivo. The Journal of investigative dermatology 20050501
Molecular characterization of histidinemia: identification of four missense mutations in the histidase gene. Human genetics 20050401
Ultraviolet A (320-400 nm) modulation of ultraviolet B (290-320 nm)-induced immune suppression is mediated by carbon monoxide. The Journal of investigative dermatology 20050301
Combined dermal exposure to permethrin and cis-urocanic acid suppresses the contact hypersensitivity response in C57BL/6N mice in an additive manner. Journal of photochemistry and photobiology. B, Biology 20050114
Enhancement of riboflavin-mediated photo-oxidation of glucose 6-phosphate dehydrogenase by urocanic acid. Photochemistry and photobiology 20050101
Interaction and reactivity of urocanic acid towards peroxyl radicals. Redox report : communications in free radical research 20050101
Ring-substituted imidazoles as a new class of anti-tuberculosis agents. European journal of medicinal chemistry 20040901
Association of nonmelanoma skin cancer with second malignancy. Cancer 20040701
Topical exposure to exogenous ultraviolet-irradiated urocanic acid enhances Mycobacterium ulcerans infection in a Crl:IAF(HA)-hrBR hairless guinea-pig model of Buruli ulcer disease. Photodermatology, photoimmunology & photomedicine 20040201
Protection from inflammation, immunosuppression and carcinogenesis induced by UV radiation in mice by topical Pycnogenol. Photochemistry and photobiology 20040201
Suppression of different phases of systemic contact hypersensitivity by urocanic acid oxidation products. Photochemistry and photobiology 20040101
The effect of molecular environment on the photoisomerization of urocanic acid. Photochemistry and photobiology 20040101
Efficient gene delivery by urocanic acid-modified chitosan. Journal of controlled release : official journal of the Controlled Release Society 20031212
Molecular mechanisms of cis-urocanic acid and permethrin-induced alterations in cutaneous immunity. Photodermatology, photoimmunology & photomedicine 20031201
Reactive oxygen species formation by UV-A irradiation of urocanic acid and the role of trace metals in this chemistry. Photochemistry and photobiology 20031201
Biosynthesis of vitamin B1 in yeast. Derivation of the pyrimidine unit from pyridoxine and histidine. Intermediacy of urocanic acid. Journal of the American Chemical Society 20031029
Formation of S-[2-carboxy-1-(1H-imidazol-4-yl) ethyl]glutathione, a new metabolite of L-histidine, from cis-urocanic acid and glutathione by the action of glutathione S-transferase. Electrophoresis 20030901
Viability of the antigen determines whether DNA or urocanic acid act as initiator molecules for UV-induced suppression of delayed-type hypersensitivity. Photochemistry and photobiology 20030901
[Urocanic acid and its role in the photoimmunomodulation process]. Casopis lekaru ceskych 20030801
Immunotoxic effects of cis-urocanic acid exposure in C57BL/6N and C3H/HeN mice. Photochemistry and photobiology 20030401
Epidermal cis-urocanic acid levels correlate with lower specific cellular immune responses after hepatitis B vaccination of ultraviolet B-exposed humans. Photochemistry and photobiology 20030301
Cis-urocanic acid increases immunotoxicity and lethality of dermally administered permethrin in C57BL/6N mice. International journal of toxicology 20030101
The effects of UV waveband and cis-urocanic acid on tumour outgrowth in mice. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20021201
Interference-based electrochemical biosensor for the measurement of the concentration and isomer ratio of urocanic acid. Analytical chemistry 20021001
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Role of immunomodulation in diseases responsive to phototherapy. Methods (San Diego, Calif.) 20020901
Formation of singlet oxygen by urocanic acid by UVA irradiation and some consequences thereof. Photochemistry and photobiology 20020601
Correlation analysis of production and photoisomerization of epidermal urocanic acid versus induction and repair of DNA photoproducts in the human skin in situ. The Journal of investigative dermatology 20020501
Some photophysical studies of cis- and trans-urocanic acid. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20020501
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
Photogeneration and quenching of reactive oxygen species by urocanic acid. Journal of the American Chemical Society 20020403
Diffusion of E and Z urocanic amphiphiles through skin and their insertion in a membrane model. Skin pharmacology and applied skin physiology 20020101
IL-12 prevents the inhibitory effects of cis-urocanic acid on tumor antigen presentation by Langerhans cells: implications for photocarcinogenesis. Journal of immunology (Baltimore, Md. : 1950) 20011201
Interaction of UVB-absorbing sunscreen ingredients with cutaneous molecules may alter photoimmune protection. Photochemistry and photobiology 20011201
A TD-DFT study of the photochemistry of urocanic acid in biologically relevant ionic, rotameric, and protomeric forms. Journal of the American Chemical Society 20011010
cis-Urocanic acid stimulates neuropeptide release from peripheral sensory nerves. The Journal of investigative dermatology 20011001
Mechanisms of photodamage of the skin and its functional consequences for skin ageing. Clinical and experimental dermatology 20011001
Disruption of histidine catabolism in NEUT2 mice. Archives of biochemistry and biophysics 20010815
Oxidative breakdown and conversion of urocanic acid isomers by hydroxyl radical generating systems. Biochimica et biophysica acta 20010615
Effect of dietary histidine content on the change in content of skin urocanic acid isomers in hairless mice irradiated with ultraviolet B. Bioscience, biotechnology, and biochemistry 20010601
Simultaneous determination of urocanic acid isomers and histidine in human stratum corneum by high-performance liquid chromatography. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20010601
Rethinking the role of tumour necrosis factor-alpha in ultraviolet (UV) B-induced immunosuppression: altered immune response in UV-irradiated TNFR1R2 gene-targeted mutant mice. The British journal of dermatology 20010501
Urocanic acid isomers do not modulate intracellular calcium and cyclic AMP in human natural killer cells. Acta dermato-venereologica 20010501
Urocanic acid isomers in patients with non-melanoma skin cancer. The British journal of dermatology 20010401
UVA exposure affects UVB and cis-urocanic acid-induced systemic suppression of immune responses in Listeria monocytogenes-infected Balb/c mice. Photochemistry and photobiology 20010401
The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid. Cancer chemotherapy and pharmacology 20010401
Speculation on a role for photoimmunosuppression during space missions. Journal of photochemistry and photobiology. B, Biology 20010401
cis-Urocanic acid does not induce the expression of immunosuppressive cytokines in murine keratinocytes. Photochemistry and photobiology 20010301
Electronic spectroscopy and photoisomerization of trans-urocanic acid in a supersonic jet. Journal of the American Chemical Society 20010207
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