Home Imidazoles 3465-72-3
3465-72-3,MFCD00149316
Catalog No.:AA00329C

3465-72-3 | (E)-3-(1H-Imidazol-5-yl)acrylic acid

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1g
98%
in stock  
$46.00   $32.00
- +
5g
98%
in stock  
$138.00   $96.00
- +
25g
98%
in stock  
$676.00   $473.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00329C
Chemical Name:
(E)-3-(1H-Imidazol-5-yl)acrylic acid
CAS Number:
3465-72-3
Molecular Formula:
C6H6N2O2
Molecular Weight:
138.1240
MDL Number:
MFCD00149316
SMILES:
OC(=O)/C=C/c1c[nH]cn1
Properties
Properties
 
BP:
456.9°C at 760 mmHg  
Form:
Solid  
MP:
225℃  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
156  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  

Literature

Title: Filaggrin deficiency leads to impaired lipid profile and altered acidification pathways in a 3D skin construct.

Journal: The Journal of investigative dermatology 20140301

Title: Urocanate reductase: identification of a novel anaerobic respiratory pathway in Shewanella oneidensis MR-1.

Journal: Molecular microbiology 20121201

Title: Development and validation of an ion-pair chromatographic method for simultaneous determination of trans- and cis-urocanic acid in fish samples.

Journal: Journal of chromatography. A 20120921

Title: Topical cis-urocanic acid attenuates oedema and erythema in acute and subacute skin inflammation in the mouse.

Journal: The British journal of dermatology 20120901

Title: Microwave spectrum, structure, tautomeric, and conformational composition of 4-vinylimidazole.

Journal: The Journal of chemical physics 20120814

Title: Variation in transport explains polymorphism of histidine and urocanate utilization in a natural Pseudomonas population.

Journal: Environmental microbiology 20120801

Title: 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: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120515

Title: Antitumor effects of cis-urocanic acid on experimental urothelial cell carcinoma of the bladder.

Journal: The Journal of urology 20120401

Title: Metabolomics applied to urine samples in childhood asthma; differentiation between asthma phenotypes and identification of relevant metabolites.

Journal: Biomedical chromatography : BMC 20120101

Title: Intragenic copy number variation within filaggrin contributes to the risk of atopic dermatitis with a dose-dependent effect.

Journal: The Journal of investigative dermatology 20120101

Title: Expression of VjbR under nutrient limitation conditions is regulated at the post-transcriptional level by specific acidic pH values and urocanic acid.

Journal: PloS one 20120101

Title: Caspase-14 is required for filaggrin degradation to natural moisturizing factors in the skin.

Journal: The Journal of investigative dermatology 20111101

Title: Cuts by caspase-14 control the proteolysis of filaggrin.

Journal: The Journal of investigative dermatology 20111101

Title: Levels of filaggrin degradation products are influenced by both filaggrin genotype and atopic dermatitis severity.

Journal: Allergy 20110701

Title: 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.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20110701

Title: Characterizing the composition of underarm and forearm skin using confocal raman spectroscopy.

Journal: International journal of cosmetic science 20110601

Title: cis-Urocanic acid enhances prostaglandin E2 release and apoptotic cell death via reactive oxygen species in human keratinocytes.

Journal: The Journal of investigative dermatology 20110601

Title: Systemic low-dose UVB inhibits CD8 T cells and skin inflammation by alternative and novel mechanisms.

Journal: The American journal of pathology 20110601

Title: Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.

Journal: European journal of medicinal chemistry 20110501

Title: The role of tautomers in the UV absorption of urocanic acid.

Journal: Physical chemistry chemical physics : PCCP 20110314

Title: Towards non-peptide ANG II AT1 receptor antagonists based on urocanic acid: rational design, synthesis and biological evaluation.

Journal: Amino acids 20110201

Title: Urocanic acid as an efficient hydroxyl radical scavenger: a quantum theoretical study.

Journal: Journal of molecular modeling 20110101

Title: Increased sensitivity of histidinemic mice to UVB radiation suggests a crucial role of endogenous urocanic acid in photoprotection.

Journal: The Journal of investigative dermatology 20110101

Title: Urocanic acid in the skin: a mixed blessing?

Journal: The Journal of investigative dermatology 20110101

Title: [Moderation is best also in sunbathing].

Journal: Duodecim; laaketieteellinen aikakauskirja 20110101

Title: Cis-urocanic acid inhibits SAPK/JNK signaling pathway in UV-B exposed human corneal epithelial cells in vitro.

Journal: Molecular vision 20110101

Title: Effect of filaggrin breakdown products on growth of and protein expression by Staphylococcus aureus.

Journal: The Journal of allergy and clinical immunology 20101201

Title: Urocanic acid suppresses induction of immunity in human skin.

Journal: Photodermatology, photoimmunology & photomedicine 20101201

Title: Protodynamic intracellular acidification by cis-urocanic acid promotes apoptosis of melanoma cells in vitro and in vivo.

Journal: The Journal of investigative dermatology 20101001

Title: Knockdown of filaggrin impairs diffusion barrier function and increases UV sensitivity in a human skin model.

Journal: The Journal of investigative dermatology 20100901

Title: Is the filaggrin-histidine-urocanic acid pathway essential for stratum corneum acidification?

Journal: The Journal of investigative dermatology 20100801

Title: Agents that reverse UV-Induced immune suppression and photocarcinogenesis affect DNA repair.

Journal: The Journal of investigative dermatology 20100501

Title: The evaluation of the amount of cis- and trans-urocanic acid in the stratum corneum by Raman spectroscopy.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20100501

Title: Catalytic molecularly imprinted polymer membranes: development of the biomimetic sensor for phenols detection.

Journal: Analytica chimica acta 20100205

Title: Inhibition of histidine ammonia lyase by 8-methoxypsoralen and psoralen-oxidized photoproducts.

Journal: Photochemistry and photobiology 20100101

Title: Molecular targets for the protodynamic action of cis-urocanic acid in human bladder carcinoma cells.

Journal: BMC cancer 20100101

Title: cis-Urocanic acid attenuates acute dextran sodium sulphate-induced intestinal inflammation.

Journal: PloS one 20100101

Title: Protodynamic therapy for bladder cancer: in vitro results of a novel treatment concept.

Journal: BJU international 20091101

Title: cis-Urocanic acid stimulates primary human keratinocytes independently of serotonin or platelet-activating factor receptors.

Journal: The Journal of investigative dermatology 20091101

Title: Interdependence between heme oxygenase-1 induction and estrogen-receptor-beta signaling mediates photoimmune protection by UVA radiation in mice.

Journal: The Journal of investigative dermatology 20091101

Title: Natural moisturizing factor components in the stratum corneum as biomarkers of filaggrin genotype: evaluation of minimally invasive methods.

Journal: The British journal of dermatology 20091101

Title: Molecular basis for cis-urocanic acid as a 5-HT(2A) receptor agonist.

Journal: Bioorganic & medicinal chemistry letters 20090915

Title: Mutations in the urocanase gene UROC1 are associated with urocanic aciduria.

Journal: Journal of medical genetics 20090601

Title: Eczema genetics: current state of knowledge and future goals.

Journal: The Journal of investigative dermatology 20090301

Title: Effects of intramammary infusion of cis-urocanic acid on mastitis-associated inflammation and tissue injury in dairy cows.

Journal: American journal of veterinary research 20090301

Title: Cis-urocanic acid suppresses UV-B-induced interleukin-6 and -8 secretion and cytotoxicity in human corneal and conjunctival epithelial cells in vitro.

Journal: Molecular vision 20090101

Title: [Synthesis and characterization of urocanic acid-coupled chitosan as gene vector].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20081201

Title: In vivo evaluation of the protective capacity of sunscreen by monitoring urocanic acid isomer in the stratum corneum using Raman spectroscopy.

Journal: 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

Title: Sweat electrolyte concentrations obtained from within occlusive coverings are falsely high because sweat itself leaches skin electrolytes.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 20081001

Title: Screening of urocanic acid isomers in human basal and squamous cell carcinoma tumors compared with tumor periphery and healthy skin.

Journal: Experimental dermatology 20081001

Title: A role for ultraviolet radiation immunosuppression in non-melanoma skin cancer as evidenced by gene-environment interactions.

Journal: Carcinogenesis 20081001

Title: cis-Urocanic acid initiates gene transcription in primary human keratinocytes.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20080701

Title: Recent advances in urocanic acid photochemistry, photobiology and photoimmunology.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080601

Title: Theoretical investigation of the photosensitization mechanisms of urocanic acid.

Journal: Journal of photochemistry and photobiology. B, Biology 20080529

Title: Urocanic acid-modified chitosan-mediated PTEN delivery via aerosol suppressed lung tumorigenesis in K-ras(LA1) mice.

Journal: Cancer gene therapy 20080501

Title: The direct precursor of the pyrimidine moiety of thiamin is not urocanic acid but histidine in Saccharomyces cerevisiae.

Journal: Journal of nutritional science and vitaminology 20080201

Title: Distribution of urocanic acid isomers between aqueous solutions and n-octanol, liposomes or bovine serum albumin.

Journal: Journal of photochemistry and photobiology. B, Biology 20080130

Title: Molecular and cellular mechanisms of photocarcinogenesis.

Journal: Photochemistry and photobiology 20080101

Title: Automated autofluorescence background subtraction algorithm for biomedical Raman spectroscopy.

Journal: Applied spectroscopy 20071101

Title: Sunlight and skin cancer: lessons from the immune system.

Journal: Molecular carcinogenesis 20070801

Title: Looking ahead by looking back.

Journal: The Journal of investigative dermatology 20070101

Title: Effect of cis-urocanic acid on bovine neutrophil generation of reactive oxygen species.

Journal: Journal of dairy science 20061101

Title: The receptor for cis-urocanic acid remains elusive.

Journal: The Journal of investigative dermatology 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: 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.

Journal: Molecular cancer therapeutics 20060401

Title: Polypodium leucotomos extract inhibits trans-urocanic acid photoisomerization and photodecomposition.

Journal: Journal of photochemistry and photobiology. B, Biology 20060301

Title: The effect of clinical UVA/B exposures on urinary urocanic acid isomer levels in individuals with caucasian type (II/III) skin types.

Journal: Dermatology online journal 20051201

Title: An action spectrum for the production of cis-urocanic acid in human skin in vivo.

Journal: The Journal of investigative dermatology 20050501

Title: Molecular characterization of histidinemia: identification of four missense mutations in the histidase gene.

Journal: Human genetics 20050401

Title: Ultraviolet A (320-400 nm) modulation of ultraviolet B (290-320 nm)-induced immune suppression is mediated by carbon monoxide.

Journal: The Journal of investigative dermatology 20050301

Title: Combined dermal exposure to permethrin and cis-urocanic acid suppresses the contact hypersensitivity response in C57BL/6N mice in an additive manner.

Journal: Journal of photochemistry and photobiology. B, Biology 20050114

Title: Enhancement of riboflavin-mediated photo-oxidation of glucose 6-phosphate dehydrogenase by urocanic acid.

Journal: Photochemistry and photobiology 20050101

Title: Interaction and reactivity of urocanic acid towards peroxyl radicals.

Journal: Redox report : communications in free radical research 20050101

Title: Ring-substituted imidazoles as a new class of anti-tuberculosis agents.

Journal: European journal of medicinal chemistry 20040901

Title: Association of nonmelanoma skin cancer with second malignancy.

Journal: Cancer 20040701

Title: 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.

Journal: Photodermatology, photoimmunology & photomedicine 20040201

Title: Protection from inflammation, immunosuppression and carcinogenesis induced by UV radiation in mice by topical Pycnogenol.

Journal: Photochemistry and photobiology 20040201

Title: Suppression of different phases of systemic contact hypersensitivity by urocanic acid oxidation products.

Journal: Photochemistry and photobiology 20040101

Title: The effect of molecular environment on the photoisomerization of urocanic acid.

Journal: Photochemistry and photobiology 20040101

Title: Efficient gene delivery by urocanic acid-modified chitosan.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20031212

Title: Molecular mechanisms of cis-urocanic acid and permethrin-induced alterations in cutaneous immunity.

Journal: Photodermatology, photoimmunology & photomedicine 20031201

Title: Reactive oxygen species formation by UV-A irradiation of urocanic acid and the role of trace metals in this chemistry.

Journal: Photochemistry and photobiology 20031201

Title: Biosynthesis of vitamin B1 in yeast. Derivation of the pyrimidine unit from pyridoxine and histidine. Intermediacy of urocanic acid.

Journal: Journal of the American Chemical Society 20031029

Title: 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.

Journal: Electrophoresis 20030901

Title: Viability of the antigen determines whether DNA or urocanic acid act as initiator molecules for UV-induced suppression of delayed-type hypersensitivity.

Journal: Photochemistry and photobiology 20030901

Title: [Urocanic acid and its role in the photoimmunomodulation process].

Journal: Casopis lekaru ceskych 20030801

Title: Immunotoxic effects of cis-urocanic acid exposure in C57BL/6N and C3H/HeN mice.

Journal: Photochemistry and photobiology 20030401

Title: Epidermal cis-urocanic acid levels correlate with lower specific cellular immune responses after hepatitis B vaccination of ultraviolet B-exposed humans.

Journal: Photochemistry and photobiology 20030301

Title: Cis-urocanic acid increases immunotoxicity and lethality of dermally administered permethrin in C57BL/6N mice.

Journal: International journal of toxicology 20030101

Title: The effects of UV waveband and cis-urocanic acid on tumour outgrowth in mice.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20021201

Title: Interference-based electrochemical biosensor for the measurement of the concentration and isomer ratio of urocanic acid.

Journal: Analytical chemistry 20021001

Title: UV-induced skin changes due to regular use of commercial sunbeds.

Journal: Photodermatology, photoimmunology & photomedicine 20021001

Title: Studies to determine the immunomodulating effects of cis-urocanic acid.

Journal: Methods (San Diego, Calif.) 20020901

Title: Mast cells, neuropeptides, histamine, and prostaglandins in UV-induced systemic immunosuppression.

Journal: Methods (San Diego, Calif.) 20020901

Title: Role of immunomodulation in diseases responsive to phototherapy.

Journal: Methods (San Diego, Calif.) 20020901

Title: Formation of singlet oxygen by urocanic acid by UVA irradiation and some consequences thereof.

Journal: Photochemistry and photobiology 20020601

Title: Correlation analysis of production and photoisomerization of epidermal urocanic acid versus induction and repair of DNA photoproducts in the human skin in situ.

Journal: The Journal of investigative dermatology 20020501

Title: Some photophysical studies of cis- and trans-urocanic acid.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20020501

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Photogeneration and quenching of reactive oxygen species by urocanic acid.

Journal: Journal of the American Chemical Society 20020403

Title: Diffusion of E and Z urocanic amphiphiles through skin and their insertion in a membrane model.

Journal: Skin pharmacology and applied skin physiology 20020101

Title: IL-12 prevents the inhibitory effects of cis-urocanic acid on tumor antigen presentation by Langerhans cells: implications for photocarcinogenesis.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20011201

Title: Interaction of UVB-absorbing sunscreen ingredients with cutaneous molecules may alter photoimmune protection.

Journal: Photochemistry and photobiology 20011201

Title: A TD-DFT study of the photochemistry of urocanic acid in biologically relevant ionic, rotameric, and protomeric forms.

Journal: Journal of the American Chemical Society 20011010

Title: cis-Urocanic acid stimulates neuropeptide release from peripheral sensory nerves.

Journal: The Journal of investigative dermatology 20011001

Title: Mechanisms of photodamage of the skin and its functional consequences for skin ageing.

Journal: Clinical and experimental dermatology 20011001

Title: Disruption of histidine catabolism in NEUT2 mice.

Journal: Archives of biochemistry and biophysics 20010815

Title: Oxidative breakdown and conversion of urocanic acid isomers by hydroxyl radical generating systems.

Journal: Biochimica et biophysica acta 20010615

Title: Effect of dietary histidine content on the change in content of skin urocanic acid isomers in hairless mice irradiated with ultraviolet B.

Journal: Bioscience, biotechnology, and biochemistry 20010601

Title: Simultaneous determination of urocanic acid isomers and histidine in human stratum corneum by high-performance liquid chromatography.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20010601

Title: 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.

Journal: The British journal of dermatology 20010501

Title: Urocanic acid isomers do not modulate intracellular calcium and cyclic AMP in human natural killer cells.

Journal: Acta dermato-venereologica 20010501

Title: Urocanic acid isomers in patients with non-melanoma skin cancer.

Journal: The British journal of dermatology 20010401

Title: UVA exposure affects UVB and cis-urocanic acid-induced systemic suppression of immune responses in Listeria monocytogenes-infected Balb/c mice.

Journal: Photochemistry and photobiology 20010401

Title: The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid.

Journal: Cancer chemotherapy and pharmacology 20010401

Title: Speculation on a role for photoimmunosuppression during space missions.

Journal: Journal of photochemistry and photobiology. B, Biology 20010401

Title: cis-Urocanic acid does not induce the expression of immunosuppressive cytokines in murine keratinocytes.

Journal: Photochemistry and photobiology 20010301

Title: Electronic spectroscopy and photoisomerization of trans-urocanic acid in a supersonic jet.

Journal: Journal of the American Chemical Society 20010207

Title: Malnutrition, urocanic acid, and sun may interact to suppress immunity in sojourners to high altitude.

Journal: Aviation, space, and environmental medicine 20010201

Title: Analysis of histidine and urocanic acid isomers by reversed-phase high-performance liquid chromatography.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010105

Title: Topically applied eicosapentaenoic acid protects against local immunosuppression induced by UVB irradiation, cis-urocanic acid and thymidine dinucleotides.

Journal: Photochemistry and photobiology 20010101

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:3465-72-3 Molecular Formula|3465-72-3 MDL|3465-72-3 SMILES|3465-72-3 (E)-3-(1H-Imidazol-5-yl)acrylic acid