3-(1H-imidazol-4-yl)prop-2-enoic acid

• ChemBase编号: 1738
• 分子式: C6H6N2O2
• 平均质量: 138.12404
• 单一同位素质量: 138.04292744
• SMILES: OC(=O)/C=C/c1c[nH]cn1
• Canonical SMILES: OC(=O)/C=C/c1c[nH]cn1
• 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

名称和登记号

名称

• IUPAC标准名: 3-(1H-imidazol-4-yl)prop-2-enoic acid; (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid; (2E)-3-(1H-imidazol-5-yl)prop-2-enoic acid; 3-(1H-imidazol-5-yl)prop-2-enoic acid
• IUPAC传统名: urocanic acid; (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid; trans-urocanic acid; (2E)-3-(3H-imidazol-4-yl)prop-2-enoic acid
• 别名: 3-(4-咪唑基)丙烯酸; 尿刊酸; 4-咪唑丙烯酸; 4-Imidazoleacrylic acid; 4-Imidazoleacrylic acid; 3-(4-Imidazolyl)acrylic acid; UROCANIC ACID; (E)-3-(1H-imidazol-4-yl)acrylic acid; cis-3-(1H-imidazol-4-yl)-2-propenoic acid; cis-UCA; cis-Urocanic acid; 3-(1H-imidazol-4-yl)acrylic acid; 3-(1 H -Imidazol-4-yl)-2-propenoic acid; 4-Imidazoleacrylic acid; Urocaninic acid; Urocanic acid; (2e)-3-(1h-Imidazol-4-Yl)Acrylic Acid; (E)-3-(1H-Imidazol-5-yl)-2-propenoic acid; Urocanic acid

登记号

• CAS号: 7699-35-6; 104-98-3
• EC号: 203-258-4
• MDL号: MFCD01593677; MFCD00005203; MFCD11045310
• Beilstein号: 81405
• PubChem SID: 160965194; 24888491
• PubChem CID: 1178; 736715
• 医学主题词(MeSH): Urocanic+acid
• 维基百科标题: Urocanic_acid

理论计算性质

JChem

• Acid pKa: 3.8470757
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -1.0751153
• LogD (pH = 7.4): -2.2414906
• Log P: -1.0052562
• 摩尔折射率: 35.5676 cm^3
• 极化性: 13.067313 Å^3
• 极化表面积: 65.98 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.0
• LOG S: -0.82
• 溶解度: 2.10e+01 g/l

分子性质

理化性质

• 溶解度: 1.5 mg/mL at 17 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; H2O: >10 mg/mL
• 外观: white solid (fluffy)
• 熔点: >215°C(dec); 225°C; 226-228 °C(lit.); dec > 215 °C

安全信息

• 保存条件: 2-8°C; Light sensitive; protect from light
• 保存注意事项: IRRITANT
• RTECS编号: NI3425200
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: R:36/37/38
• 安全公开号: S:20-25-26-37/39
• TSCA收录: false
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C; 2-8°C

药理学性质

• 生物活性机理: Gabaminergic

产品相关信息

• 纯度: >95%; ≥98% (HPLC); ≥99.0% (T); 99%
• 级别: purum
• 应用领域: Shows antineoplastic activity; Sunscreen
• Empirical Formula (Hill Notation): C6H6N2O2

详细说明

MP Biomedicals - 02103221

Crystalline

MP Biomedicals - 05206291

MP Biomedicals Rare Chemical collection

DrugBank - DB01971

Drug information: experimental

Sigma Aldrich - U6883

Biochem/physiol Actions
cis-Urocanic acid, a 5-HT agonist, is a product of uv isomerization of trans-urocanic acid in skin, which leads to immunosuppression via activation of 5-HT2A receptor.

Sigma Aldrich - 859796

包装
25, 100 g in poly bottle
5 g in glass bottle

参考文献

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 492A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 621A, (ir)
• Edlbacher, S. et al., Hoppe Seyler's Z. Physiol. Chem., 1942, 276, 126; 1943, 279, 63, (isol, biosynth)
• Biochem. Prep., 1955, 4, 50, (synth)
• Gregoire, J. et al., Bull. Soc. Chim. Belg., 1958, 40, 767, (isol)
• List, F.H. et al., Hoppe Seyler's Z. Physiol. Chem., 1960, 319, 17, (isol)
• Japan. Pat., 1961, 61 23 094; CA, 60, 2302, (isol)
• Baden, H. et al., Nature (London), 1966, 210, 732, (pmr)
• Shibatari, T. et al., Appl. Microbiol., 1974, 27, 688, (biosynth)
• Svinning, T., Acta Cryst. B, 1979, 35, 2813, (cryst struct)
• Ienaga, K. et al., J. Het. Chem., 1988, 25, 1037, (deriv)
• Hanson, K.M. et al., J.A.C.S., 1997, 119, 2715, (spectra)