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Merck
CN

U6883

Sigma-Aldrich

顺式 -尿烷酸

≥98% (HPLC), solid (fluffy)

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别名:
顺式 -3-(1H-咪唑-4-基)-2-丙烯酸, 顺式 -UCA
经验公式(希尔记法):
C6H6N2O2
CAS号:
分子量:
138.12
MDL编号:
UNSPSC代码:
12352106
PubChem化学物质编号:
NACRES:
NA.77

质量水平

检测方案

≥98% (HPLC)

形式

solid (fluffy)

储存条件

protect from light

颜色

white

溶解性

H2O: >10 mg/mL

储存温度

−20°C

SMILES字符串

OC(=O)\C=C/c1c[nH]cn1

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-UPHRSURJSA-N

应用

cis-尿刊酸(cis-UCA)已被用于:
  • 研究其对自身免疫性脑脊髓炎的保护作用
  • 在线聚焦照明模式下,采用线照明拉曼显微镜技术研究皮肤化学成分的分布
  • 作为标准品,研究cis-UCA水平并检测其对多发性硬化患者免疫反应的影响

生化/生理作用

cis-尿刊酸(cis-UCA)影响身体的免疫细胞,并由于光异构化而随尿液排出。它通过小鼠的光致癌作用抑制肿瘤免疫。cis-尿刊酸已经被研究用来防止紫外线辐射引起的DNA损伤,后者可导致皮肤癌。
-尿烷酸是 5-HT 激动剂,是反式尿烷酸在皮肤中 uv 异构化的产物,通过激活 5-HT 2A 受体导致免疫抑制。

制备说明

顺式尿苷酸可溶于水,浓度大于 10 mg/mL。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


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Jorge Correale et al.
Journal of neuroimmunology, 261(1-2), 134-140 (2013-06-27)
The role of cis-urocanic acid (UCA) as a UV-mediated immunomodulator in MS patients was investigated. Plasma levels of cis-UCA were significantly lower in MS patients compared to controls. Stimulation of MBP- and MOG-specific T cells in the presence of cis-UCA
S Beissert et al.
Journal of immunology (Baltimore, Md. : 1950), 167(11), 6232-6238 (2001-11-21)
UV radiation induces skin cancer primarily by its DNA-damaging properties, but also by its capacity to suppress the immune system. The photoisomer of urocanic acid (UCA), cis-UCA, is an important mediator of UV-induced immunosuppression and is involved in the inhibition
Hanna-Mari Jauhonen et al.
Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie, 255(12), 2357-2362 (2017-08-26)
Our purpose was to investigate the effect of locally administered cis-urocanic (cis-UCA) in two experimental models of allergic conjunctivitis. The compound 48/80 (C48/80)-induced ocular irritation model (IgE-independent) and the ovalbumin (OA)-induced ocular allergy model (IgE-mediated) were used to test and
Amy A Irving et al.
BMC neuroscience, 18(1), 8-8 (2017-01-07)
Ultraviolet B irradiation confers strong resistance against experimental autoimmune encephalomyelitis, a model of multiple sclerosis. This protection by ultraviolet B is independent of vitamin D production but causes isomerization of urocanic acid, a naturally occurring immunosuppressant. To determine whether UCA
Evgeny Berdyshev et al.
The Journal of allergy and clinical immunology, 147(1), 361-367 (2020-07-03)
The nonlesional skin of children with atopic dermatitis (AD) with peanut allergy (PA) is associated with increased transepidermal water loss; low urocanic acid (UCA) and pyrrolidone carboxylic acid (PCA), both of which are filaggrin breakdown products; and a reduced ratio

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