methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

• ChemBase编号: 105102
• 分子式: C10H10O4
• 平均质量: 194.184
• 单一同位素质量: 194.0579088
• SMILES: COC(=O)/C=C/c1c(O)ccc(O)c1
• Canonical SMILES: COC(=O)/C=C/c1cc(O)ccc1O
• InChI: InChI=1S/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3
• InChIKey: BQCNSTFWSKOWMA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate; methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate
• IUPAC传统名: methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate; methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate
• 别名: Erbstatin analog; 2,5-Dihydroxycinnamic acid methyl ester; Methyl 2,5-dihydroxycinnamate; ERBSTATIN ANALOG; 3-(2,5-Dihydroxyphenyl)-2-propenoic Acid Methyl Ester; Methyl 2,5-Dihydroxycinnamate

登记号

• CAS号: 63177-57-1
• MDL号: MFCD00132932
• PubChem SID: 162092521; 24893707
• PubChem CID: 5353609

理论计算性质

• Acid pKa: 9.48247
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.908138
• LogD (pH = 7.4): 1.9046254
• Log P: 1.908183
• 摩尔折射率: 51.7908 cm^3
• 极化性: 19.525108 Å^3
• 极化表面积: 66.76 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 0.1 M NaOH: soluble; H2O: insoluble; Methanol; methanol: soluble
• 外观: Pale Yellow Solid; yellow crystalline
• 熔点: 178-180°C

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 23/24/25-36/37/38
• 安全公开号: 22-26-36-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H311-H315-H319-H331-H335
• GHS警示性声明: P261-P280-P301 + P310-P305 + P351 + P338-P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• 保存温度: -20°C

产品相关信息

• 纯度: >98%; ≥95%

详细说明

MP Biomedicals - 02158813

Purity: >98%
Erbstatin is a novel inhibitor of the EGF receptor associated tyrosine kinase^1 . It is an unstable compound and is completely inactivated in serum in 30 minutes. Methyl 2,5-dihydroxycinnamate is a stable erbstatin analog retaining activity after a 60 minute incubation. It inhibits EGF receptor associated tyrosine kinase in vitro (IC₅₀ =0.77 μM)^2 . Inhibition is competitive with substrate and noncompetitive with ATP.

Sigma Aldrich - D2667

Biochem/physiol Actions
Inhibitor of EGF receptor-associated tyrosine kinase.
Caution
Photosensitive.
Linkage
Stable analog of erbstatin.

Toronto Research Chemicals - M302700

A stable Erbstatin analogue that inhibits tyrosine kinase. Shown to delay the S-phase induction by epidermal growth factor in quiescent normal rat kidney cells, without affecting the total amount of DNA synthesis.

参考文献

• Imoto, M., et al., Biochem. Int. , 15 : 989 (1987).
• Umezawa, K., et al., FEBS Lett. , 260 : 198 (1990).
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• Zhou, G., et al.: J. Clin. Invest., 108, 1167 (2000)
• Reznick, R., et al.: J. Physiol., 574, 33 (2000)