2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

• ChemBase编号: 105695
• 分子式: C17H16O4
• 平均质量: 284.30654
• 单一同位素质量: 284.10485899
• SMILES: Oc1c(O)cc(/C=C/C(=O)OCCc2ccccc2)cc1
• Canonical SMILES: O=C(/C=C/c1ccc(c(c1)O)O)OCCc1ccccc1
• InChI: InChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2
• InChIKey: SWUARLUWKZWEBQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate; 2-phenylethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• IUPAC传统名: 2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate; caffeic acid phenethyl ester
• 别名: Caffeic acid phenethyl ester(CAPE); 3-(3,4-Dihydroxyphenyl)-2-propenoic Acid 2-Phenylethyl Ester; Phenethyl caffeate; PHENYLETHYL CAFFEATE; CAPE; CAFFEIC ACID PHENETHYL ESTER; Caffeic acid phenethyl ester; Phenylethyl caffeate; Caffeic acid 2-phenylethyl ester; β-Phenylethyl caffeate; Phenethyl 3-(3,4-dihydroxyphenyl)acrylate

登记号

• CAS号: 104594-70-9
• MDL号: MFCD00866470
• PubChem SID: 24278341; 162092374
• PubChem CID: 5281787
• Chemspider ID: 4445100
• 维基百科标题: Caffeic_acid_phenethyl_ester

理论计算性质

• Acid pKa: 9.208643
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.921233
• LogD (pH = 7.4): 3.9146662
• Log P: 3.9213173
• 摩尔折射率: 81.1584 cm^3
• 极化性: 30.931627 Å^3
• 极化表面积: 66.76 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble; Ethanol; ethanol: soluble; Ethyl Acetate; ethyl acetate: soluble50 mg/mL
• 外观: off-white powder; Off-White Solid

安全信息

• 保存条件: -20°C; 2-8°C; protect from light
• RTECS编号: UD3334375
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

药理学性质

• 作用靶点: NF-κB
• 相关基因信息: human ... NFKB2(4791)

产品相关信息

• 纯度: ≥97%; ≥97% (HPLC); 98%
• 成盐信息: Free Base

详细说明

MP Biomedicals - 02193775

A cytotoxic agent to cancer cell lines. Acts as an inhibitor of protein tyrosine kinase and ornithine decarboxylase.

MP Biomedicals - 02195860

Purity: >97%
Active component of propolis from honeybee hives. Possesses anti-viral, anti-inflammatory and immunomodulary properties. Inhibits growth of several types of transformed cells and induces apoptosis in cloned rat embryo fibroblast (CREF) cells.

Sigma Aldrich - C8221

Biochem/physiol Actions
Caffeic acid phenethyl ester is a specific inhibitor of the nuclear transcription factor NF-κB.
Application
Caffeic acid phenethyl ester (CAPE) is the active component of propolis, a honeybee hive product.1 Caffeic acid phenethyl ester is a specific inhibitor of the nuclear transcription factor, NF-κB.2 CAPE has been shown to significantly suppress the lipoxygenase pathway of arachidonic acid metabolism during inflammation.3,4 Caffeic acid phenethyl ester inhibits HIV-1 integrase,5,6 and also inhibits proliferation of transformed cells.7,8 It induces apoptosis in transformed fibroblasts,9 and interferes with EGF signal transduction affecting both protein kinase C and ornithine decarboxylase activity.7

Toronto Research Chemicals - C080050

Cytotoxic agent against cancer cell lines. Inhibitor of ornithine decarboxylase and protein tyrosine kinase. Found to be a specific inhibitor of the nuclear transcription factor, NF-kB. It has also been shown to significantly suppress the lipoxygenase p

参考文献

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• Fesen, M.R., et al.: Biochem. Pharmacol., 48, 595 (1988)
• Su, Z.Z., et al.: Cancer Res., 54, 1865 (1988)
• Zheng, Z.S., et al.: Oncol. Res., 7, 445 (1988)
• Mirzoeva, O.K. and Calder, P.C.: Essent. Fatty