(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

• ChemBase编号: 2977
• 分子式: C15H12O4
• 平均质量: 256.25338
• 单一同位素质量: 256.07355886
• SMILES: Oc1ccc(cc1)/C=C/C(=O)c1ccc(O)cc1O
• Canonical SMILES: Oc1ccc(cc1)/C=C/C(=O)c1ccc(cc1O)O
• InChI: InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
• InChIKey: DXDRHHKMWQZJHT-FPYGCLRLSA-N

名称和登记号

名称

• IUPAC标准名: (2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• IUPAC传统名: isoliquiritigenin
• 别名: 2',4,4'-三羟基查耳酮; 2',4,4'-Trihydroxychalcone; Isoliquiritigenin; Isoliquiritigenin; 2',4,4'-Trihydroxychalcone; (E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one; 4,2′,4′-Trihydroxychalcone; Isoliquiritigenin; ISL; 2',4,4'-Trihydroxychalcone; GU 17; (2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

登记号

• CAS号: 961-29-5
• MDL号: MFCD00075907
• PubChem SID: 24278037; 46506198; 160966424
• PubChem CID: 638278

理论计算性质

JChem

• Acid pKa: 7.1109757
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 3.6191914
• LogD (pH = 7.4): 3.1476436
• Log P: 3.6296294
• 摩尔折射率: 72.8197 cm^3
• 极化性: 27.143188 Å^3
• 极化表面积: 77.76 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.04
• LOG S: -3.67
• 溶解度: 5.51e-02 g/l

分子性质

理化性质

• 溶解度: DMSO: soluble20 mg/mL; H2O: <0.1 mg/mL; methanol: soluble10 mg/mL
• 外观: Orange powder; yellow to orange powder
• 熔点: 185-187°C

安全信息

• 保存条件: -20°C
• 保存注意事项: Light Sensitive & Hygroscopic
• RTECS编号: FL7080000
• 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: 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: rat ... Alox5(25290)

产品相关信息

• 纯度: 97%
• 成盐信息: Free Base

详细说明

DrugBank - DB03285

Drug information: experimental

Selleck Chemicals - S2404

Research Area: Cancer
Biological Activity:
Isoliquiritigenin (GU 17) is a strong nod gene- and glyceollin resistance-inducing flavonoid from soybean root exudate. Isoliquiritigenin (GU 17) is a licorice chalcone, a type of flavonoid. Isoliquiritigenin (GU 17)  is currently under experimentation phase testing for use as a cancer treatment as well as an aide for cocaine addiction. Isoliquiritigenin (GU 17)  is a sirtuin-activating compound. The ability of isoliquiritigenin (GU 17) to suppress metastasis was examined in a pulmonary metastasis model of mouse renal cell carcinoma. Isoliquiritigenin (GU 17) significantly reduced pulmonary metastasis, without any weight loss or leukocytopenia. Isoliquiritigenin (GU 17) suppressed in vitro proliferation of carcinoma cells, potentiated nitric oxide production by lipopolysaccharide-stimulated macrophages, and facilitated cytotoxicity of splenic lymphocytes in vitro. [1][2]

Sigma Aldrich - I3766

Biochem/physiol Actions
Soluble guanylyl cyclase activator. Possesses antitumor activity.
Caution
Photosensitive, hygroscopic
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. I3766.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - I820850

Isoliquiritigenin (ISL) is a flavonoid found in licorice root and several other plants that displays antioxidant, anti-inflammatory, and antitumor activities as well as hepatoprotection against steatosis-induced oxidative stress. ISL induces quinone reduc

参考文献

• Yamazaki S et al. Cancer Lett. 2002 Sep 8;183(1):23-30.
• Agrawal, R., et al.: Food Chem. Toxicol., 36, 975 (1998)
• Baba, M., et al.: Biol. Pharm. Bull., 25, 247 (1998)
• Chowdhury, S., et al.: Anticancer Res., 25, 2055 (1998)