(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

• ChemBase编号: 130198
• 分子式: C21H22O5
• 平均质量: 354.39638
• 单一同位素质量: 354.1467238
• SMILES: O=C(c1c(OC)cc(O)c(c1O)CC=C(C)C)/C=C/c1ccc(O)cc1
• Canonical SMILES: COc1cc(O)c(c(c1C(=O)/C=C/c1ccc(cc1)O)O)CC=C(C)C
• InChI: InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3
• InChIKey: ORXQGKIUCDPEAJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one; 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• IUPAC传统名: xanthohumol; 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• 别名: 黄腐醇 来源于啤酒花 (Humulus lupulus); (E)-1-[2,4-二羟基-6-甲氧基-3-(3-甲基-2-丁烯基)苯基]-3-(4-羟基苯基)丙烯酮; 2′,4,4′-三羟基-6′-甲氧基-3′-异戊烯基查耳酮; 黄腐醇; Xanthohumol from hop (Humulus lupulus); 2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone; Desmethylxanthohumol; Xanthohumol; (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone; 2′,4,4′-Trihydroxy-6′-methoxy-3′-prenylchalcone; Xanthohumol

登记号

• CAS号: 6754-58-1; 569-83-5
• MDL号: MFCD00210576
• PubChem SID: 162224482; 24902121
• PubChem CID: 639665
• CHEMBL: 253896
• Chemspider ID: 555077
• 美国药典/FDA物质标识码: T4467YT1NT
• 维基百科标题: Xanthohumol

理论计算性质

• Acid pKa: 7.010896
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 5.187427
• LogD (pH = 7.4): 4.6460238
• Log P: 5.2005253
• 摩尔折射率: 103.5257 cm^3
• 极化性: 38.62526 Å^3
• 极化表面积: 86.99 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: soluble25 mg/mL; ethanol: soluble10 mg/mL
• 外观: Orange powder; powder

安全信息

• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3077
• 德国WGK号: 3
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 43-50/53
• 安全公开号: 22-45-60-61
• GHS危险品标识: GHS07; GHS09
• GHS警示词: Warning
• GHS危险声明: H317-H400
• GHS警示性声明: P273-P280
• 个人保护装置: Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥96% (HPLC); 99.0
• 级别: primary reference standard
• Empirical Formula (Hill Notation): C21H22O5

详细说明

Sigma Aldrich - X0379

Biochem/physiol Actions
Prenylated flavonoids such as xanthohumol have antiproliferative and cytotoxic effects in human cancer cell lines1. Xanthohumol protected HepG2 cells against benzo[a]pyrene and related carcinogens. It also protected against reactive oxygen species (ROS), not by a direct anti-oxidant effect, but instead mediated by induction of cellular defense mechanisms against oxidative stress.2Xanthohumol inhibits diacylglycerol acetyltransferase (DGAT)3 and human P450 enzymes4. It also inhibits the expression of HIF-1α and VEGF under hypoxic conditions5.
Protocols & Applications
Hops (Humulus lupulus) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - 01130595

Application
草药产品分析的标准品。
General description
由 HWI Analytik 生产和检验 证书上注明了由定量 NMR 确定的准确含量