1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

• ChemBase编号: 81908
• 分子式: C21H20O6
• 平均质量: 368.3799
• 单一同位素质量: 368.12598836
• SMILES: O=C(/C=C/c1ccc(c(c1)OC)O)CC(=O)/C=C/c1cc(c(cc1)O)OC
• Canonical SMILES: COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(c(c2)OC)O)ccc1O
• InChI: InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3
• InChIKey: VFLDPWHFBUODDF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione; (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• IUPAC传统名: turmeric; curcumin; (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 别名: 姜黄素; Curcumin; Natural Yellow3; (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione; (E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione; Diferulylmethane; Curcumin; Diferuloylmethane; C.I. 75300; Natural Yellow 3; Curcumin; Curcuminoid; 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione; Curcuma yellow; (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione; C Yellow 15; C.I. Natural Yellow 3; Curcuma; Curcumin I; Curcumine; Haidr; Halad; Haldar; Ukon

登记号

• CAS号: 458-37-7
• EC号: 207-280-5
• MDL号: MFCD00008365
• Beilstein号: 2306965
• 默克索引号: 142673
• PubChem SID: 24892408; 24892983; 162069027
• PubChem CID: 969516
• CHEBI ID: 3962
• CHEMBL: 116438
• Chemspider ID: 839564
• 美国药典/FDA物质标识码: IT942ZTH98
• 维基百科标题: Curcuminoid; Curcumin
• Color Index Number: 75300
• E编码: E100

理论计算性质

• Acid pKa: 9.061334
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 4.124406
• LogD (pH = 7.4): 4.1151395
• Log P: 4.1245246
• 摩尔折射率: 103.8106 cm^3
• 极化性: 38.873188 Å^3
• 极化表面积: 93.06 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 0.5 M NaOH: soluble (then immediately dilute in PBS); Chloroform; DMSO; DMSO: >11 mg/mL; ethanol: soluble10 mg/mL
• 外观: Bright Orange Solid; Bright Yellow; to orange powder; Bright yellow-orange powder; orange powder
• 熔点: 162-163°C; 170-175°C; 175-180 °C; 183°C
• 蒸汽密度: 13 (vs air)

安全信息

• 保存条件: Refrigerator
• 保存注意事项: Irritant
• RTECS编号: MI5230000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2; 3
• 危险公开号: 36/37/38
• 安全公开号: 26; 26-36; 26-36/37; 26-36/37/39
• TSCA收录: 是
• 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; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 保存温度: -20°C; 2-8°C

药理学性质

• 相关基因信息: human ... APP(351), CYP1A2(1544)
• 生物活性机理: Acts as a free radical scavenger and antioxidant, inhibiting lipid peroxidation and oxidative DNA damage; Induce glutathione S-transferase and are potent inhibitors of cytochrome P450;; Inhibitor of eicosanoid biosynthesis

产品相关信息

• 纯度: ~70% (HPLC); ≥95.0% (TLC); ≥98.0% (HPLC); 95% (total curcuminoid content), from Turmeric rhizome
• 级别: analytical standard
• 简要说明: Tautomers
• 生物来源: from Curcuma longa (Turmeric); Isol. from Curcuma zedoaria (turmeric), other Curcuma spp. and other spp.
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antiamyloid; Antiarthritic; Antiinflammatory agent; Antitumor; Bile stimulant showing hepatoprotective props; Possesses bactericidal and fungicidal props.
• 线性分子式: [HOC6H3(OCH3)CH=CHCO]2CH2

详细说明

InterBioScreen - BB_NC-1422

Tautomers

Toronto Research Chemicals - C838500

A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and antioxidant properties. Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory

Sigma Aldrich - C1386

Biochem/physiol Actions
A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and anti-oxidant properties. Curcumin has been cited as a potential chemopreventive agent, in addition to its chemotherapeutic activity.1 Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IκB kinase. Inhibits inducible nitric oxide synthase (iNOS), cycloxygenase and lipoxygenase. Easily penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nuclear envelope.

Sigma Aldrich - 28260

Biochem/physiol Actions
A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and anti-oxidant properties. Curcumin has been cited as a potential chemopreventive agent, in addition to its chemotherapeutic activity.1 Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IκB kinase. Inhibits inducible nitric oxide synthase (iNOS), cycloxygenase and lipoxygenase. Easily penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nuclear envelope.

Sigma Aldrich - 08511

Biochem/physiol Actions
A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and anti-oxidant properties. Curcumin has been cited as a potential chemopreventive agent, in addition to its chemotherapeutic activity.1 Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IκB kinase. Inhibits inducible nitric oxide synthase (iNOS), cycloxygenase and lipoxygenase. Easily penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nuclear envelope.

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