1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

• ChemBase编号: 72916
• 分子式: C15H10O5
• 平均质量: 270.2369
• 单一同位素质量: 270.05282342
• SMILES: c12c(cc(cc1O)CO)C(=O)c1c(C2=O)c(ccc1)O
• Canonical SMILES: OCc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
• InChI: InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2
• InChIKey: YDQWDHRMZQUTBA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione
• IUPAC传统名: 1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione; aloe emodin
• 别名: Aloe emodin; 1,8-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione; Aloe-emodin; Aloeemodin; Aloe emodin; 1,8-Dihydroxy-3-hydroxymethylanthraquinone; Aloeemodin; Aloe-emodin; 1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione; 3-Hydroxymethylchrysazin; Aloe-emodol; NSC 38628; Rhabarberone; 1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone; 3-Hydroxymethylchrysazine; Aloe-emodin

登记号

• CAS号: 481-72-1
• EC号: 207-571-7
• MDL号: MFCD00017373
• Beilstein号: 2059062
• PubChem SID: 162037836; 24891267
• PubChem CID: 10207
• CHEMBL: 40275
• Chemspider ID: 9792
• KEGG ID: C10294
• 维基百科标题: Aloe_emodin

理论计算性质

• Acid pKa: 7.8008704
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 2.842074
• LogD (pH = 7.4): 2.689786
• Log P: 2.8442256
• 摩尔折射率: 71.9287 cm^3
• 极化性: 26.999968 Å^3
• 极化表面积: 94.83 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform
• 外观: Orange Solid; Yellow powder
• 熔点: 223-224 °C (433.4-435.2°F) (Sublimes in CO₂ stream); 223-224°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: CB6712200
• 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: 2-8°C

药理学性质

• 给药途径: Oral
• 生物活性机理: Apoptosis inducer; Caspase-3 activator; Caspase-8 activator; Caspase-9 activator;; Protein kinase C (PKC) inhibitor

产品相关信息

• 纯度: ≥95% (HPLC); ≥97.0% (HPLC)
• 级别: analytical standard
• 成盐信息: Free Base
• 生物来源: Present in aloe latex, an exudate from the aloe plant
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antibacterial; Antileukaemic; Antimicrobial; Antimutagenic; Antiseptic; Antitumor; Cathartic
• Empirical Formula (Hill Notation): C15H10O5

详细说明

Selleck Chemicals - S2259

Related research area: Infection

InterBioScreen - BB_NC-2562

Rheum palmatum L.

Sigma Aldrich - A7687

Biochem/physiol Actions
Laxative/cathartic compound; increases the contraction of intestinal smooth muscle by releasing endogenous acetylcholine. Anti-tumor activity is associated with an increased production of reactive oxygen species (ROS) that, in turn, reduces the mitochondrial transmembrane electrical potential, thus inducing a permeability transition that sets in motion a series of events culminating in cellular apoptosis. Genotoxicity and mutagenicity appear to be due to the inhibition of topoisomerase II activity by aloe emodin.

Sigma Aldrich - 93938

Biochem/physiol Actions
Laxative/cathartic compound; increases the contraction of intestinal smooth muscle by releasing endogenous acetylcholine. Anti-tumor activity is associated with an increased production of reactive oxygen species (ROS) that, in turn, reduces the mitochondrial transmembrane electrical potential, thus inducing a permeability transition that sets in motion a series of events culminating in cellular apoptosis. Genotoxicity and mutagenicity appear to be due to the inhibition of topoisomerase II activity by aloe emodin.

Toronto Research Chemicals - A575400

Shows significant inhibitory activity against the P-388 leukemia in mice when administered as a suspension in acetone-Tween 80. Has a specific in vitro and in vivo antineuroectodermal tumor activity. Cathartic.

参考文献

• http://en.wikipedia.org/wiki/Aloe_emodin
• Hung, K., et al.: J. Exp. Med., 188, 2357 (1998)
• Gazzola, P.T., et al.: Cancer Res., 60, 2800 (1998)
• Irie, T., et al.: Int. J. Cancer, 121, 8784 (1998)
• Zhao, J., et al.: Eur. J. Neurol., 14, 510 (1998)
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