(2Z)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid

• ChemBase编号: 131567
• 分子式: C8H10O4
• 平均质量: 170.1626
• 单一同位素质量: 170.0579088
• SMILES: CC(=C)C(=O)/C(=C/C(=O)O)/OC
• Canonical SMILES: CO/C(=C\C(=O)O)/C(=O)C(=C)C
• InChI: InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4-
• InChIKey: VOUGEZYPVGAPBB-XQRVVYSFSA-N

名称和登记号

名称

• IUPAC标准名: (2Z)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid; 3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid
• IUPAC传统名: penicillic acid
• 别名: 3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid; PA; Penicillic acid

登记号

• CAS号: 90-65-3
• EC号: 202-008-1
• MDL号: MFCD00004365
• PubChem SID: 162225845
• PubChem CID: 1268111

理论计算性质

• Acid pKa: 3.2046993
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -1.2381535
• LogD (pH = 7.4): -2.4098883
• Log P: 1.0347244
• 摩尔折射率: 43.8815 cm^3
• 极化性: 16.329432 Å^3
• 极化表面积: 63.6 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >10 mg/mL; H2O: ≤10 mg/mL
• 外观: white

安全信息

• RTECS编号: MM2625000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C8H10O4

详细说明

Sigma Aldrich - P0063

Application
Penicillic acid is a polyketide mycotoxin produced by several species of Aspergillus and Penicillium species. It is used to study FasL-induced apoptosis and cell viability in Burkitt′s lymphoma Raji cells1. It is used to study bacterial bioluminescence bioassays2 and genotoxicity of hepatocytes3.
Biochem/physiol Actions
Penicillic acid induces single and double strand DNA breaks. Penicillic acid irreversibly inhibits GDP-mannose dehydrogenase (DMG), an alginate synthesis enzyme. It also inhibits muscle aldose dehydrogenase, alcohol dehydrogenase, and lactate dehydrogenase. Penicillic acid inhibits fas ligand-induced apoptosis by blocking self-processing of caspase-8 in death-inducing signaling complex1.
Penicillic acid is a polyketide mycotoxin produced by several species of Aspergillus and Penicillium species. It induces single and double strand DNA breaks. Penicillic acid irreversibly inhibits GDP-mannose dehydrogenase (DMG), an alginate synthesis enzyme. It also inhibits muscle aldose dehydrogenase, alcohol dehydrogenase, and lactate dehydrogenase.

Sigma Aldrich - P1514

Biochem/physiol Actions
Penicillic acid is a polyketide mycotoxin produced by several species of Aspergillus and Penicillium species. It induces single and double strand DNA breaks. Penicillic acid irreversibly inhibits GDP-mannose dehydrogenase (DMG), an alginate synthesis enzyme. It also inhibits muscle aldose dehydrogenase, alcohol dehydrogenase, and lactate dehydrogenase.