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

• ChemBase ID: 131567
• Molecular Formular: C8H10O4
• Molecular Mass: 170.1626
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid; 3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid
• IUPAC Traditional name: penicillic acid
• Synonyms: 3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid; PA; Penicillic acid

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.2046993
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.2381535
• LogD (pH = 7.4): -2.4098883
• Log P: 1.0347244
• Molar Refractivity: 43.8815 cm^3
• Polarizability: 16.329432 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: ≤10 mg/mL
• Apperance: white

Safety Information

• RTECS: MM2625000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

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

DETAILS

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.