icosa-8,11,14-trien-5-ynoic acid

• ChemBase ID: 104053
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: CCCCC/C=C/C/C=C/C/C=C/CC#CCCCC(=O)O
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/CC#CCCCC(=O)O
• InChI: InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14,17-19H2,1H3,(H,21,22)
• InChIKey: GIOQWSLKUVKKAO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: icosa-8,11,14-trien-5-ynoic acid
• IUPAC Traditional name: icosa-8,11,14-trien-5-ynoic acid
• Synonyms: 5,6-dehydro AA; cis-8,11,14-Eicosatrien-5-ynoic acid; 5,6-Dehydroarachidonic acid; 5,6-DEHYDROARACHIDONIC ACID

Database IDs

• CAS Number: 58688-54-3
• MDL Number: MFCD00065715
• PubChem SID: 24893642; 162091575
• PubChem CID: 5353350

CALCULATED PROPERTIES

• Acid pKa: 4.483154
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.4783974
• LogD (pH = 7.4): 3.7112458
• Log P: 6.533799
• Molar Refractivity: 98.1988 cm^3
• Polarizability: 36.279404 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: ethanol solution
• Flash Point: 17 °C; 62 °F

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Flammable (F)
• UN Number: 1170
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-16
• Safety Statements: 16
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%; 95%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C20H30O2

DETAILS

MP Biomedicals - 02154279

Purity: 95% Solution in ethanol. Selective, irreversible inhibitor of 5-lipoxygenase.

Sigma Aldrich - D2154

Biochem/physiol Actions
Inhibits 5-lipoxygenase of guinea pig leukocytes with an IC50 of 10 μM. In extracts of rat basophilic leukemia cells preincubated with 5,6-dehydro AA, the Ki for the conversion of arachidonic acid to 5-HPETE is 15 μM.
General description
An analog of arachidonic acid in which the 5,6 double bond has been replaced with an acetylene group.