icosa-5,8,11,14-tetraynoic acid

• ChemBase ID: 103365
• Molecular Formular: C20H24O2
• Molecular Mass: 296.40336
• Monoisotopic Mass: 296.17763001
• SMILES: CCCCCC#CCC#CCC#CCC#CCCCC(=O)O
• Canonical SMILES: CCCCCC#CCC#CCC#CCC#CCCCC(=O)O
• InChI: InChI=1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)
• InChIKey: MGLDCXPLYOWQRP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: icosa-5,8,11,14-tetraynoic acid
• IUPAC Traditional name: icosa-5,8,11,14-tetraynoic acid
• Synonyms: 5,8,11,14-Eicosatetraynoic acid; ETYA; Octadehydroarachidonic acid; 5,8,11,14-EICOSATETRAYNOIC ACID

Database IDs

• CAS Number: 1191-85-1
• MDL Number: MFCD00036967
• Beilstein Number: 1798411
• PubChem SID: 162090937; 24894432
• PubChem CID: 1780

CALCULATED PROPERTIES

• Acid pKa: 4.0834813
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.9441676
• LogD (pH = 7.4): 3.2644348
• Log P: 6.373684
• Molar Refractivity: 92.9332 cm^3
• Polarizability: 33.68693 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 79-81 °C

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... ALOX15(246)

Product Information

• Purity: ≥97%; ≥97.0% (HPLC); 98%
• Empirical Formula (Hill Notation): C20H24O2

DETAILS

MP Biomedicals - 02151508

Supplied as a white solid
Purity: 98%
Archidonic acid, cyclooxygenase, lipoxygenase, and cytochrome P450 inhibitor.

Sigma Aldrich - E1768

Biochem/physiol Actions
Cyclooxygenase and lipoxygenase inhibitor.

Sigma Aldrich - 44870

Biochem/physiol Actions
Cyclooxygenase and lipoxygenase inhibitor.
Other Notes
Acetylenic analogue of arachidonic acid. Inhibits lipoxygenases and protaglandin synthetase1; cyclooxygenase2; and lipoxygenase3,4

REFERENCES

• Salari, H., et al., Prostagland. Leukotrienes Med., 13: 53 (1984).