(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoic acid

• ChemBase ID: 4125
• Molecular Formular: C20H32O2
• Molecular Mass: 304.46688
• Monoisotopic Mass: 304.24023026
• SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O
• InChI: InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6+,10-9+,13-12+,16-15+
• InChIKey: YZXBAPSDXZZRGB-CGRWFSSPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoic acid; icosa-5,8,11,14-tetraenoic acid
• IUPAC Systematic name: (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid
• IUPAC Traditional name: arachidonic acid
• Synonyms: Arachidonic acid; Immunocytophyte; cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid; Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid; Arachidonic Acid; 5,8,11,14-Eicosatetraenoic Acid; 5,8,11,14-all-cis-Eicosatetraenoic acid; all-cis-5,8,11,14-Eicosatetraenoic acid; Arachidonate; 花生四烯酸; 二十碳-5Z,8Z,11Z,14Z-四烯酸; 全顺式-5,8,11,14-二十碳四烯酸

Database IDs

• CAS Number: 506-32-1
• EC Number: 208-033-4
• MDL Number: MFCD00004417
• Beilstein Number: 1713889
• PubChem SID: 46506683; 24846907; 160967557
• PubChem CID: 5312542; 444899
• CHEBI ID: 36306
• CHEMBL: 15594
• Chemspider ID: 392692
• DrugBank ID: DB04557
• KEGG ID: C00219
• MeSH Name: Arachidonic+acid
• Unique Ingredient Identifier: 27YG812J1I
• Wikipedia Title: Arachidonic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.819772
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.8251953
• LogD (pH = 7.4): 4.052063
• Log P: 6.5871706
• Molar Refractivity: 99.954 cm^3
• Polarizability: 37.14881 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.8
• LOG S: -6.3
• Solubility (Water): 1.51e-04 g/l

PROPERTIES

Physical Property

• Apperance: liquid
• Melting Point: -49 °C(lit.); -49°C
• Boiling Point: 169 - 171°C (at 0.15 mmHg); 169-171 °C/0.15 mmHg(lit.); 170°C @ 0.2 mm Hg
• Flash Point: 113 °C; 113°C (235.4°F); 235.4 °F
• Density: 0.922 g/cm^3; 0.922 g/ml; 0.922 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4872(lit.)
• Partition Coefficient: 6.994
• pKa: 4.752

Safety Information

• Storage Condition: 0°C, Desiccate, Protect from light; 0°C, Protect from light
• RTECS: CE6675000
• German water hazard class: 3
• Risk Statements: 19; R19
• NFPA704:
  

  1

  1

  0
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%; >95.0% (GC); ≥98.5% (GC); 90-95%; 99%
• Grade: puriss.
• Biological Source: from non-animal source
• Quality Level: PREMIUM
• Shipped in: dry ice
• Linear Formula: CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H

DETAILS

MP Biomedicals - 02194625

Cell Culture Reagent
Purity: 99%
Clear, colorless liquid which may develop a yellowish cast.

MP Biomedicals - 02100269

Purity: 90-95%

MP Biomedicals - 02150384

Purity: >98%
Clear, colorless liquid which may develop a yellowish cast.
Activates protein kinase C

DrugBank - DB04557

• Drug Groups: experimental
• Description: An unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. [PubChem]

Sigma Aldrich - A3611

Packaging
Sealed ampule
Biochem/physiol Actions
Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Sigma Aldrich - 10931

Packaging
1 g in glass bottle
250 mg in glass bottle
Biochem/physiol Actions
Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Sigma Aldrich - 233846

Other Notes
See Chem. Eng. News., 61(33), 2 (1983).
Biochem/physiol Actions
Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Sigma Aldrich - 10929

Other Notes
Precursor of many potent biological mediators such as prostaglandins, thromboxanes, leukotrienes. Role of arachidonic acid in the metabolism of platelet-activating factor (PAF)1
Biochem/physiol Actions
Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .