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

• ChemBase ID: 132964
• 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-DOFZRALJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
• IUPAC Traditional name: arachidonic acid
• Synonyms: Arachidonic Acid, >90% Technical Grade; (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid; (all-Z)-5,8,11,14-Eicosatetraenoic Acid; 5,8,11,14-all-cis-Eicosatetraenoicmmunocytophyte; all-cis-5,8,11,14-Eicosatetraenoic Acid; cis-5,8,11,14-Eicosatetraenoic Acid; Arachidonic Acid, 99%; Immunocytophyte; Arachidonic acid; 二十碳-5Z,8Z,11Z,14Z-四烯酸; 全顺式-5,8,11,14-二十碳四烯酸; 花生四烯酸

Database IDs

• CAS Number: 506-32-1
• EC Number: 208-033-4
• MDL Number: MFCD00004417
• Beilstein Number: 1713889
• PubChem SID: 24891487; 24890784; 162227241; 24890733
• PubChem CID: 444899

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: absolute ethanol: soluble10 mg/mL; Chloroform; Dichloromethane; ethanol: ≥10 mg/mL; ethanol: ≥10 mg/mL (lit.); Hexane
• Apperance: clear colorless to very faintly yellow liquid; colorless to light yellow liquid; Colourless to Light Yellow Oil
• Melting Point: -49 °C(lit.)
• Boiling Point: 161-171°C @0.15 torr; 169-171 °C/0.15 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 0.922 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4872(lit.)

Safety Information

• Storage Condition: -86°C Freezer
• RTECS: CE6675000
• German water hazard class: 3
• Risk Statements: 19
• 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: ≥85% (capillary GC); ≥99% (GC)
• Suitability: suitable for cell culture
• Biological Source: from porcine liver
• Shipped in: dry ice

DETAILS

Sigma Aldrich - A3925

Biochem/physiol Actions
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
花生四烯酸 (AA) 是一种 ω6 不饱和脂肪酸，是细胞膜磷脂的组分。在炎症反应中，水解磷脂酶 A2 可将 AA 从膜磷脂中释放出来。然后，AA 可被至少两种环加氧酶 (COX) 亚型代谢为前列腺素和血栓烷，被脂氧合酶代谢为白三烯和脂氧素，以及通过细胞色素 p450 催化代谢为环氧-二十碳三烯酸。AA 及其代谢产物在多种生物过程中发挥着重要作用，包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化，以及细胞凋亡。已证实 AA 可与 G 蛋白的亚基结合，抑制 Ras GTP 酶激活蛋白 (GAP) 的活性。AA 的细胞摄取需要消耗能量并涉及跨细胞质膜的蛋白质辅助运输。

Sigma Aldrich - A3555

包装
Sealed ampule.
Biochem/physiol Actions
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
花生四烯酸 (AA) 是一种 ω6 不饱和脂肪酸，是细胞膜磷脂的组分。在炎症反应中，水解磷脂酶 A2 可将 AA 从膜磷脂中释放出来。然后，AA 可被至少两种环加氧酶 (COX) 亚型代谢为前列腺素和血栓烷，被脂氧合酶代谢为白三烯和脂氧素，以及通过细胞色素 p450 催化代谢为环氧-二十碳三烯酸。AA 及其代谢产物在多种生物过程中发挥着重要作用，包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化，以及细胞凋亡。已证实 AA 可与 G 蛋白的亚基结合，抑制 Ras GTP 酶激活蛋白 (GAP) 的活性。AA 的细胞摄取需要消耗能量并涉及跨细胞质膜的蛋白质辅助运输。

Sigma Aldrich - A9673

包装
1 g in ampule
10, 50, 100, 500 mg in ampule
Sealed ampule
Biochem/physiol Actions
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
花生四烯酸 (AA) 是一种 ω6 不饱和脂肪酸，是细胞膜磷脂的组分。在炎症反应中，水解磷脂酶 A2 可将 AA 从膜磷脂中释放出来。然后，AA 可被至少两种环加氧酶 (COX) 亚型代谢为前列腺素和血栓烷，被脂氧合酶代谢为白三烯和脂氧素，以及通过细胞色素 p450 催化代谢为环氧-二十碳三烯酸。AA 及其代谢产物在多种生物过程中发挥着重要作用，包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化，以及细胞凋亡。已证实 AA 可与 G 蛋白的亚基结合，抑制 Ras GTP 酶激活蛋白 (GAP) 的活性。AA 的细胞摄取需要消耗能量并涉及跨细胞质膜的蛋白质辅助运输。

Toronto Research Chemicals - A765001

Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats,

Toronto Research Chemicals - A765000

Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats,

REFERENCES

• Kurosawa, T., et al.: J. Cell. Physiol., 219, 606 (2009)
• Mazalli, M., et al.: J. Agric. Food Chem., 57, 5028 (2009)
• Kurosawa, T., et al.: J. Cell. Physiol., 219, 606 (2009)
• Mazalli, M., et al.: J. Agric. Food Chem., 57, 5028 (2009)