Arachidonic acid - CAS 506-32-1
Catalog: |
BB027150 |
Product Name: |
Arachidonic acid |
CAS: |
506-32-1 |
Synonyms: |
Arachidonate |
IUPAC Name: | (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid |
Description: | Arachidonic acid is an essential fatty acid and a precursor in the biosynthesis of thromboxanes, prostaglandins and leukotrienes. It is a transient, critical substrate for the biosynthesis of eicosanoid second messengers. It is an important cellular signaling mediator in a variety of biological processes, including smooth chemotaxis, muscle contraction, apoptosis, cell proliferation and differentiation. It exits in liver, brain, glandular organs, and depot fats of animals and a constituent of animal phosphatides. It could bind to the subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). It stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules. |
Molecular Weight: | 304.47 |
Molecular Formula: | C20H32O2 |
Canonical SMILES: | CCCCCC=CCC=CCC=CCC=CCCCC(=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- |
InChI Key: | YZXBAPSDXZZRGB-DOFZRALJSA-N |
Boiling Point: | 169-171 °C at 0.1 mmHg |
Melting Point: | -49°C |
Flash Point: | 336.3°C |
Purity: | 98 % |
Density: | 0.922 g/cm3 |
Appearance: | Clear to slight yellow liquid |
Storage: | -20°C |
MDL: | MFCD00004417 |
LogP: | 6.21670 |
Refractive Index: | 1.4872 |
Stability: | Stable under normal temperatures and pressures. |
Vapor Pressure: | 0.00000015 [mmHg] |
GHS Hazard Statement: | H302 (97.06%): Harmful if swallowed [Warning Acute toxicity, oral]; H312 (97.06%): Harmful in contact with skin [Warning Acute toxicity, dermal]; H315 (97.06%): Causes skin irritation [Warning Skin corrosion/irritation]; H319 (97.06%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]; H332 (97.06%): Harmful if inhaled [Warning Acute toxicity, inhalation]; H335 (97.06%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
Precautionary Statement: | P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 |
Signal Word: | Warning |
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PMID | Publication Date | Title | Journal |
33730601 | 20210501 | Etoricoxib may inhibit cytokine storm to treat COVID-19 | Medical hypotheses |
33067036 | 20210101 | Impaired production of the skin barrier lipid acylceramide by CYP4F22 ichthyosis mutations | Journal of dermatological science |
32668280 | 20200901 | The selective lipoprotein-associated phospholipase A2 inhibitor darapladib triggers irreversible actions on glioma cell apoptosis and mitochondrial dysfunction | Toxicology and applied pharmacology |
32220568 | 20200801 | Increased PUFA levels in kidney epithelial cells in the course of diclofenac toxicity | Toxicology in vitro : an international journal published in association with BIBRA |
32387183 | 20200701 | 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) alters hepatic polyunsaturated fatty acid metabolism and eicosanoid biosynthesis in female Sprague-Dawley rats | Toxicology and applied pharmacology |
Complexity: | 362 |
Compound Is Canonicalized: | Yes |
Covalently-Bonded Unit Count: | 1 |
Defined Atom Stereocenter Count: | 0 |
Defined Bond Stereocenter Count: | 4 |
Exact Mass: | 304.240230259 |
Formal Charge: | 0 |
Heavy Atom Count: | 22 |
Hydrogen Bond Acceptor Count: | 2 |
Hydrogen Bond Donor Count: | 1 |
Isotope Atom Count: | 0 |
Monoisotopic Mass: | 304.240230259 |
Rotatable Bond Count: | 14 |
Topological Polar Surface Area: | 37.3 |
Undefined Atom Stereocenter Count: | 0 |
Undefined Bond Stereocenter Count: | 0 |
XLogP3: | 6.3 |
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