D8174

9,11-Dideoxy-11α,9α-epoxymethanoprostaglandin F_2α

solution, 10 mg/mL in methyl acetate

• Synonym(s): U-46619, U46619
• Empirical Formula (Hill Notation): C₂₁H₃₄O₄
• CAS Number: 56985-40-1
• Molecular Weight: 350.49
• Beilstein: 4267334
• MDL number: MFCD00135238
• UNSPSC Code: 12352211
• PubChem Substance ID: 24894197
• NACRES: NA.77

Properties

• form: solution
• Quality Level: 200
• concentration: 10 mg/mL in methyl acetate
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: CCCCC[C@H](O)\C=C\[C@H]1C2CC(CO2)[C@@H]1C\C=C/CCCC(O)=O
• InChI: 1S/C21H34O4/c1-2-3-6-9-17(22)12-13-19-18(16-14-20(19)25-15-16)10-7-4-5-8-11-21(23)24/h4,7,12-13,16-20,22H,2-3,5-6,8-11,14-15H2,1H3,(H,23,24)/b7-4-,13-12+/t16?,17-,18-,19+,20?/m0/s1
• InChI key: LQANGKSBLPMBTJ-REGKDVDGSA-N

Description

General description

9,11-Dideoxy-11α,9α-epoxymethanoprostaglandin F2α is an endoperoxide/thromboxane analog.

Application

9,11-Dideoxy-11α,9α-epoxymethanoprostaglandin F2α has been used:

• to induce aortic smooth muscle (SM) contraction in mice deficient in myosin light chain 9 (Myl9) gene
• to induce contraction as part of vascular reactivity experiments using mice aorta
• as a thromboxane/prostaglandin agonist to study the effect of dithiothreitol (DTT) on mice arterial vessel viability

Biochem/physiol Actions

9,11-Dideoxy-11α,9α-epoxymethanoprostaglandin F2α is a thromboxane A2 agonist. It is useful in in vitro experiments to induce shape change, aggregation, secretion, phosphoinositide hydrolysis, and protein phosphorylation in platelets. It also causes an elevation in the cytosolic Ca⁺⁺ levels slightly affecting the cyclic adenosine monophosphate (cAMP) formation. It acts as a potent stimulator of vascular cell adhesion molecule-1 (VCAM-1), which mediates leukocyte adhesion to the endothelium.

Features and Benefits

This compound is featured on the Prostanoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Danger
• Hazard Statements: H225 - H319 - H336
• Precautionary Statements: P210 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
• Target Organs: Central nervous system
• Supplementary Hazards: EUH066
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 2
• Flash Point(F): 14.0 °F
• Flash Point(C): -10 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves