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D8174

Sigma-Aldrich

9,11-Dideoxy-11α,9α-epoxymethanoprostaglandin F2α

solution, 10 mg/mL in methyl acetate

Synonym(s):

U-46619, U46619

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About This Item

Empirical Formula (Hill Notation):
C21H34O4
CAS Number:
56985-40-1
Molecular Weight:
350.49
Beilstein/REAXYS Number:
4267334
MDL number:
MFCD00135238
UNSPSC Code:
12352211
PubChem Substance ID:
24894197
NACRES:
NA.77

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

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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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Central nervous system

supp_hazards

EUH066

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

14.0 °F

flash_point_c

-10 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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