D8174

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

Name: 9,11-Dideoxy-11α,9α-epoxymethanoprostaglandin F<SUB>2α</SUB>
Brand: SIGMA

≥98% (HPLC), solution, thromboxane A2 agonist

Synonym(s):

U-46619, U46619

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All Photos(1)

About This Item

Empirical Formula (Hill Notation):

C₂₁H₃₄O₄

CAS Number:

56985-40-1

Molecular Weight:

350.49

NACRES:

NA.77

PubChem Substance ID:

24894197

UNSPSC Code:

12352211

MDL number:

MFCD00135238

Beilstein/REAXYS Number:

4267334

Product Name

9,11-Dideoxy-11α,9α-epoxymethanoprostaglandin F_2α, solution, 10 mg/mL in methyl acetate

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

SMILES string

CCCCC[C@H](O)\C=C\[C@H]1C2CC(CO2)[C@@H]1C\C=C/CCCC(O)=O

InChI key

LQANGKSBLPMBTJ-REGKDVDGSA-N

form

solution

concentration

10 mg/mL in methyl acetate

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

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Related Categories

Bioactive Small Molecules

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.

General description

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

pictograms

GHS02,GHS07

signalword

Danger

hcodes

H225,H319,H336

pcodes

P210 - P305 + P351 + P338

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

WGK 2

flash_point_f

14.0 °F

flash_point_c

-10 °C

ppe

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

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