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Merck

D8174

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

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

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
NACRES:
NA.77
PubChem Substance ID:
24894197
UNSPSC Code:
12352211
MDL number:
MFCD00135238
Beilstein/REAXYS Number:
4267334

Key Documents

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Product Name

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

Related Categories

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

WGK 2

flash_point_f

14.0 °F

flash_point_c

-10 °C

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Group 4: Flammable liquids + Type 1 petroleums + Hazardous rank II + Water insoluble liquid

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

D8174-5MG:4548173911526 + D8174-1MG-PW: + D8174-5MG-PW: + D8174-1MG:4548173911519 + D8174-10MG:4548173911502 + D8174-10MG-PW: + D8174-VAR: + D8174-5MG-LBL: + D8174-BULK:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
0000341596
0000284213
0000284233
0000284233
0000341596

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Journal of vascular research, 47(5), 384-398 (2010-01-30)
We investigated the potential role of Raf-1 kinase in mesenteric arterial contraction. Inhibitors of Raf-1 kinase, GW5074, L779450 and ZM 336372 reversed phenylephrine (PE)-induced mesenteric vascular contraction. Studies in vivo in rats showed that GW5074 inhibited PE-induced increase in mean
Jill Overend et al.
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We have investigated the neurogenic factors inducing relaxation in the intraocular segment of the bovine long posterior ciliary artery. In precontracted vessels, electrical field stimulation (EFS, 0.5-128 Hz, 10 s trains) in the presence of guanethidine (30 microM) evoked biphasic
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