Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

A1221

Sigma-Aldrich

AH6809

≥98%, crystalline solid or supercooled liquid

Synonym(s):

6-Isopropoxy-9-oxoxanthene-2-carboxylic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C17H14O5
CAS Number:
33458-93-4
Molecular Weight:
298.29
MDL number:
MFCD08056083
UNSPSC Code:
12352200
PubChem Substance ID:
329770690
NACRES:
NA.77

Quality Level

100

assay

≥98%

form

crystalline solid or supercooled liquid

solubility

ethanol: soluble 2.5 mg/mL
DMSO or DMF: soluble 8 mg/mL

SMILES string

CC(C)Oc1ccc2c(Oc3ccc(cc3C2=O)C(O)=O)c1

InChI

1S/C17H14O5/c1-9(2)21-11-4-5-12-15(8-11)22-14-6-3-10(17(19)20)7-13(14)16(12)18/h3-9H,1-2H3,(H,19,20)

InChI key

AQFFXPQJLZFABJ-UHFFFAOYSA-N

Application

AH6809 has been used:
  • as a prostaglandin E2 receptor 1 & 2 (EP1/2) antagonist to analyze its effects on cyclooxygenase-2 /prostaglandin E2 (COX-2/PGE2) signaling in the angiogenic feedback of endothelial cells to hypoxia
  • as an EP2 antagonist to study its effects on tumor angiogenesis in human prostate cancer cell lines
  • as an EP2 antagonist to analyze its effects on overexpression of amyloid precursor protein (APP)

Biochem/physiol Actions

AH6809 plays a role in antagonizing the proliferation of non-small cell lung cancer cell lines.
DP/EP prostanoid receptor antagonist; has the highest affinity for DP receptors, but also acts as a weak antagonist at murine EP1 and EP2 prostanoid receptors.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Amy M Pooler et al.
Neuroscience letters, 362(2), 127-130 (2004-06-15)
We investigated the effects of prostaglandin E2 (PGE2) on amyloid precursor protein (APP) expression in cultured rat microglia. PGE2 treatment significantly increased the expression of APP holoprotein and was associated with an elevation in cyclic AMP (cAMP). Direct activation of
Shalini Jain et al.
Cancer research, 68(19), 7750-7759 (2008-10-03)
In cancer management, the cyclooxygenase (COX)-targeted approach has shown great promise in anticancer therapeutics. However, the use of COX-2 inhibitors has side effects and health hazards; thus, targeting its major metabolite prostaglandin E(2) (PGE(2))-mediated signaling pathway might be a rational
Sarah A Maher et al.
American journal of respiratory and critical care medicine, 180(10), 923-928 (2009-09-05)
A significant population of patients with severe asthma and chronic obstructive pulmonary disease is less responsive to beta(2)-adrenoceptor agonists and corticosteroids, and there are possible safety issues concerning long-term use of these drugs. Inhaled prostaglandin E(2) (PGE(2)) is antiinflammatory and
Hiroyuki Isshiki et al.
Biochemical and biophysical research communications, 489(3), 305-311 (2017-06-01)
Methods for the artificial three-dimensional (3D) culture of mouse and human small-intestinal and large-intestinal stem cells have been established with CD24 Using various tissue homogenates, we investigated the colonic organoid forming capacity under the TMDU protocol immediately adjacent to Ootani's
Marchessini Casibang et al.
Lung cancer (Amsterdam, Netherlands), 36(1), 33-42 (2002-03-14)
The effects of prostaglandin (PG)E2 on lung cancer cells were investigated. 3H-PGE2 bound with high affinity to membranes derived from small cell lung cancer (SCLC) and non-SCLC (NSCLC) cell lines. Using NSCLC NCI-H1299 membranes, specific 3H-PGE2 binding to NCI-H1299 membranes
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service