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D0160

Sigma-Aldrich

16,16-Dimethylprostaglandin E2

methyl acetate solution

Synonym(s):

16,16-Dimethyl-PGE2

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About This Item

Empirical Formula (Hill Notation):
C22H36O5
CAS Number:
39746-25-3
Molecular Weight:
380.52
MDL number:
MFCD00151141
UNSPSC Code:
12352211
PubChem Substance ID:
24893214
NACRES:
NA.25

biological source

synthetic (organic)

Assay

≥98% (HPLC)

form

methyl acetate solution

concentration

10 mg/mL

functional group

carboxylic acid

lipid type

unsaturated FAs

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C22H36O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h6,8,12-13,16-17,19-20,24-25H,4-5,7,9-11,14-15H2,1-3H3,(H,26,27)/b8-6-,13-12+/t16-,17-,19-,20-/m1/s1

InChI key

QAOBBBBDJSWHMU-WMBBNPMCSA-N

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Preparation Note

Agitation or brief ultrasonication may be necessary for restoration of solutions which have been precipitated due to freezing. The methyl acetate can be removed using N2 or vacuum. Stock solutions of 1-5 mg/ml in absolute alcohol may be prepared and diluted with isotonic saline.

Pictograms

FlameExclamation mark
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)

8.6 °F

Flash Point(C)

-13 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Sara S Roscioni et al.
British journal of pharmacology, 162(1), 193-209 (2010-09-02)
Changes in airway smooth muscle (ASM) phenotype may contribute to the pathogenesis of airway disease. Platelet-derived growth factor (PDGF) switches ASM from a contractile to a proliferative, hypo-contractile phenotype, a process requiring activation of extracellular signal-regulated kinase (ERK) and p70(S6)
Tomonori Kunikata et al.
Digestive diseases and sciences, 47(4), 894-904 (2002-05-07)
We evaluated the effect of various PGE analogs specific to EP receptor subtypes on indomethacin-induced small intestinal lesions in rats and investigated the relationship of EP receptor subtype with the PGE action using EP receptor knockout mice. Animals were administered
Elena Piazuelo et al.
Prostaglandins & other lipid mediators, 81(3-4), 150-161 (2006-11-07)
Accumulating evidence suggests that COX-2-derived prostaglandin E(2) (PGE(2)) plays an important role in esophageal adenocarcinogenesis. Recently, PGE(2) receptors (EP) have been shown to be involved in colon cancer development. Since it is not known which receptors regulate PGE(2) signals in
Genhai Zhu et al.
Gynecologic oncology, 94(2), 422-426 (2004-08-07)
Emerging evidence supports a role for prostaglandins (PG) and their synthesizing enzyme, cyclooxygenase (COX), in tumor angiogenesis. The objective of this study was to investigate the effects of prostaglandin E(2) (PGE(2)) on the expression of vascular endothelial growth factor (VEGF)
Brigitta M Peskar et al.
The Journal of pharmacology and experimental therapeutics, 301(3), 969-974 (2002-05-23)
This study compares the involvement of ATP-sensitive potassium (K(ATP)) channels and prostaglandins in various forms of gastroprotection in the rat. Instillation of 1 ml of 70% ethanol induced severe gastric mucosal damage (lesion index 39 +/- 0.8), which was substantially
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