(15R)-PGE2 | CAS# 38873-82-4 | eicosanoid

MedKoo Cat#: 412679 | Name: (15R)-PGE2

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

15(R)-Prostaglandin E2 is the C-15 epimer of the naturally occurring 15(S)-PGE2 (sc-201225) isomer; the most physiologically abundant eicosanoid, which is produced predominantly from arachidonic acid (sc-200770) by COX and PGES, and exists at some level in nearly all cell types. PGE2 acts on four different receptors termed EP1 through EP4 yielding an astounding array of biological effects, but this compound shows much lower potency in most biological assays; however acid catalyzed epimerization can convert this compound to the active form - 15(S)-Prostaglandin E2.

Chemical Structure

(15R)-PGE2

CAS#38873-82-4

Theoretical Analysis

MedKoo Cat#: 412679

Name: (15R)-PGE2

CAS#: 38873-82-4

Chemical Formula: C20H32O5

Exact Mass: 352.2250

Molecular Weight: 352.47

Elemental Analysis: C, 68.15; H, 9.15; O, 22.70

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 285.00	2 Weeks
5mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

(15R)-PGE2; 15(R)-Prostaglandin E2

IUPAC/Chemical Name

(Z)-7-((1R,2R,3R)-3-hydroxy-2-((R,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid

InChi Key

XEYBRNLFEZDVAW-GKEZHNTDSA-N

InChi Code

InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17-,19-/m1/s1

SMILES Code

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

Appearance

A solution in methyl acetate

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 352.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Reina E, Ramos FA, Castellanos L, Aragón M, Ospina LF. Anti-inflammatory R-prostaglandins from Caribbean Colombian soft coral Plexaura homomalla. J Pharm Pharmacol. 2013 Nov;65(11):1643-52. doi: 10.1111/jphp.12138. PMID: 24118067. 2: Valmsen K, Järving I, Boeglin WE, Varvas K, Koljak R, Pehk T, Brash AR, Samel N. The origin of 15R-prostaglandins in the Caribbean coral Plexaura homomalla: molecular cloning and expression of a novel cyclooxygenase. Proc Natl Acad Sci U S A. 2001 Jul 3;98(14):7700-5. doi: 10.1073/pnas.131022398. Epub 2001 Jun 26. PMID: 11427702; PMCID: PMC35405. 3: Camras CB, Alm A. Initial clinical studies with prostaglandins and their analogues. Surv Ophthalmol. 1997 Feb;41 Suppl 2:S61-8. doi: 10.1016/s0039-6257(97)80009-4. PMID: 9154278. 4: Xu RM, Zhang SR, Jin BY, Han C, Wu YL. [Antisecretory effect of dl-(15R)-15 methyl-PGE2 methyl ester (PG6E) on perfusing rats in vivo]. Yao Xue Xue Bao. 1997;32(1):79-80. Chinese. PMID: 11243226. 5: Pullen RH, Cox JW. Determination of (15R)- and (15S)-15-methylprostaglandin E2 in human plasma with picogram per milliliter sensitivity by column-switching high-performance liquid chromatography. J Chromatogr. 1985 Oct 11;343(2):271-83. doi: 10.1016/s0378-4347(00)84597-1. PMID: 4066871. 6: Schneider C, Manier ML, Hachey DL, Brash AR. Detection of the 15-acetate of prostaglandin E2 methyl ester as a prominent component of the prostaglandins in the gorgonian coral Plexaura homomalla. Lipids. 2002 Feb;37(2):217-21. doi: 10.1007/s11745-002-0883-5. PMID: 11908914. 7: Fujiwara S, Shimamoto C, Nakanishi Y, Katsu K, Kato M, Nakahari T. Enhancement of Ca2+-regulated exocytosis by indomethacin in guinea-pig antral mucous cells: arachidonic acid accumulation. Exp Physiol. 2006 Jan;91(1):249-59. doi: 10.1113/expphysiol.2005.032482. Epub 2005 Nov 1. PMID: 16263797. 8: Imanishi M, Kawamura M, Akabane S, Matsushima Y, Kuramochi M, Ito K, Ohta M, Kimura K, Takamiya M, Omae T. Aspirin lowers blood pressure in patients with renovascular hypertension. Hypertension. 1989 Nov;14(5):461-8. doi: 10.1161/01.hyp.14.5.461. PMID: 2680959. 9: Zhang SR, Xu RM, Jin BY, Wu YL, Han C. [Protection of dl-(15R)-15 methyl-PGE2 methyl ester (PG6E) on experimental ulcers in rats]. Yao Xue Xue Bao. 1996;31(10):746-50. Chinese. PMID: 9863242. 10: Cox JW, Bothwell WM, Pullen RH, Wynalda MA, Fitzpatrick FA, VanderLugt JT. Plasma levels of the prodrug, arbaprostil, [(15R)-15-methylprostaglandin E2], and its active, antiulcer (15S) epimer in humans after single dose oral administration. J Pharm Sci. 1986 Nov;75(11):1107-12. doi: 10.1002/jps.2600751118. PMID: 3820107.