The primary PGD2 metabolite
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11β-Prostaglandin F2α

Item No. 16520

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z,9α,11β,13E,15S)-9,11,15-trihydroxy-prosta-5,13-dien-1-oic acid
CAS Number
38432-87-0
Synonyms
  • 9α,11β-PGF2α
  • 11β-PGF2α
  • 11-epi PGF2α
Molecular Formula
C20H34O5
Formula Weight
354.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 100 mg/mlEthanol: 100 mg/mlPBS pH 7.2: 10 mg/ml
SMILES
O[C@@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@@H](C/C=C\CCCC(O)=O)[C@@H](O)C1
InChi Code
InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19-/m0/s1
InChi Key
PXGPLTODNUVGFL-ZWAKLXPCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $154

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    5 mg

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    10 mg

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    Product Description

    11β-Prostaglandin F2α (11β-PGF2α) is the primary metabolite of PGD2 (Item No. 12010).1 It is formed from PGD2 via the NADPH-dependent aldo-keto reductase PGF synthase (PGFS; Item No. 10007940) in the liver or lung.2 11β-PGF2α induces contraction of isolated cat iris sphincter, which endogenously expresses high levels of PGF2α (FP) receptors, with an EC50 value of 0.045 µM.1 It also induces contraction of isolated human bronchial smooth muscle when used at concentrations ranging from 0.1 to 30 µM.3 11β-PGF2α (0.1 and 1 µM) induces phosphorylation of ERK and CREB, as well as increases the viability of MCF-7 breast cancer cells stably expressing the FP receptor when used at concentrations of 0.1 and 1 µM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Giles, H., Bolofo, M.L., Lydford, S.J., et al. A comparative study of the prostanoid receptor profile of 9α 11 β-prostaglandin F2 and prostaglandin D2. Br. J. Pharmacol. 104(2), 541-549 (1991).

    2. Watanabe, K. Prostaglandin F synthase. Prostaglandins Other Lipid Mediat. 68-69, 401-407 (2002).

    3. Coleman, R.A., and Sheldrick, R.L.G. Prostanoid-induced contraction of human bronchial smooth muscle is mediated by TP-receptors. Br. J. Pharmacol. 96(3), 688-692 (1989).

    4. Yoda, T., Kikuchi, K., Miki, Y., et al. 11β-Prostaglandin F2α, a bioactive metabolite catalyzed by AKR1C3, stimulates prostaglandin F receptor and induces slug expression in breast cancer. Mol. Cell. Endocrinol. 413, 236-247 (2015).

    Product Citations

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).