An internal standard for the quantification of PGE2-1-glyceryl ester
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Unlabeled Version(s)
10140Prostaglandin E2-1-glyceryl ester
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Prostaglandin E2-1-glyceryl ester-d5

Item No. 10004197

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-oxo-11α,15S-dihydroxy-prosta-5Z,13E-dien-1-oic acid,1-glyceryl ester-d5
Synonyms
  • PGE2-1-glyceryl ester-d5
Molecular Formula
C23H33D5O7
Formula Weight
431.6
Purity
≥99% deuterated forms (d1-d5)
Formulation
A 500 µg/ml solution in acetonitrile
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 100 µg/ml
SMILES
O=C1[C@H](C/C=C\CCCC(OC([2H])([2H])C(O)([2H])C([2H])([2H])O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C1
InChi Code
InChI=1S/C23H38O7/c1-2-3-6-9-17(25)12-13-20-19(21(27)14-22(20)28)10-7-4-5-8-11-23(29)30-16-18(26)15-24/h4,7,12-13,17-20,22,24-26,28H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,18?,19+,20+,22+/m0/s1/i15D2,16D2,18D
InChi Key
RJXVYMMSQBYEHN-OIDPAJOKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 µg

    $107

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    100 µg

    $203

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    500 µg

    $845

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    Product Description

    Prostaglandin E2-1-glyceryl ester-d5 (PGE2-1-glyceryl ester-d5) is intended for use as an internal standard for the quantification of PGE2-1-glyceryl ester by GC- or LC-MS. 2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the central cannabinoid receptor.1,2 Incubation of 2-AG with cyclooxygenase-2 and specific PGH2 isomerases in cell cultures and isolated enzyme preparations results in PG glycerol ester formation.3 The biosynthesis of PGH, PGD, PGE, PGF, and thromboxane A-2-glyceryl ester compounds have all been documented. The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 2:1-glyceryl ester mixture in typical aqueous media. While the stability and metabolism of these prostaglandin products has been investigated, little is known about their intrinsic biological activity.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem. Biophys. Res. Commun. 229(1), 58-64 (1996).

    2. Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J. Biochem. 122(4), 890-895 (1997).

    3. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. The Journal of Biological Chemisty 277(47), 44877-44885 (2002).

    4. Kozak, K.R., Crews, B.C., Ray, J.L., et al. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. The Journal of Biological Chemisty 276(40), 36993-36998 (2001).