Oleoyl glutamic acid

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

MedKoo CAT#: 597123

CAS#: 4627-61-6

Description: Oleoyl glutamic acid is a diacylglycerol analog.


Chemical Structure

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Oleoyl glutamic acid
CAS# 4627-61-6

Theoretical Analysis

MedKoo Cat#: 597123
Name: Oleoyl glutamic acid
CAS#: 4627-61-6
Chemical Formula: C23H41NO5
Exact Mass: 411.2985
Molecular Weight: 411.58
Elemental Analysis: C, 67.12; H, 10.04; N, 3.40; O, 19.44

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Oleoyl glutamic acid; Glutamic acid, N-oleoyl-; NSC-513733; NSC 513733; NSC513733;

IUPAC/Chemical Name: oleoyl-L-glutamic acid

InChi Key: UUFVSGRELDGPGL-QJRAZLAKSA-N

InChi Code: InChI=1S/C23H41NO5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(25)24-20(23(28)29)18-19-22(26)27/h9-10,20H,2-8,11-19H2,1H3,(H,24,25)(H,26,27)(H,28,29)/b10-9-/t20-/m0/s1

SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(CCCCCCC/C=C\CCCCCCCC)=O

Appearance: Solid powder

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: >2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 411.58 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.

Recalculate based on batch purity %
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

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Reconstitution Calculator

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1: Nishizawa K, Nishizawa M, Gnanasambandam R, Sachs F, Sukharev SI, Suchyna TM. Effects of Lys to Glu mutations in GsMTx4 on membrane binding, peptide orientation, and self-association propensity, as analyzed by molecular dynamics simulations. Biochim Biophys Acta. 2015 Nov;1848(11 Pt A):2767-78. doi: 10.1016/j.bbamem.2015.09.003. Epub 2015 Sep 2. PubMed PMID: 26342676; PubMed Central PMCID: PMC4598310.

2: Furuki T, Sakurai M. Group 3 LEA protein model peptides protect liposomes during desiccation. Biochim Biophys Acta. 2014 Nov;1838(11):2757-66. doi: 10.1016/j.bbamem.2014.07.009. Epub 2014 Jul 15. PubMed PMID: 25037007.

3: Sharpe S, Grant CW, Barber KR, Giusti J, Morrow MR. Structural implications of a Val-->Glu mutation in transmembrane peptides from the EGF receptor. Biophys J. 2001 Dec;81(6):3231-9. PubMed PMID: 11720988; PubMed Central PMCID: PMC1301782.

4: Jolly-Tornetta C, Gao ZY, Lee VM, Wolf BA. Regulation of amyloid precursor protein secretion by glutamate receptors in human Ntera 2 neurons. J Biol Chem. 1998 May 29;273(22):14015-21. PubMed PMID: 9593752.

5: Mitrakos P, Macdonald PM. Domains in cationic lipid plus polyelectrolyte bilayer membranes: detection and characterization via 2H nuclear magnetic resonance. Biochemistry. 1997 Nov 4;36(44):13646-56. PubMed PMID: 9354634.

6: Ruehr ML, Zhang L, Dorman RV. Lipid-dependent modulation of Ca2+ availability in isolated mossy fiber nerve endings. Neurochem Res. 1997 Oct;22(10):1215-22. PubMed PMID: 9342725.

7: Zhang L, Ruehr ML, Dorman RV. Arachidonic acid and oleoylacetylglycerol induce a synergistic facilitation of Ca(2+)-dependent glutamate release from hippocampal mossy fiber nerve endings. J Neurochem. 1996 Jan;66(1):177-85. PubMed PMID: 8522951.

8: Coderre TJ, Yashpal K. Intracellular messengers contributing to persistent nociception and hyperalgesia induced by L-glutamate and substance P in the rat formalin pain model. Eur J Neurosci. 1994 Aug 1;6(8):1328-34. PubMed PMID: 7526941.

9: Weiler IJ, Greenough WT. Metabotropic glutamate receptors trigger postsynaptic protein synthesis. Proc Natl Acad Sci U S A. 1993 Aug 1;90(15):7168-71. PubMed PMID: 8102206; PubMed Central PMCID: PMC47097.

10: Zhang L, Dorman RV. Synergistic potentiation of glutamate release by arachidonic acid and oleoyl-acetyl-glycerol. Brain Res Bull. 1993;32(4):437-41. PubMed PMID: 8106127.

11: Casado M, Zafra F, Aragón C, Giménez C. Activation of high-affinity uptake of glutamate by phorbol esters in primary glial cell cultures. J Neurochem. 1991 Oct;57(4):1185-90. PubMed PMID: 1680157.

12: Yamamoto D. Activation of protein kinase C promotes glutamate-mediated transmission at the neuromuscular junction of the mealworm. J Physiol. 1988 Jun;400:691-700. PubMed PMID: 2901491; PubMed Central PMCID: PMC1191831.

13: Lynch MA, Bliss TV. Long-term potentiation of synaptic transmission in the hippocampus of the rat; effect of calmodulin and oleoyl-acetyl-glycerol on release of [3H]glutamate. Neurosci Lett. 1986 Apr 11;65(2):171-6. PubMed PMID: 2872624.