N-Phthaloylglutamic acid

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

MedKoo CAT#: 597149

CAS#: 3227-01-8

Description: N-Phthaloylglutamic acid is a hydrolytic metabolite of thalidomide.

Chemical Structure

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N-Phthaloylglutamic acid
CAS# 3227-01-8
Instruction

Theoretical Analysis

MedKoo Cat#: 597149
Name: N-Phthaloylglutamic acid
CAS#: 3227-01-8
Chemical Formula: C13H13NO7
Exact Mass: 295.07
Molecular Weight: 295.240
Elemental Analysis: C, 52.89; H, 4.44; N, 4.74; O, 37.93

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.

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Synonym: N-Phthaloylglutamic acid; alpha-N-Phthaloylglutamic acid; PhGA; N,N-Phthaloyl-L-glutamic acid;

IUPAC/Chemical Name: (2-carboxybenzoyl)-L-glutamic acid

InChi Key: QIWKCQDJZPRXNS-VIFPVBQESA-N

InChi Code: InChI=1S/C13H13NO7/c15-10(16)6-5-9(13(20)21)14-11(17)7-3-1-2-4-8(7)12(18)19/h1-4,9H,5-6H2,(H,14,17)(H,15,16)(H,18,19)(H,20,21)/t9-/m0/s1

SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=CC=C1C(O)=O)=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: >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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 295.24 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Ramagiri S, Gupte R, Rakov I, Yates CR, Miller DD. Quantitative chiral analysis of phthaloylglutamic acid and related analogs by a single ratio kinetic method using electrospray ionization and matrix-assisted laser desorption techniques. Rapid Commun Mass Spectrom. 2008;22(5):639-46. doi: 10.1002/rcm.3405. PubMed PMID: 18247407.

2: Attila C, Ueda A, Wood TK. PA2663 (PpyR) increases biofilm formation in Pseudomonas aeruginosa PAO1 through the psl operon and stimulates virulence and quorum-sensing phenotypes. Appl Microbiol Biotechnol. 2008 Feb;78(2):293-307. Epub 2007 Dec 22. PubMed PMID: 18157527.

3: Kenyon BM, Browne F, D'Amato RJ. Effects of thalidomide and related metabolites in a mouse corneal model of neovascularization. Exp Eye Res. 1997 Jun;64(6):971-8. PubMed PMID: 9301478.

4: North WG, Fay MJ, Du J, Cleary M, Gallagher JD, McCann FV. Presence of functional NMDA receptors in a human neuroblastoma cell line. Mol Chem Neuropathol. 1997 Jan-Feb;30(1-2):77-94. PubMed PMID: 9138430.

5: Koreshonkov ON, Perestenko PV, Dumpis MA, Piotrovskiĭ LB. [Effects of N-phthalamoyl-L-glutaminic acid, a selective agonist of NMDA receptor, on binding of 3H-L-glutamate with synaptic membranes of the hippocampus]. Biull Eksp Biol Med. 1992 Jun;113(6):563-5. Russian. PubMed PMID: 1446016.

6: Kocher-Becker U, Kocher W, Ockenfels H. [Embryotoxic interactions between a hydrolysis product of thalidomide and the surfactant Tween 20 in mice]. Z Naturforsch C. 1992 Jan-Feb;47(1-2):155-69. German. PubMed PMID: 1610476.

7: Kiskin NI, Tsyndrenko AYa, Dumpis MA, Piotrovsky LB, Krishtal OA. A novel selective NMDA agonist, N-phthalamoyl-L-glutamic acid (PhGA). Neuroreport. 1991 Jan;2(1):29-32. PubMed PMID: 1685102.

8: Kocher-Becker U, Kocher W, Ockenfels H. Teratogenic activity of a hydrolytic thalidomide metabolite in mice. Naturwissenschaften. 1982 Apr;69(4):191-2. PubMed PMID: 7088198.

9: Gagliardi V. [Teratogenic effects induced by N-phthaloylglutamic acid imide in the maxillofacial region]. Riv Ital Stomatol. 1971 Apr;26(4):241-70. Italian. PubMed PMID: 5003550.