Name: QUISQUALIC ACID
SKU: 52809-07-1

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Basic Information

Molecular Structure:
CAS No.:	52809-07-1
Name:	QUISQUALIC ACID
Article Data:	8

Formula:	C₅H₇N₃O₅
Molecular Weight:	189.128
Synonyms:	1,2,4-Oxadiazolidine-2-propanoicacid, a-amino-3,5-dioxo-, (S)-;Quisqualic acid (7CI);L-Quisqualic acid;Quisqualinic acid;S-Quisqualic acid;
Density:	1.679 g/cm³
Melting Point:	185-187 °C
Boiling Point:	324.36°C (rough estimate)
Solubility:	NH₄OH 1 M: 20 mg/mL, clear, colorless
Appearance:	off-white solid
Hazard Symbols:	Xn
Risk Codes:	20/21/22
Safety:	26-36
PSA:	131.32000
LogP:	-1.75820

Synthetic route

: 5147-00-2
O-acetyl-L-serine

: 24603-68-7
[1,2,4]oxadiazolidine-3,5-dione

: 52809-07-1
quisqualic acid

Conditions

Conditions	Yield
With gallium(III) nitrate; pyridoxal 5'-phosphate In water at 62 - 65℃; for 2h; pH=5.0;	10%
cysteine synthases from Pisum sativum
With acetate buffer; metal ions; pyridoxal 5'-phosphate
isoenzyme B (cysteine synthase fromm Quisqualis indica var. villosa)

: Sodium; (S)-2-tert-butoxycarbonylamino-3-(3,5-dioxo-[1,2,4]oxadiazolidin-2-yl)-propionate

: 52809-07-1
quisqualic acid

Conditions

Conditions	Yield
With Dowex 50W-X8(H); trifluoroacetic acid 1.) 20 deg C, 1 h; Yield given;

: 56-45-1
L-serin

: 24603-68-7
[1,2,4]oxadiazolidine-3,5-dione

: 52809-07-1
quisqualic acid

Conditions

Conditions	Yield
With acetate buffer; metal ions; pyridoxal 5'-phosphate

: 52-90-4
L-Cysteine

: 24603-68-7
[1,2,4]oxadiazolidine-3,5-dione

: 52809-07-1
quisqualic acid

Conditions

Conditions	Yield
With Tris-HCl buffer at 30℃; for 0.166667h; β-cyano-L-alanine synthase (from Spinacia oleracea, Chenopodiaceae);

: (S)-2-tert-Butoxycarbonylamino-3-(3,5-dioxo-[1,2,4]oxadiazolidin-2-yl)-propionic acid tert-butyl ester

: 52809-07-1
quisqualic acid

Conditions

Conditions	Yield
With Amberlite IR-45; methoxybenzene; trifluoroacetic acid In N,N-dimethyl-formamide at 0℃; for 16h; Yield given;

: 97839-01-5
((S)-2-Ethoxycarbonylaminocarbonyl-5-oxo-isoxazolidin-4-yl)-carbamic acid tert-butyl ester

: 52809-07-1
quisqualic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / tetrahydrofuran; H2O / 0.33 h / 20 °C 2: 1.) CF3COOH, 2.) Dowex 50W-X8(H) / 1.) 20 deg C, 1 h View Scheme

: 52809-07-1
quisqualic acid

: 1483-07-4
L-2-Amino-3-ureido-propanoic acid

Conditions

Conditions	Yield
With hydrogen; platinum(IV) oxide In water at 20℃; for 3h;

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Specification

The IUPAC name of L-Quisqualic acid is (2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid. With the CAS registry number 52809-07-1, it is also named as Quisqualic acid. The product's categories are amino acids 13C, 2H, 15N, amino acids & derivatives, neurochemicals, glutamate receptor, glutamate. In addition, its molecular formula is C₅H₇N₃O₅ and its molecular weight is 189.13. It is off-white solid, which should be cool and dry place at 2-8 °C. Besides, you must keep container tightly sealed. And you should ensure that workplaces have good ventilation or exhaust. Furthermore, the product is stable and incompatible with strong oxidizing agents, which is souble in NH₄OH.

The other characteristics of L-Quisqualic acid can be summarized as: (1)ACD/LogP: -1.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.36; (4)ACD/LogD (pH 7.4): -4.38; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)H bond acceptors: 8; (10)H bond donors: 4; (11)Freely Rotating Bonds: 4; (12)XLogP3-AA: -3.9; (13)Rotatable Bond Count: 3; (14)Tautomer Count: 3; (15)Exact Mass: 189.03857; (16)MonoIsotopic Mass: 189.03857; (17)Topological Polar Surface Area: 122; (18)Heavy Atom Count: 13; (19)Complexity: 265; (20)Index of Refraction: 1.571; (21)Molar Refractivity: 37.02 cm³; (22)Molar Volume: 112.6 cm³; (23)Polarizability: 14.67×10^-24cm³; (24)Surface Tension: 79 dyne/cm; (25)Density: 1.679 g/cm³; (26)Melting Point: 185-187 °C.

Uses of L-Quisqualic acid: this chemical is An amino acid that is able to function as an agonist at multiple excitatory amino acid receptor substrates in the central nervous system. It also has high affinity for the kainate, AMPA and the metabotropic receptors. Additionally, it Inhibits the Ca²⁺ and Cl^- depending.

When you are using this chemical, please be cautious about it as the following: it is harmful by inhalation, in contact with skin and if swallowed. Please wear suitable protective clothing. Moreover, in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
(1)SMILES:O=C1NC(=O)ON1C[C@H](N)C(=O)O
(2)InChI:InChI=1/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
(3)InChIKey:ASNFTDCKZKHJSW-REOHCLBHBE
(4)Std. InChI:InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
(5)Std. InChIKey:ASNFTDCKZKHJSW-REOHCLBHSA-N