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QUISQUALIC ACID structure
QUISQUALIC ACID structure

QUISQUALIC ACID

Iupac Name:(2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
CAS No.: 52809-07-1
Molecular Weight:189.127
Modify Date.: 2022-11-22 20:22
Introduction: 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. Inhibits the Ca2+/Cl-dependent glutamic acid uptake system in brain synaptic plasma membrane preparations. View more+
1. Names and Identifiers
1.1 Name
QUISQUALIC ACID
1.2 Synonyms

(+)-QUISQUALIC ACID (2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid (2S)-2-Amino-3-(3-hydroxy-5-oxo-2,5-dihydro-1,2,4-oxadiazol-2-yl)propanoic acid (2S)-2-Amino-3-(5-hydroxy-3-oxo-2,3-dihydro-1,2,4-oxadiazol-2-yl)propanoic acid (L)-(+)-ALPHA-AMINO-3,5-DIOXO-1,2,4-OXADIAZOLIDINE-2-PROPANOIC ACID (αS)-α-Amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoic acid 1,2,4-Oxadiazolidine-2-propanoic acid, α-amino-3,5-dioxo-, (S)- 1,2,4-Oxadiazolidine-2-propanoic acid, α-amino-3,5-dioxo-, (αS)- 3-(3,5-DIOXO-1,2,4-OXADIAZOLIDIN-2-YL)-L-ALANINE beta-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine BETA-(3,5-DIOXO-1,2,4-OXADIZOLIDIN-2-YL)-L-ALANINE BETA-[3,5-DIOXO-1,2,4-OXADIAZOLIDIN-2-YL]-L-ALANINE L-(+)-A-AMINO-3,5-DIOXO-1,2,4-OXADIAZOLIDINE-2-PROPANOIC ACID L(+)-QUISQUALIC ACID L-QUISQUALIC ACID Quisqualinic acid S-Quisqualic acid

1.3 CAS No.
52809-07-1
1.4 CID
40539
1.5 Molecular Formula
C5H7N3O5 (isomer)
1.6 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
1.7 InChIkey
ASNFTDCKZKHJSW-REOHCLBHSA-N
1.8 Canonical Smiles
C(C(C(=O)O)N)N1C(=O)NC(=O)O1
1.9 Isomers Smiles
C([C@@H](C(=O)O)N)N1C(=O)NC(=O)O1
2. Properties
2.1 Density
1.679
2.1 Melting point
185-187°C dec.
2.1 Boiling point
°Cat760mmHg
2.1 Refractive index
1.571
2.1 Flash Point
°C
2.1 Precise Quality
189.03900
2.1 PSA
131.32000
2.1 logP
-1.75820
2.1 Solubility
NH4OH 1 M: 20?mg/mL, clear, colorless
2.2 Appearance
white to off-white
2.3 Storage
Keep Cold.
2.4 Chemical Properties
Off-White Solid
2.5 Color/Form
white to off-white
2.6 pKa
2.12±0.10(Predicted)
2.7 Water Solubility
soluble in ethanol, water. Insoluble in organic solvents.NH4OH 1 M: 20?mg/mL, clear, colorless
2.8 Stability
Stable. Incompatible with strong oxidizing agents.
2.9 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 68 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302+H312+H332 (66.18%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501
3.2 Purification Methods
It has been purified by ion-exchange chromatography on Dowex 50W (x 8, H+ form); the desired fractions are lyophilised and recrystallised from H2O/EtOH. It has IR (KBr) : 3400-2750br, 1830s, 1775s, 1745s and 1605s cm-1;maxand 1H NMR (NaOD/D2O, pH 13) : 3.55-3.57 (1H m, X of ABX, H-2), 3.72-3.85 (2H, AB of ABX, H-3), 1 3C NMR (D2O) : 50.1t, 53.4d, 154.8s, 159.7s and 171.3s. [Baldwin et al. J Chem Soc, Chem Commun 256 1985.] It is a quasiqualate receptor agonist [Joels et al. Proc Natl Acad Sci USA 86 3404 1989]. QUISQUALIC ACIDSupplier
3.3 Usage
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. Inhibits the Ca2+/Cl-dependent glutamic acid uptake system in brain synaptic plasma membrane preparations.
4. Safety and Handling
4.1 Hazard Codes
Xn
4.1 Risk Statements
R20/21/22
4.1 Safety Statements
26-36
4.1 Hazard Declaration
H302-H312-H332
4.1 RIDADR
NONH for all modes of transport
4.1 Caution Statement
P280
4.1 WGK Germany
3
4.1 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

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Acute toxicity - Inhalation, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302+H312+H332 Harmful if swallowed, in contact with skin or if inhaled

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Precursor and Product
8. Other Information
8.0 Usage
Quisqualic acid is used to differentiate between mGluR-1 and mGluR-4. L-Quisqualic acid is an activator of GluR.
8.1 Mesh
Drugs that bind to and activate excitatory amino acid receptors. (See all compounds classified as Excitatory Amino Acid Agonists.)
8.2 Mesh Entry Terms
Quisqualate
9. Computational chemical data
  • Molecular Weight: 189.127g/mol
  • Molecular Formula: C5H7N3O5
  • Compound Is Canonicalized: True
  • XLogP3-AA: -3.9
  • Exact Mass: 189.03857033
  • Monoisotopic Mass: 189.03857033
  • Complexity: 265
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 6
  • Topological Polar Surface Area: 122
  • Heavy Atom Count: 13
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcYBjOAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAAAAAAAHgAUCAAACCjBgAQBCALQAgAIAACQGAAAAAAAAAAgAIGIAAGCQAgAAAAUQAAKFyIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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11. Realated Product Infomation