(S)-(+)-Nipecotic acid

Product Name(S)-(+)-Nipecotic acid
CAS59045-82-8
MFC6H11NO2
MW129.16
EINECS628-683-6
MOL File59045-82-8.mol

Chemical Properties

Melting point	254 °C (dec.)
Boiling point	265.8±33.0 °C(Predicted)
Density	1.125±0.06 g/cm3(Predicted)
refractive index	4.5 ° (C=5, H2O)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Water Solubility	almost transparency in Water
form	Powder
pka	3.88±0.20(Predicted)
color	White
optical activity	[α]/D 3.0 to 6.5°, c = 1 in H2O
InChI	1S/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1
InChIKey	XJLSEXAGTJCILF-YFKPBYRVSA-N
SMILES	OC(=O)[C@H]1CCCNC1
CAS DataBase Reference	59045-82-8(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-22
Safety Statements	26-36
WGK Germany	3
HS Code	29339900
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

White solid

Uses

(+)-Nipecotic acid ((+)-β-Homoproline) is a GABA transport inhibitor with potential antidepressant and anxiolytic activities. (+)-Nipecotic acid can increase the concentration of GABA in the synaptic cleft, thereby enhancing inhibitory neurotransmission. The research on (+)-Nipecotic acid provides a possible direction for the development of new inhibitory compounds for psychiatric diseases[1].

Definition

ChEBI: (S)-nipecotic acid is the (S)-enantiomer of nipecotic acid. It is an enantiomer of a (R)-nipecotic acid.

General Description

(S)-(-)-3-Piperidinecarboxylic acid is an inhibitor of GABA (γ-aminobutyric acid) uptake.

Synthesis

4138-26-5

88495-55-0

498-95-3

(S)-piperidine-3-carboxamide and 3-piperidinecarboxylic acid were synthesized from 3-piperidinecarboxamide by the following steps: Example 3: R-enantioselective hydrolysis of racemic 3-piperidinecarboxamide in Cupriavidus sp. strain KNK-J915 (FERM BP-10739) 1. Prepare a bacterial cell suspension by culturing strain KNK-J915 as in Example 1. 2. 0.1 ml of bacterial cell suspension was mixed with 100 mM phosphate buffer (0.1 ml, pH 7.0) containing 1.0-5.0% racemic 3-piperidine carboxamide. 3. The reaction was carried out by shaking the mixture at 30°C for 35 hours. 4. After completion of the reaction, solids such as bacterial cells were removed by centrifugation. 5. The substrate and products in the reaction mixture were derivatized by reaction with benzyl chlorocarbonate. 6. The resulting derivatives were analyzed by high performance liquid chromatography (HPLC) to determine the conversion (%) and optical purity (ee%). The results were recorded in Table 3. HPLC analysis conditions: - Conversion rate analysis: - Chromatographic column: YMC-A303 (4.6 mm × 250 mm, manufactured by YMC Inc.) - Eluent: 20 mM aqueous phosphoric acid (pH 2.5)/acetonitrile = 7/3 - Flow rate: 1.0 ml/min - Column temperature: 35°C - Detection wavelength: 210 nm - Optical purity analysis: - Chromatographic column: CHIRALPAK AD-RH (4.6 mm × 150 mm, manufactured by Daicel Chemical Industries, Ltd.) - Elution: 20 mM phosphate buffer (pH 2.5)/acetonitrile = 7/3 - Flow rate: 0.5 ml/min - Column temperature: room temperature - Detection wavelength: 210 nm

References

[1] Inhibition of the uptake of GABA and related amino acids in rat brain slices by the optical isomers of nipecotic acid

(S)-(+)-Nipecotic acid

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