| Identification | More | [Name]
(S)-2-PIPERIDINONE-6-CARBOXYLIC ACID | [CAS]
34622-39-4 | [Synonyms]
6-OXO-L-PIPECOLIC ACID
H-L-PON-OH
L-6-OXO-PIPECOLINIC ACID
L-PYROHOMOGLUTAMIC ACID
PYRO-L-ALPHA-AMINOADIPIC ACID
(S)-2-PIPERIDINONE-6-CARBOXYLIC ACID
(S)-2-PIPERIDONE-6-CARBOXYLIC ACID
(S)-6-OXO-2-PIPERIDINECARBOXYLIC ACID
(S)-6-OXO-PIPERIDINE-2-CARBOXYLIC ACID
6-Oxo-L-pipecolic acid, (S)-2-Piperidone-6-carboxylic acid, L-Pyrohomoglutamic acid | [Molecular Formula]
C6H9NO3 | [MDL Number]
MFCD03839863 | [Molecular Weight]
143.14 | [MOL File]
34622-39-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
129-134 °C
| [Boiling point ]
437.0±38.0 °C(Predicted) | [density ]
1.286±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Aqueous Acid (Sparingly, Heated, Sonicated), DMSO (Slightly, Heated) | [form ]
Solid | [pka]
3.59±0.20(Predicted) | [color ]
White to Pale Brown | [InChI]
InChI=1S/C6H9NO3/c8-5-3-1-2-4(7-5)6(9)10/h4H,1-3H2,(H,7,8)(H,9,10)/t4-/m0/s1 | [InChIKey]
FZXCPFJMYOQZCA-BYPYZUCNSA-N | [SMILES]
N1C(=O)CCC[C@H]1C(O)=O | [CAS DataBase Reference]
34622-39-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [HS Code ]
2933790090 |
| Hazard Information | Back Directory | [Uses]
6-Oxo-L-pipecolic Acid is an intermediate in the synthesis of metabolites of lysine developed during aging and in diabetic patients. | [Synthesis]
General procedure for the synthesis of (S)-2-piperidone-6-carboxylic acid from L-2-aminoadipic acid:
(a) Mix (S)-2-aminoadipic acid (50 g, 310.25 mmol), acetic acid (100 mL) and water (400 mL) and reflux for 3 hours. The unreacted starting amino acid (24 g) was filtered, the filtrate was evaporated, and the residue was dissolved in hot water (50 mL) and precipitated as crystals after cooling. The crystals were collected by filtration to afford the title intermediate (S)-6-oxopiperidine-2-carboxylic acid (20 g, 45% yield). | [References]
[1] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 11, p. 1525 - 1531
[2] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450
[3] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1654 - 1658
[4] Chemical Communications, 2010, vol. 46, # 9, p. 1413 - 1415
[5] Patent: US2013/287731, 2013, A1. Location in patent: Paragraph 0295; 0296 |
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