L(-)-Pipecolinic acid

Iupac Name：(2S)-piperidine-2-carboxylic acid

Molecular Weight：129.16

Modify Date.: 2022-10-31 16:30

Introduction: L-Pipecolinic acid is involved in synaptic transmission in the central nervous system. It is also used as pharmaceutical intermediate. It is a lysine metabolite; defect in its catabolism is involved in hyperpipecolic acidemia, cerebro-hepato-renal syndrome, neonatal onset adrenoleukodystrophy, and infantile Refsum disease. It can be associated with some forms of epilepsy. CRYM, a taxon-specific crystallin protein that also binds thyroid hormones, is involved in the pipecolic acid pathway. View more+

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1. Names and Identifiers

1.1 Name: L(-)-Pipecolinic acid
1.2 Synonyms: (-)-Pipecolic acid (-)-Pipecolinic acid (2S)-2-Piperidinecarboxylic acid (2S)-Piperidin-1-ium-2-carboxylate (2S)-Piperidine-2-carboxylic acid (S)-(-)-2-PIPERIDINECARBOXYLIC ACID (S)-(-)-PIPECOLIC ACID (S)-(-)-Piperidine-2-carboxylic acid (S)-2-PIPERIDINECARBOXYLIC ACID (S)-PIPECOLIC ACID (S)-Pipecolinic acid (S)-PIPERIDINE-2-CARBOXYLIC ACID 2-Piperidinecarboxylic acid (2S)- 2-Piperidinecarboxylic acid, (2S)- 2-Piperidinecarboxylic acid, (S)- H-L-Pip-OH H-Pip-OH L-(-)-Pipecolic acid L-Homoproline L-Pipecolic acid L-Pipecolinic Acid L-Piperidine-2-carboxylic acid NSC 93089 Pipecolic acid, (S)-(-)- PIP-OH RARECHEM BK PT F201 S-(-)-PIPECOLINIC ACID

1.3 CAS No.: 3105-95-1

1.4 CID: 439227

1.5 EINECS(EC#): 221-462-1

1.6 Molecular Formula: C6H11NO2 (isomer)

1.7 Inchi: InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1

1.8 InChkey: HXEACLLIILLPRG-YFKPBYRVSA-N

1.9 Canonical Smiles: C1CCNC(C1)C(=O)O

1.10 Isomers Smiles: C1CCN[C@@H](C1)C(=O)O

2. Properties

2.1 Density: 1.1426 (rough estimate)

2.1 Melting point: 272 °C(lit.)

2.1 Boiling point: 239.22°C (rough estimate)

2.1 Refractive index: -27 ° (C=4, H2O)

2.1 Flash Point: 114.5 °C

2.1 PSA: 52.16

2.1 logP: 0.54190

2.1 Appearance: white to light yellow crystal powde

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: white to light yellow crystal powde

2.4 Color/Form: White to Yellow Solid

2.5 pKa: 2.28(at 25℃)

2.6 Water Solubility: Soluble in water

2.7 Stability: Stable under normal temperatures and pressures.

2.8 StorageTemp: Store at RT.

3. Use and Manufacturing

3.1 Definition: ChEBI: A pipecolate that is the conjugate acid of L--pipecolic acid.

3.2 Usage: Pipecolic acid is involved in synaptic transmission in the central nervous system. The l-form occurs in plants.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: 36/37/38

4.1 Safety Statements: 26-36-24/25

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. 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	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

7. Synthesis Route

3105-95-1Total: 5 Synthesis Route

98-98-6 373 Suppliers

3105-95-1 227 Suppliers

1723-00-8 160 Suppliers

Literatures:
Tetrahedron Letters, , vol. 31, # 16 p. 2341 - 2344
Yield: null

56-87-1 449 Suppliers

3105-95-1 227 Suppliers

1723-00-8 160 Suppliers

Literatures:
Chemical Physics Letters, , vol. 242, # 3 p. 315 - 319
Yield: null

4043-87-2 157 Suppliers

3105-95-1 227 Suppliers

1723-00-8 160 Suppliers

Literatures:
Chemistry of Materials, , vol. 23, # 5 p. 1280 - 1287
Yield: null

View all

8. Other Information

8.0 Usage: L-Pipecolinic acid is involved in synaptic transmission in the central nervous system. It is also used as pharmaceutical intermediate.

9. Computational chemical data

Molecular Weight: 129.16g/mol
Molecular Formula: C₆H₁₁NO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 129.078978594
Monoisotopic Mass: 129.078978594
Complexity: 114
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 49.3
Heavy Atom Count: 9
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: AAADccBiMAAAAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAAAAAAAHgAQCAAACCjBgAQACALAAgAIAACQCAAAAAAAAAAAAIGIAAACABIAgCAEQAAEEACQAAGYSAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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