L(-)-Pipecolinic acid
- CAS NO.：3105-95-1
- Empirical Formula: C6H11NO2
- Molecular Weight: 129.16
- MDL number: MFCD00005981
- EINECS: 221-462-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2026-01-21 16:49:52
What is L(-)-Pipecolinic acid?
Chemical properties
white to light yellow crystal powde
The Uses of L(-)-Pipecolinic acid
Pipecolic acid is involved in synaptic transmission in the central nervous system. The l-form occurs in plants.
The Uses of L(-)-Pipecolinic acid
L-Pipecolinic acid is involved in synaptic transmission in the central nervous system. It is also used as pharmaceutical intermediate.
Definition
ChEBI: A pipecolate that is the conjugate acid of L--pipecolic acid.
General Description
Occurs in seeds, malt, edible mushrooms, fruits, etc.
Biochem/physiol Actions
L-pipecolic acid is implicated in Zellweger syndrome. Pipecolic acid is also a plant defence metabolite. It is a signaling compound essential for systemic acquired resistance (SAR).
Preparation
l-Pipecolic acid is an important rigid cyclic nonprotein amino acid, which is obtained through the conversion of l-lysine catalyzed by l-lysine cyclodeaminase (LCD).
Purification Methods
It crystallises from water. The (±)-picrate has m 158-159o (from EtOH or C6H6). [Beilstein 22 H 7, 22 III/IV 97, 22/1 V 220.] The R(+)-enantiomer [1723-00-8] has m 277o(dec) and [] D 20 +27o (c 4, H2O), and the S(-)-enantiomer [3105-95-1] has m 277o(dec) and [] D 20 -26o (c 4, H2O).[cf p 603, Beilstein 22 III/IV 96, 22/1 V 220.]
Properties of L(-)-Pipecolinic acid
| Melting point: | 272 °C(lit.) |
| Boiling point: | 239.22°C (rough estimate) |
| alpha | -27.5 º (c=5, H2O 24 ºC) |
| Density | 1.1426 (rough estimate) |
| refractive index | -27 ° (C=4, H2O) |
| storage temp. | 2-8°C |
| solubility | Water: Soluble |
| form | Fine Crystalline Powder |
| pka | 2.28(at 25℃) |
| color | White |
| optical activity | [α]25/D 26.4°, c = 1 in H2O |
| Water Solubility | soluble |
| Merck | 14,7458 |
| BRN | 81093 |
| CAS DataBase Reference | 3105-95-1(CAS DataBase Reference) |
Safety information for L(-)-Pipecolinic acid
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for L(-)-Pipecolinic acid
| InChIKey | HXEACLLIILLPRG-YFKPBYRVSA-N |
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