L-pipecolate

Base Information

• Chemical Name: L-pipecolate
• CAS No.: 3105-95-1
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 29339900
• Mol file: 3105-95-1.mol

Synonyms:L-pipecolate;(S)-pipecolate;L-pipecolic acid zwitterion;CHEBI:61185;(2S)-piperidinium-2-carboxylate;dl-homoproline, dl-pipecolic acid;(S)-2-carboxypiperidinium betaine

Chemical Property of L-pipecolate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.0026mmHg at 25°C
• Melting Point: 272 °C(lit.)
• Refractive Index: -27 ° (C=4, H2O)
• Boiling Point: 265.766 °C at 760 mmHg
• PKA: 2.28(at 25℃)
• Flash Point: 114.532 °C
• PSA: 49.33000
• Density: 1.125 g/cm³
• LogP: 0.54190
• Storage Temp.: Store at RT.
• Water Solubility.: soluble
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 108

Purity/Quality:

98% Min ^*data from raw suppliers

L-Pipecolic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC[NH2+]C(C1)C(=O)[O-]
• Isomeric SMILES: C1CC[NH2+][C@@H](C1)C(=O)[O-]
• Description: 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.
• Uses: Pipecolic acid is involved in synaptic transmission in the central nervous system. The l-form occurs in plants. L-Pipecolinic acid is involved in synaptic transmission in the central nervous system. It is also used as pharmaceutical intermediate.

Technology Process of L-pipecolate

There total 99 articles about L-pipecolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

(3S,5S)-2,3,5,6-tetrahydro-3-(4-bromobutyl)-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazine-2-one (625824-32-0) → L-Norleucine (327-57-1) + pipecolinic acid (3105-95-1,83680-83-5)

Guidance literature:

With hydrogen; trifluoroacetic acid; palladium on activated charcoal; In methanol; for 24h; under 2844.31 Torr;

DOI:10.1081/SCC-120021497

Reference yield: 9.0%

(2S,3'S,5'R,6'R)-6'-(3-Carboxy-propyl)-[2,3']bipiperidinyl-5'-carboxylic acid (117614-90-1) → pipecolinic acid (3105-95-1,83680-83-5) + 3-amino propanoic acid (107-95-9) + 4-amino-n-butyric acid (56-12-2)

Guidance literature:

With chromium(VI) oxide; In sulfuric acid; at 100 ℃; for 6h;

DOI:10.1139/v88-280

Reference yield:

ulleungamide A → L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + (S)-2-isopropylsuccinic acid (1187-70-8) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) + 5-hydroxy-6-methyl-2,3-dehydropipecolic acid + N-methyl-D-phenylalanine (56564-52-4) + (2S,4R)-4-hydroxypiperidine-2-carboxylic acid (1844-40-2,175671-49-5,189385-64-6) + glycine (56-40-6,18875-39-3,25718-94-9) + pipecolinic acid (3105-95-1,83680-83-5)

Guidance literature:

With hydrogenchloride; at 100 ℃; for 1h;

DOI:10.1021/acs.orglett.5b01969

upstream raw materials:

pipecolic Acid

(2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid

2-Picolinic acid

L-lysine

Downstream raw materials:

(2S)-N-benzoyl-2-piperidinecarboxylic acid

(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid

(2R,3R)-3-hydroxypiperidine-1-carboxylic acis

(2S,5R)-5-hydroxy-2-piperidinecarboxylic acid

Refernces

• 1、 Chandren, Sheela,Ohtani, Bunsho. "Preparation and reaction of titania particles encapsulated in hollow silica shells as an efficient photocatalyst for stereoselective synthesis of pipecolinic acid". . p. 677 - 679. Retrieved 2012.
• 2、 Fujii, Tadashi,Mukaihara, Manabu,Agematu, Hitosi,Tsunekawa, Hiroshi. "Biotransformation of L-lysine to L-pipecolic acid catalyzed by L-lysine 6-aminotransferase and pyrroline-5-carboxylate reductase". . p. 622 - 627. Retrieved 2002.
• 3、 -. "Preparation method of caine drug intermediate (S)-2-piperidinecarboxylic acid". . . Retrieved 2021/06/22.
• 4、 Benítez-Mateos, Ana I.,Calvey, Liam,Paradisi, Francesca,Roura Padrosa, David. "Cell-free biocatalytic syntheses of l-pipecolic acid: A dual strategy approach and process intensification in flow". . p. 5310 - 5316. Retrieved 2020/09/17.