Basic information
- CAS
3105-95-1- Standard SMILES
O=C(O)[C@@H]1CCCCN1- InChIKey
HXEACLLIILLPRG-YFKPBYRVSA-N- Molecular formula
- C6H11NO2
- Average molar mass
- 129.16 g/mol
- Monoisotopic mass
- 129.07897859
Overview
L-pipecolic acid is the L-enantiomer of pipecolic acid. It is a metabolite of lysine. It has a role as a plant metabolite and a human metabolite. It is a conjugate acid of a L-pipecolate. It is an enantiomer of a D-pipecolic acid. It is a tautomer of a L-pipecolic acid zwitterion.
Names & identifiers
- Preferred name
- Pipecolic acid, (-)-
- IUPAC
- (2S)-piperidine-2-carboxylic acid
- English name
- L(-)-Pipecolinic acid
- Molecular formula
- C6H11NO2
- Molecular weight
- 129.16
Names & synonyms
l-Pipecolic acid(S)-Piperidine-2-carboxylic acidL-Homoproline(2S)-piperidine-2-carboxylic acidL-Pipecolinic acid2-Piperidinecarboxylic acid, (2S)-Pipecolic acid, (-)-(S)-pipecolic acid(-)-Pipecolic acidL-(-)-pipecolic acid(S)-(-)-pipecolic acid(S)-Pipecolinic acid
Show more names
h-pip-ohL-PIPECOLATEHOMOPROLINEL-(-)-PIPECOLINIC ACIDL-2-Pipecolinic acidPIP-OH(S)-2-PIPERIDINECARBOXYLIC ACID
Pipecolic acid, L-(-)-EINECS 221-462-1NSC 93089Pipecolic acid, L-(-)-PIPECOLINIC ACIDCHEBI:30913DTXSID401035840PIPECOLIC ACID L-FORM [MI]
Database identifiers
- CAS
3105-95-1- PubChem CID
- 439227
- DTXSID
DTXSID401035840- ChEMBL
CHEMBL322883- ChEBI
CHEBI:30913- UNII
- 69374CKB33
- EC Number
- 221-462-1
- Nikkaji
- J215.717I
Properties
Computed structural properties
- XLogP
- -2.3
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 114
Experimental & physicochemical properties
Melting Point272 °C
Physical DescriptionSolid
Collision Cross Section
126.71 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
133.82 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
128.9 Ų [M-H]-
Physicochemical properties
- Melting point
- 272 °C · 272 °C(lit.)
- alpha
- -27.5 · -27.5 º (c=5, H2O 24 ºC)
- Boiling point
- 239.22 °C · 239.22°C (rough estimate)
- Density
- 1.1426 · 1.1426 (rough estimate)
- refractive index
- -27 ° · -27 ° (C=4, H2O)
- storage temp.
- 2 · 2-8°C
- solubility
- Water: Soluble
- pka
- 2.28 · 2.28(at 25℃)
- form
- Fine Crystalline Powder
- color
- White
- optical activity
- 25 · [α]25/D 26.4°, c = 1 in H2O
- Water Solubility
- soluble
- Merck
- 14 · 14,7458
- BRN
- 81093 · 81093
- InChI
- 1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1
- InChIKey
- HXEACLLIILLPRG-YFKPBYRVSA-N
- SMILES
- OC(=O)[C@@H]1CCCCN1
- CAS DataBase Reference
- 3105 · 3105-95-1(CAS DataBase Reference)
- FDA UNII
- 69374 CKB33 · 69374CKB33
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 26 · NA.26
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 302 · P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-24/25
- WGK Germany
- 3 · 3
- TSCA
- No
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- No
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-24/25
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Tissue LocationsLiver
Cellular LocationsPeroxisome
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria
Applications
DescriptionL-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.
UsesL-Pipecolinic acid is involved in synaptic transmission in the central nervous system. It is also used as pharmaceutical intermediate.
UsesPipecolic acid is involved in synaptic transmission in the central nervous system. The l-form occurs in plants.
General DescriptionOccurs in seeds, malt, edible mushrooms, fruits, etc.
Upstream & downstream products
Downstream products
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes
DefinitionChEBI: A pipecolate that is the conjugate acid of L--pipecolic acid.
Related reactions
21 records
Compound notes
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