(2S)-pyrrolidine-2-carboxylic acid

• ChemBase ID: 57
• Molecular Formular: C5H9NO2
• Molecular Mass: 115.13046
• Monoisotopic Mass: 115.06332853
• SMILES: OC(=O)[C@H]1NCCC1
• Canonical SMILES: OC(=O)[C@@H]1CCCN1
• InChI: InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
• InChIKey: ONIBWKKTOPOVIA-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: L-proline
• Synonyms: 2-Pyrrolidine carboxylic acid; L-(-)-proline; H-Pro-OH; 2-Pyrrolidinecarboxylic acid; (S)-Proline; (S)-2-Pyrrolidinecarboxylic acid; (S)-2-Carboxypyrrolidine; (-)-Proline; (-)-2-Pyrrolidinecarboxylic acid; L-Proline; L-PROLINE, U.S.P.; (S)-Pyrrolidine-2-carboxylic acid; L-Proline; Proline; 2-Pyrrolidinecarboxylic acid; L-Proline; (2S)-pyrrolidine-2-carboxylic acid; (S)-吡咯烷-2-羧酸; L-脯氨酸

Database IDs

• CAS Number: 147-85-3
• EC Number: 205-702-2
• MDL Number: MFCD00064318
• Beilstein Number: 80810
• Merck Index: 147780
• PubChem SID: 46506858; 160963520; 24898677; 24887886; 24901637; 24898097; 24887885; 24898986
• PubChem CID: 145742
• FEMA ID: 3318
• Council of Europe Number: 10378
• Flavis Number: 17.019

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.9406707
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.5687168
• LogD (pH = 7.4): -2.5686643
• Log P: -2.5686383
• Molar Refractivity: 28.0643 cm^3
• Polarizability: 11.294152 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.71
• LOG S: 0.5
• Solubility (Water): 3.65e+02 g/l

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 M at 20 °C, clear, colorless; H2O: soluble50 mg/mL; Soluble
• Apperance: powder; Powder
• Melting Point: 220-222°C; 228 °C (dec.)(lit.); ca 225°C dec.
• Density: 1.36
• Optical Rotation: [α]20/D -84.5±1°, c = 5% in H2O; [α]20/D -84°, c = 4 in H2O; [α]20/D -85.0±1.0°, c = 5% in H2O; -84 (c=1 in water)
• Absorption Wavelength: λ: 260 nm Amax: 0.05; λ: 280 nm Amax: 0.05
• Hydrophobicity(logP): -2.4; -2.413
• pH: 6.0-7.0 (20 °C, 1 M in H2O); 6.0-7.0 (25 °C, 1 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic; IRRITANT
• RTECS: TW3584000
• German water hazard class: 1
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

Product Information

• Purity: ≥99%; >99% (TLC); ≥98.5%; ≥99%; ≥99% (TLC); ≥99.0%; ≥99.0% (NT); ≥99.5% (NT); 95%; 95+%; 97%; 98%; 99%
• Grade: certified reference material; EP; Halal; Kosher; NI; ReagentPlus®; SAJ special grade; TraceCERT®; USP
• Optical Purity: ee: 98% (GLC)
• Suitability: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: <0.1%; ≤0.1%; ≤0.1% (as SO4)
• Impurities: <0.0005% Phosphorus (P); <0.1% Insoluble matter; ≤0.3% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test; L-Hydroxyproline, free
• Cation Traces: Al: <0.0005%; Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: <0.0005%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: <0.0005%; Cu: ≤5 mg/kg; Fe: <0.0005%; Fe: ≤5 mg/kg; K: <0.005%; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: <0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: <0.005%; Na: ≤50 mg/kg; NH4+: <0.05%; NH4+: ≤20 mg/kg; Ni: ≤5 mg/kg; Pb: <0.001%; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: <0.0005%; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): <0.05%; chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): <0.05%; sulfate (SO42-): ≤100 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.1% loss on drying, 20 °C (HV); ≤0.2% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA
• λ: 1 M in H2O
• Product Line: BioUltra; BioXtra
• abs.: A1M/260, H2O <0.05; A1M/280, H2O <0.05
• Empirical Formula (Hill Notation): C5H9NO2

DETAILS

MP Biomedicals - 05217149

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02194728

Cell Culture Reagent
Crystalline
Purity: 99+%
Hydroxy-_L -proline free

MP Biomedicals - 02199543

Solid

MP Biomedicals - 02102730

Crystalline
Purity: 99+%
Hydroxy-L-proline free

DrugBank - DB00172

• Drug Groups: approved; nutraceutical
• Description: A non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. [PubChem]
• Indication: L-Proline is extremely important for the proper functioning of joints and tendons and also helps maintain and strengthen heart muscles.
• Pharmacology: L-Proline is a major amino acid found in cartilage and is important for maintaining youthful skin as well as repair of muscle, connective tissue and skin damage. It is also essential for the immune system, and for necessary balance of this formula. It is an essential component of collagen and is important for proper functioning of joints and tendons. L-Proline is extremely important for the proper functioning of joints and tendons. Helps maintain and strengthen heart muscles.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• External Links: Wikipedia

Sigma Aldrich - 81710

Other Notes
Proline-catalyzed asymmetric Robinson annelation1; Asymmetric self-condensation of β-ionylideneacetaldehyde, retinal and related compounds2

Sigma Aldrich - P8865

Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - 81709

Other Notes
Protects enzymes against heat inactivation1; Growth requirement of various microorganisms2

Sigma Aldrich - 131547

Application
Catalyst for enantioselective reduction of ketones.1 Ligand used in TLC resolution of amino acids.2 Synthon for dolaproine and related diastereomers.3

Sigma Aldrich - W331902

Packaging
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in fiber drum

Sigma Aldrich - 93693

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - P0380

Packaging
1 kg in poly bottle
10 mg in autosmp vl
100 g in poly bottle
5 kg in poly drum
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• For use as a catalyst in an asymmetric aldol cyclization, see: Org. Synth. Coll., 7, 363 (1990). For reaction scheme, see 2-Methylcyclopentane-1,3-dione, A13936. For use in a direct enantioselective crossed aldol reaction with aldehydes, see: J. Am. Chem. Soc., 124, 6798 (2002). For use as an organoctalyst in direct aldol reactions of ɑ-oxyaldehydes, as the first step in a two-step synthesis of carbohydrates, see: Angew. Chem. Int. Ed., 43, 2152 (2004). Mediates the enantioselective borane reduction of ketones to chiral alcohols with moderate to good ee: Monatsh. Chem., 131, 91 (2000). Also used to induce high ee in the ɑ-amination of aldehydes with Dibenzyl azodicarboxylate, L19347: J. Am. Chem. Soc., 124, 5656 (2002), or Diethyl azodicarboxylate, L19348: Angew. Chem. Int. Ed., 41, 1790 (2002).
• For a review of the use of proline as a chiral catalyst, see: Synlett, 1675 (2001); Synlett, 1973 (2006).
• For preparation from L-proline of the chiral hydrazone "SAMP", and enantioselective syntheses using the RAMP/ SAMP methodology, see: Org. Synth. Coll., 8, 26, 403 (1985).
• For formation of a fused pyrrolidino-oxazolidinone, and use of the product in a synthesis of enantiopure ɑ-branched amino acids, see: Org. Synth. Coll., 9, 626 (1998); for reaction scheme, see Trimethylacetaldehyde, A15013.
• The Li salt has been used as a catalyst for the Michael addition of dimethyl malonate to ɑ?-unsaturated aldehydes: J. Chem. Soc., Chem. Commun., 1088 (1991).