CAS 147-85-3 L-Proline - Catalysts / Alfa Chemistry

Synonyms

2-Pyrrolidinecarboxylic acid

IUPAC Name

(2S)-Pyrrolidine-2-carboxylic acid

Molecular Weight

115.13

Molecular Formula

C5H9NO2

Canonical SMILES

C1CC(NC1)C(=O)O

InChI

InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1

InChI Key

ONIBWKKTOPOVIA-BYPYZUCNSA-N

Boiling Point

215.41 °C

Melting Point

228 °C(lit.)

Flash Point

106.3 °C

Purity

99%

Density

1.35 g/cm³

Solubility

Soluble in water

Appearance

White powder

Storage

2-8 °C

Assay

0.99

Color Form

Flat needles from alcohol + ether; prisms from water;White crystals or crystalline powder;

Complexity

103

Covalently-Bonded Unit Count

Decomposition

When heated to decomposition it emits toxic vapors of /nitrogen oxides/.;

Defined Atom Stereocenter Count

EC Number

205-702-2

Exact Mass

115.063328530

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Isomeric SMILES

C1C[C@H](NC1)C(=O)O

Monoisotopic Mass

115.063328530

NSC Number

760114

Odor

Odorless;

Other Experimental

Isoelectric point: 6.30;Colorless crystals. Soluble in water and alcohol; insoluble in ether; optically active. /Proline/;MP: 215-220 deg C with decomposition /D(+)-Proline/;MASS: 76286 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 4037 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63) /D-Proline/;MASS: 4037 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63) /DL-Proline/;MP: 205 deg C with decomposition /DL-Proline/;Monohydrate, crystals. MP 190 deg C (when anhydrous, decomposes at 205 deg C). Soluble in water, alcohol; sparingly soluble in acetone, chloroform, benzene; insoluble in ether /DL-Proline/;Henry's Law constant = 1.92X10-9 atm-cu m/mol at 25 deg C (est);Hydroxyl radical reaction rate constant = 8.28X10-11 cu cm/molec-sec at 25 deg C (est);

Physical State

Solid

Rotatable Bond Count

Stability

Stable. Incompatible with strong oxidizing agents.

Topological Polar Surface Area

49.3 Å²

UNII

9DLQ4CIU6V

Vapor Pressure

3.02X10-8 mm Hg at 25 deg C (est);

Application

L-Proline serves a crucial role as an amino acid and a precursor for collagen, which is fundamental in constructing tendons, ligaments, arteries, veins, and muscles. This colorless to white crystalline powder has a mild, characteristic odor and a slightly sweet taste. It dissolves in water but remains insoluble in ethanol, diethyl ether, and n-butanol, and exhibits a pH of 6.3 with a decomposition point between 220-222°C. Synthesized from L-glutamine and L-glutamate via L-ornithine in the intestine and from L-ornithine in the liver, L-Proline is widely used in infusion solutions and infant formulas. It acts as an asymmetric catalyst in organic synthesis and participates in the Michael addition of dimethyl malonate to alfa-beta-unsaturated aldehydes. As an essential component of hydroxyproline in collagen, it supports joint and tendon health. L-Proline is significant in wound healing and offers osmoprotectant properties beneficial for pharmaceutical and biotechnological applications. Additionally, it plays a role in chromatographic analysis with ninhydrin and serves as a cell culture media component in biomanufacturing of therapeutic recombinant proteins and monoclonal antibodies. In biological contexts, L-Proline is vital for synthesizing collagen, a protein crucial for skin, bone, cartilage, and tissue structural integrity.

December 11, 2024

Efficient and Versatile Catalyst for Research

L-Proline was excellent in our lab's asymmetric syntheses. Its catalytic properties in aldol reactions enhanced efficiency, and its role in collagen synthesis supported our biomaterial studies. Highly recommended for its versatility in biochemical research.