ChemicalBook > CAS DataBase List > L-Proline

L-Proline

Product Name
L-Proline
CAS No.
147-85-3
Chemical Name
L-Proline
Synonyms
PRO;H-PRO-OH;L-PRO;l-prolin;(S)-PYRROLIDINE-2-CARBOXYLIC ACID;2-pyrrolidinecarboxylic acid;L-Pro-OH;(2S)-pyrrolidine-2-carboxylic acid;L-Poline;(S)-Prolin
CBNumber
CB6118196
Molecular Formula
C5H9NO2
Formula Weight
115.13
MOL File
147-85-3.mol
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L-Proline Property

Melting point:
228 °C (dec.) (lit.)
alpha 
-85.5 º (c=4, H2O)
Boiling point:
215.41°C (rough estimate)
bulk density
500kg/m3
Density 
1.35
vapor pressure 
0Pa at 25℃
FEMA 
3319 | L-PROLINE
refractive index 
-85 ° (C=4, H2O)
storage temp. 
2-8°C
solubility 
H2O: 50 mg/mL
form 
powder
pka
1.95, 10.64(at 25℃)
color 
White
PH
6.0-7.0 (25℃, 1M in H2O)
Odor
at 100.00 %. odorless
Odor Type
odorless
optical activity
[α]20/D 85.0±1.0°, c = 5% in H2O
biological source
synthetic
Water Solubility 
soluble
Sensitive 
Hygroscopic
λmax
λ: 260 nm Amax: 0.05
λ: 280 nm Amax: 0.05
JECFA Number
1425
Merck 
14,7780
BRN 
80810
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
ONIBWKKTOPOVIA-UHFFFAOYSA-N
LogP
-2.54 at 20℃
CAS DataBase Reference
147-85-3(CAS DataBase Reference)
NIST Chemistry Reference
Proline(147-85-3)
EPA Substance Registry System
L-Proline (147-85-3)
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-22
Safety Statements 
24/25-36/37/39-26
WGK Germany 
3
RTECS 
TW3584000
F 
3-10
TSCA 
Yes
HS Code 
29339990
Hazardous Substances Data
147-85-3(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 5110 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W331902
Product name
L-Proline
Purity
99%, FCC, FG
Packaging
100g
Price
$71
Updated
2024/03/01
Sigma-Aldrich
Product number
W331902
Product name
L-Proline
Purity
99%, FCC, FG
Packaging
1kg
Price
$148
Updated
2024/03/01
Sigma-Aldrich
Product number
W331902
Product name
L-Proline
Purity
99%, FCC, FG
Packaging
5kg
Price
$595
Updated
2024/03/01
Sigma-Aldrich
Product number
P5607
Product name
L-Proline
Purity
from non-animal source, meets EP, USP testing specifications, suitable for cell culture
Packaging
25KG
Price
$9360
Updated
2024/03/01
Sigma-Aldrich
Product number
81709
Product name
L-Proline
Purity
BioUltra, ≥99.5% (NT)
Packaging
10g
Price
$74.5
Updated
2024/03/01
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L-Proline Chemical Properties,Usage,Production

Chemical Properties

L-Proline, an amino acid, is colorless to white crystal or crystalline powder that has a slight, characteristic odor with a slightly sweet taste. It is soluble in water, insoluble in ethanol, diethyl ether and n-butanol, yellow in case of hydrated ninhydrin test solution, glacial acetic acid Red after acidification; pH=6.3, decomposition point is 220-222°C; specific optical rotation [α]20D-85° (0.5-2.0mg/ml, H2O), [α]20D-60.4° (0.5-2.0mg /ml, 5mol/LHCl). It is synthesized from L-glutamine and L-glutamate via L-ornithine in intestine, and from L-ornithine in liver. It is widely used as an ingredient in infusion and infant formula.

Occurrence

Reported found as a component in many proteins; also widely occurring as the free acid in natural products. A major constituent of collagen, the main fibrous protein found in bone, cartilage and other connective tissue.

Uses

L-Proline is used as asymmetric catalysts in organic synthesis and asymmetric aldol cyclization. It is involved in the Michael addition of dimethyl malonate to alfa-beta-unsaturated aldehydes. It is a precursor of hydroxyproline in collagen. It is an active component of collagen and involved in the proper functioning of joints and tendons. It finds uses in pharmaceutical, biotechnological applications due to its osmoprotectant property. Further, it is used with ninhydrin in the chromatography.

Uses

L-Proline is an amino acid and precursor (with vitamin C) for collagen, the building block of the structure of tendons, ligaments, arteries, veins and muscles. It is important in wound healing.

Preparation

Synthesis of L-proline: Using glutamic acid as a raw material, it is esterified with absolute ethanol under the catalysis of sulfuric acid, and triethanolamine is added to free the aminosulfate to obtain glutamic acid-δ-ethyl ester. The glutamic acid-δ-ethyl ester is then reduced with a metal reducing agent potassium borohydride to obtain crude proline, which is finally separated and purified to obtain crude L-proline.

Definition

ChEBI: L-proline is pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. It has a role as a micronutrient, a nutraceutical, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and a member of compatible osmolytes. It is a glutamine family amino acid, a proteinogenic amino acid, a proline and a L-alpha-amino acid. It is a conjugate base of a L-prolinium. It is a conjugate acid of a L-prolinate. It is an enantiomer of a D-proline. It is a tautomer of a L-proline zwitterion.

Biotechnological Production

Direct fermentation using analogue-resistant mutants of coryneform bacteria or Serratia marcescens is an economic production method. An isoleucine auxotrophic mutant of Brevibacterium flavum having resistance to sulfaguanidine and D,L-3,4-dehydroproline (DP) is able to accumulate 40 g/L L-proline. Brevibacterium flavum AP113 is claimed to produce 97.5 g/L L-proline; this mutant is characterized by isoleucine auxotrophy, resistance to DP, and osmotic pressure and incapable to degrade Lproline. A proline oxidase-less strain of Serratia marcescens, having resistance to DP, thiazoline-4-carboxylate and azetidine-2-carboxylate, overproduces 58.5 g/L L-proline into the culture medium. By amplification of the genes proA and proB in this type of regulatory mutant, a construct was obtained which yields 75 g/L L-proline.

benefits

L-proline is considered a non-essential amino acid as it can be synthesised from arginine via the urea cycle in liver, and from glutamine/glutamic acid in the intestinal epithelium. It has a number of beneficial properties including connective tissue strengthening, Stronger Connective Tissue, Decreased Risk Of Heart Disease, Maintenance Of Muscle Tissueand skin health.

General Description

L-Proline is a non-essential amino acid, which is a building block of proteins. Peptides bond to proline, making it a useful building block for proteins. It can be used as a cell culture media component for the commercial biomanufacturing of therapeutic recombinant proteins and monoclonal antibodies. L-Proline plays important roles in various biological processes. It is involved in the synthesis of collagen, which is one of the most abundant proteins in the human body and provides structural support to tissues such as skin, bone, cartilage, and tendons.

Biochem/physiol Actions

Proline is a cyclic, non-essential, hydrophobic amino acid. It is a proteinogenic amino acid which is crucial for primary metabolism. In peptide chains, proline residues confer structural constraints and enhance the susceptibility of proximal peptide bonds to protease activity.

Side effects

The only known side effects are reactions from taking too much L-proline, like all amino acids. It causes toxicity levels and amino acid imbalances in your body.

Purification Methods

A likely impurity is hydroxyproline. Purify L-proline via its picrate which is crystallised twice from water, then decomposed with 40% H2SO4. The picric acid is extracted with diethyl ether, the H2SO4 in solution is precipitated with Ba(OH)2, and the filtrate is evaporated. The residue is crystallised from hot absolute EtOH [Mellan & Hoover J Am Chem Soc 73 3879 1951] or EtOH/Et2O. Its solubility in H2O is >100%. It sublimes at 182-187o/0.3mm with 99.4% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. It is hygroscopic and is stored in a desiccator. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2178-2199 1961, Beilstein 22 III/IV 8, 22/1 V 31.]

Structure and conformation

L-proline, also known as L-pyrrolidine-2-carboxylic acid, is a neutral amino acid. Although proline is classified as an amino acid, it is strictly speaking an imino acid, since it contains an imino group (carbon-nitrogen double bond). Due to its cyclic pyrrolidine side chain it is classified as a nonpolar aliphatic amino acid.

L-Proline Preparation Products And Raw materials

Raw materials

PICRIC ACID D(+)-Glucose L-Glutamic acid Hydrolyzate Triethylamine Ion exchange resin column Ammonium chloride Potassium borohydride Chromatography Casein Isopropyl alcohol Gelatin Triethanolamine Aluminum oxide

Preparation Products

D-(S)-3-acetylthio-2-methylpropionylL-proline R(-)-DENOPAMINE Enalapril D-Proline (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole DL-Proline Levosulpiride 2-Fluoro-4-(methylsulfonyl)aniline (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Lisinopril Captopril 2-(2-Aminoethyl)-1-methylpyrrolidine (S)-2-Methylproline
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View Lastest Price from L-Proline manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
L-Proline 147-85-3
Price
US $99.00-35.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-10
Hebei Saisier Technology Co., LTD
Product
L-Proline 147-85-3
Price
US $6.00/KG
Min. Order
1KG
Purity
More than 99%
Supply Ability
2000KG/MONTH
Release date
2024-04-18
Hebei Saisier Technology Co., LTD
Product
L-Proline 147-85-3
Price
US $6.00/KG
Min. Order
1KG
Purity
More than 99%
Supply Ability
2000KG/MONTH
Release date
2024-04-18

147-85-3, L-ProlineRelated Search:

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