Encyclopedia / Vitamins, Amino Acids and Coenzymes / Pharmaceutical Intermediates / Organic Intermediate

L-Proline

CAS：147-85-3
MW:115.13
MF：C5H9NO2

amino acid, nutrient

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: L-Proline

1.2 Synonyms: (−)-(S)-proline; (−)-2-pyrrolidinecarboxylic acid; (−)-proline; (-)-(S)-proline; (-)-2-Pyrrolidinecarboxylic acid; (-)-Proline; (2S)-2-Pyrrolidinecarboxylic acid; (2S)-proline; (2S)-pyrrolidine-2-carboxylic acid; (l)-proline; (S)-(-)-Proline; (S)-(-)-Pyrrolidine-2-carboxylic acid; (S)-2-Carboxypyrrolidine; (S)-proline; (S)-Pyrrolidine-2-carboxylic acid; (S)-Pyrrolidine-2-carboxylic acid,L-Proline; 2-Pyrrolidinecarboxylic acid; 2-Pyrrolidinecarboxylic acid, (S)-; 2-Pyrrolidinecarboxylicacid; BYL719; EINECS 205-702-2; EINECS 210-189-3; L-(-)-proline; L(-)-Proline; L-(-)-PROLINE ((S)-(-)-PROLINE); L(-)-Proline 0; L-a-Pyrrolidinecarboxylic Acid; l-Pro; L-Proline ,L-2-Pyrrolidinecarboxylic acid; L-PROLINE, NATURAL; L-PROLINE, SYNTHETIC; L-pyrrolidine-2-carboxylic acid; MFCD00064318; Proline; Proline, L-; pyrrolidine-2-carbonic acid; QCR-1;

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1.3 CAS No.: 147-85-3

1.4 CID: 145742

1.5 EINECS: 205-702-2

1.6 Molecular Formula: C5H9NO2

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

1.8 InChkey: ONIBWKKTOPOVIA-BYPYZUCNSA-N

1.9 Canonical Smiles: C1CC(NC1)C(=O)O

1.10 Isomers Smiles: C1C[C@H](NC1)C(=O)O

2. Properties

2.1 Solubility: H2O: 50?mg/mL

2.2 AnalyticLaboratory Methods: AOAC method 960.47, Amino Acids in Vitamin Preparations; microbiological method using basal media /amino acids/

2.3 Appearance: White crystalline powder

2.4 Storage: Hygroscopic. Ambient temperatures.

2.5 Chemical Properties: White crystalline powder

2.6 Color/Form: Powder

2.7 Decomposition: When heated to decomposition it emits toxic vapors of /nitrogen oxides/.

2.8 Odor: Odorless

2.9 PH: 6.0-7.0 (25℃, 1M in H2O)

2.10 Physical: Withheld

2.11 pKa: 1.95, 10.64(at 25℃)

2.12 Water Solubility: soluble

2.13 Spectral Properties: SPECIFIC OPTICAL ROTATION: -80.9 DEG @ 20 DEG C/D (WATER, 1%); SADTLER REF NUMBER: 1905 (IR, PRISM)
SPECIFIC OPTICAL ROTATION: -85.0 @ 23.4 DEG C/D (WATER, 1%); -52.6 @ 20 DEG C/D (0.50 N HYDROCHLORIC ACID, 0.58%); -93.9 DEG @ 20 DEG C/D (0.6 N POTASSIUM HYDROXIDE, 2.4%)
IR: 21030 (Sadtler Research Laboratories IR Grating Collection)
UV: 6-52 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 7565 (Sadtler Research Laboratories Spectral Collection)
MASS: 4037 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)

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2.14 Stability: Stable. Incompatible with strong oxidizing agents.

2.15 StorageTemp: 2-8°C

2.16 Toxicity Summary: IDENTIFICATION AND USE: L-Proline; is a solid. It is used in biochemical and nutritional research, microbiological tests, culture media, as a laboratory reagent, and dietary supplement. It is also used in pharmaceutical preparations for injection or infusion. HUMAN EXPOSURE AND TOXICITY: There are no data available. ANIMAL STUDIES: In a 30-day study, a group of seven female rats were given L-proline; at a dose of 50 mg/kg bw per day in water;. A group of 10 rats served as the control group. After 30 days, all animals were weighed, necropsied, and subjected to a complete gross examination. Histopathology and microscopic examinations of the liver and kidneys were conducted. Samples of serum were obtained for determination of enzyme activities, and concentrations of creatinine; and total protein. There were no treatment-related effects in rats given L-proline; at 50 mg/ kg bw per day compared with the controls. Of 20 common amino acids only proline enhanced formation of mutagenic activity measured in S typhimurium TA98 with rat liver microsomes. In the assay for reverse mutation in Salmonella typhimurium, negative results were reported for L-proline; at concentrations of up to 1000 mg/mL, with and without metabolic activation, in several strains of S. typhimurium (TA92, TA97, TA98, TA100, TA102, TA1530, TA1531, TA1532, TA1535, TA1537, TA1538, and TA1964). ECOTOXICITY STUDIES: Proline-treated plants showed high antioxidant enzymes activities (superoxide dismutase, catalase and glutathione; peroxydase) in roots and leaves as compared to Cd-treated plants. Proline plays an important role in plant response to various environmental stresses. For example, proline supplementation alleviated the deleterious effects of young olive plants exposed to Cd stress.

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3. Use and Manufacturing

3.1 Description: L-Proline (CAS 147-85-3) is a non-essential amino acid that plays a crucial role in protein synthesis and collagen production. It is a white crystalline powder with a molecular formula of C5H9NO2. L-Proline is highly soluble in water, forming a clear solution. It has a melting point of 228-232°C and a boiling point of 214-216°C. This chemical is stable under normal conditions and is both odorless and tasteless.

Applicable Fields
L-Proline has various applications in different fields:

Pharmaceutical Industry: L-Proline is widely used in the pharmaceutical industry as a building block for the synthesis of peptides and proteins. It is an essential component in the production of drugs, such as antibiotics, antiviral agents, and immunosuppressants. L-Proline also plays a role in wound healing and tissue repair.

Nutritional Supplements: L-Proline is used as a dietary supplement to support joint health and promote collagen synthesis. It is often included in formulations targeting skin health, as collagen is a major component of the skin's structure. L-Proline supplements are also taken to support muscle growth and recovery.

Cosmetics: L-Proline is utilized in cosmetic products for its moisturizing and anti-aging properties. It helps to improve skin elasticity and reduce the appearance of wrinkles. L-Proline is commonly found in skincare creams, serums, and lotions.

Storage Conditions
Store in a cool, dry place.

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3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 229 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 226 of 229 companies. For more detailed information, please visit ECHA C&L website

Of the 2 notification(s) provided by 3 of 229 companies with hazard statement code(s):

H303+H333 (33.33%): May be harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]
H303 (33.33%): May be harmful if swallowed [Warning Acute toxicity, oral]
H315 (66.67%): Causes skin irritation [Warning Skin corrosion/irritation]
H316 (33.33%): Causes mild skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H333 (33.33%): May be harmful if inhaled [Warning Acute toxicity, inhalation]
H335 (66.67%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

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3.3 Methods of Manufacturing: From alpha-piperidone;; from cyclopentantone; from l-glutamic acid;

3.4 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.] L-Proline Preparation Products And Raw materials Raw materials

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3.5 Usage: amino acid, nutrient

4. Safety and Handling

4.1 Exposure Standards and Regulations: Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

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4.2 Octanol/Water Partition Coefficient: Log P = -2.54

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

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4.4 Formulations/Preparations: USP and FCC grades

4.5 Safety: Hazard Codes:?Xi,Xn
Risk Statements: 36/37/38-22
36/37/38:?Irritating to eyes, respiratory system and skin?
22:?Do not breathe dust??
Safety Statements: 24/25-36/37/39-26
24/25:?Avoid contact with skin and eyes?
36/37/39:?Wear suitable protective clothing, gloves and eye/face protection?
26:?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
WGK Germany: 3
RTECS: TW3584000
F: 3-10: Hygroscopic. Keep under argon.
HS Code: 29339990

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4.6 Specification: 1. First Aid Measures:
Ingestion: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately.
Inhalation: Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin: Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
2. Handling and Storage
Storage: Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling: Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with skin and eyes. Keep container tightly closed. Avoid ingestion and inhalation.

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4.7 Toxicity: LD50 orally in Rabbit: > 5110 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in D2O (PH 1.27)

13C NMR : in D2O (PH 7.26)

13C NMR : in D2O (PH 9.80)

IR : KBr disc

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

147-85-3Total: 119 Synthesis Route

70-26-8 71 Suppliers

147-85-3 620 Suppliers

74-79-3 667 Suppliers

147-85-3 620 Suppliers

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8. Precursor and Product

precursor:

98-79-3

372-75-8

70-26-8

58-82-2

56-86-0

108-95-2

609-36-9

74-79-3

344-25-2

product:

471-87-4

618-27-9

123-75-1

475-11-6

51-35-4

56-12-2

660-88-8

704-15-4

73-22-3

609-36-9

9. Computed Properties

Molecular Weight：115.13g/mol
Molecular Formula：C₅H₉NO₂
Compound Is Canonicalized：True
XLogP3-AA：115.063328530
Monoisotopic Mass：115.063328530
Complexity：103
Rotatable Bond Count：1
Hydrogen Bond Donor Count：2
Hydrogen Bond Acceptor Count：3
Topological Polar Surface Area：49.3
Heavy Atom Count：：8
Defined Atom Stereocenter Count：1
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBiMAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAAAAAAAHgAQCAAACCjBgAQACALAAgAIAACQCAAAAAAAAAAAAIGIAAACABIAgCAEQAAEEACQAACYEQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: 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.

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Merck: 14,7780

BRN: 80810

Chemical Properties: White crystalline powder

Chemical Properties: L-Proline, an amino acid, is odorless or has a slight, characteristic odor with a slightly sweet taste.

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: amino acid, nutrient

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: From α-piperidone; from cyclopentantone; from l-glutamic acid.

General Description: L-Proline is a non-essential amino acid. 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.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

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11. Toltal 570 Suppliers View more

Hebei Mojin Biotechnology Co.,Ltd

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Baoji Guokang Healthchem co.,ltd

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Wuhan Fortuna Chemical Co., Ltd.

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Tel: Update Time:2024/08/08

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Hangzhou Dingyan Chem Co.,Ltd

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Tel: Update Time:2024/11/15

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Wholesale price High purity 98.5% L-Proline EINECS 205-702-2 favorable price With stock

Tianjin Furun Tongda International Trade Co., LTD

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Tel: Update Time:2024/11/15

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12. Related Questions

: What is the role of L-Proline in protein synthesis and organic reactions? Description L-proline is a crucial amino acid utilized by the human body for protein synthesis. Encoded in the genetic code with specific codons, L-proline is unique as a secondary amine. It plays a ..; Why is L-Proline essential for maintaining youthful skin and repairing muscle damage?L-Proline is a crucial amino acid utilized as a protein component in living organisms. It plays a significant role in cartilage, aiding in the maintenance of youthful skin and the repair of muscle, co..; What are the applications of N-BOC-4-carbonyl-L-L-Proline methyl ester in drug synthesis?Application of N -BOC- 4 -carbonyl- L - L-Proline methyl ester in drug synthesisSynthesis of new Boc-protected cyclopropane modified L-Proline analogsA new member of the cyclopropane-modified L-Prolin..; What are the benefits of L-Proline?L-Proline is a cyclic amino acid and an important component of animal collagen. It is often accumulated in plants under various stress conditions such as drought, high temperature, low temperature, an..

13. Realated Product Infomation