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147-85-3

Basic Information
CAS No.: 147-85-3
Name: L-Proline
Article Data: 264
Cas Database
Molecular Structure:
Molecular Structure of 147-85-3 (L-Proline)
Formula: C5H9NO2
Molecular Weight: 115.132
Synonyms: L-Prolin;(S)-Pyrrolidine-2-carboxylic acid;L-Pyrrolidine-2-carboxylic acid;(-)-Proline (S)-2-Carboxypyrrolidine;CCCu;2-Pyrralidinecarboxylic acid, (S)-;2-Pyrrolidinecarboxylic acid, (S)-;(-)-2-Pyrrolidinecarboxylic acid;L-(-)-Proline;PRO;(2S)-2,3,4,5-tetrahydropyrrole-2-carboxylate;(S)-Proline;(-)-(S)-Proline;H-Pro-OH~(S)-Pyrrolidine-2-carboxylic acid;
EINECS: 205-702-2
Density: 1.186 g/cm3
Melting Point: 228 °C (dec.)(lit.)
Boiling Point: 252.2 °C at 760 mmHg
Flash Point: 106.3 °C
Solubility: soluble
Appearance: White crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 36/37/38-22
Safety: 24/25-36/37/39-26
Transport Information: N/A
PSA: 49.33000
LogP: 0.15180
Synthetic route
110637-44-0

(2S)-N-allyloxycarbonyl-L-proline

147-85-3

L-proline

Conditions
ConditionsYield
With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile for 0.25h; Ambient temperature;100%

(S)-Pyrrolidine-2-carboxylic acid 3-methyl-but-2-enyl ester

147-85-3

L-proline

Conditions
ConditionsYield
With diethylamine; Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) In water; acetonitrile for 0.75h;100%
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

147-85-3

L-proline

Conditions
ConditionsYield
With water at 170℃; for 0.05h; Microwave irradiation;100%
With tin(IV) chloride In ethyl acetate for 0.583333h; Ambient temperature;98%
With tetradecyl(trihexyl)phosphonium bistriflamide; trifluoroacetic acid at 130℃; for 0.166667h; Ionic liquid;96%
1148-11-4

N-Benzyloxycarbonyl-L-proline

147-85-3

L-proline

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 80℃; for 0.0833333h; Microwave irradiation;100%
With hydrogen; hydroxyapatite-bound Pd In methanol at 40℃; for 1h;99%
With hydrogen; palladium on activated charcoal In ethyl acetate at 80℃; under 2585.81 Torr; for 0.0833333h; microwave irradiation;99%
439912-48-8

Poc-Pro-OH

147-85-3

L-proline

Conditions
ConditionsYield
With resin bound tetrathiomolybdate In methanol at 28℃; for 1.5h; ultrasonic bath;100%
344-25-2

D-Prolin

147-85-3

L-proline

Conditions
ConditionsYield
With porcine kidney D-amino acid oxidase (EC 1.4.3.3.); sodium cyanoborohydride; flavin adenine dinucleotide In phosphate buffer at 37℃;99%
552-38-5

lithium salicylate

A

Lithium Salicylate Proline

B

147-85-3

L-proline

Conditions
ConditionsYield
A n/a
B 99%
86050-92-2

L-1-(chlorocarbonyl)proline ethyl ester

147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride at 25 - 75℃;98%
91237-84-2

N-BOC-proline tert-butyl ester

147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 2h;98%
With trifluoroacetic acid82%
85665-59-4

(S)-methyl 1-(chlorocarbonyl)pyrrolidine-2-carboxylate

147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride at 25 - 75℃;97%
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History

Hermann Emil Fischer discovered proline between 1899 and 1908.

Specification

1. Introduction of L-Proline

L-Proline, with the chemical name of 2-Pyrrolidinecarboxylic acid, is one kind of white crystalline powder. For being soluble in the water, L-Proline is incompatible with strong oxidizing agents, and it will belong to the Product Categories which include Food & Feed ADDITIVES; Amino Acid Derivatives; Proline [Pro, P]; Amino Acids; Amino Acids and Derivatives; alpha-Amino Acids; Biochemistry; Nutritional Supplements; L-Amino Acids; Amino Acids.

2. Properties of L-Proline

L-Proline has the following properties datas: (1)Index of Refraction: 1.487; (2)Molar Refractivity: 27.9 cm3; (3)Molar Volume: 96.9 cm3; (4)Polarizability: 11.06×10-24 cm3; (5)Surface Tension: 43.4 dyne/cm; (6)Density: 1.186 g/cm3; (7)Flash Point: 106.3 °C; (8)Enthalpy of Vaporization: 53.9 kJ/mol; (9)Melting Point: 228 °C (dec.)(lit.); (10)Boiling Point: 252.2 °C at 760 mmHg; (11)Vapour Pressure: 0.00615 mmHg at 25°C.

3. Structure Descriptors of L-Proline

You could convert the following datas into the molecular structure:
(1)InChI: InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
(2)InChIKey: InChIKey=ONIBWKKTOPOVIA-BYPYZUCNSA-N
(3)Smiles: C([C@@H]1CCCN1)(O)=O

4. Safety Information of L-Proline

Hazard Codes: IrritantXi,HarmfulXn
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

And following are some specific cases and their according 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.

5. Usage of L-Proline

L-Proline can be used as nutritional supplements, flavor agent, and aroma.It can also be used as pharmaceutical raw materials and food additives. It is one of the important amino acids of human proteins. It is also an important raw material for amino acid infusion. L-proline has been widely used in food and pharmaceutical industry . It is an osmoprotectant and therefore is used in many pharmaceutical, biotechnological applications.

6. Handling and Storage of L-Proline

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.