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147-85-3

Basic Information
CAS No.: 147-85-3
Name: L-Proline
Molecular Structure:
Molecular Structure of 147-85-3 (L-Proline)
Formula: C5H9NO2
Molecular Weight: 115.13
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:
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%
71989-31-6

Fmoc-Pro-OH

A

4425-82-5

9-methylene-fluorene

B

147-85-3

L-proline

Conditions
ConditionsYield
With dimethyl sulfoxide at 120℃; for 0.333333h;A n/a
B 96%
1319113-54-6

(3RS,6S)-3-[di(methoxycarbonyl)methyl]-1,6-trimethylene-2,5-piperazinedione

A

71855-54-4

D-aspartic acid hydrochloride

B

17585-59-0

L-aspartic acid hydrochloride

C

147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride; water at 100℃; for 24h;A n/a
B n/a
C 95%
110637-44-0

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

A

147-85-3

L-proline

B

610299-77-9

(S)-1-allylproline

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20 - 40℃;A 93%
B n/a
7531-52-4

L-prolinamide

147-85-3

L-proline

Conditions
ConditionsYield
Stage #1: L-prolinamide With hydrogenchloride for 10h; Heating;
Stage #2: With methyloxirane In ethanol at 20℃; for 5h;
92%
71989-31-6

Fmoc-Pro-OH

147-85-3

L-proline

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 50℃; for 3h;92%

C5H9NO2*H3N*ClH

147-85-3

L-proline

Conditions
ConditionsYield
With ruthenium nanoparticles dispersed in a polyvinylpyrrolidone matrix; amberlyst A-21 In methanol; dichloromethane92%
42429-27-6

L-prolinamide hydrochloride

147-85-3

L-proline

Conditions
ConditionsYield
With Amberlyst 15; water at 100℃; for 72h;90%

cinnamyl-L-prolinate

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 0.666667h;86%
610299-77-9

(S)-1-allylproline

147-85-3

L-proline

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 40℃;86%
108-95-2

phenol

147-85-3

L-proline

Conditions
ConditionsYield
86%
1319113-56-8

(3R,6S,1'RS)-3-(methoxycarbonylcyanomethyl)-1,6-trimethylene-2,5-piperazinedione

A

71855-54-4

D-aspartic acid hydrochloride

B

147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride; water at 100℃; for 24h;A 84%
B 82%

(S)-tetrahydro-3'H-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,1'-pyrrolo[1,2-c][1,3,2]oxazaborol]-3'-one

147-85-3

L-proline

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 7h;82%
205875-07-6

(3R,8aS)-hexahydro-3-(prop-2-enyl)pyrrolo[1,2-a]pyrazine-1,4-dione

A

54594-06-8

D-allylglycine

B

147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride at 90℃; for 10h;A 80%
B 62%

L-proline (+)-10-camphorsulfonic acid salt

147-85-3

L-proline

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 0.5h;78%

L-proline methanesulfonic acid salt

147-85-3

L-proline

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 0.5h; Solvent;70%
70-26-8

L-ornithine

147-85-3

L-proline

Conditions
ConditionsYield
platinum(IV) oxide; Pt/titania In water for 41h; Irradiation; pH 9.8;43%
platinum(IV) oxide; Pt/titania In water for 41h; Product distribution; Irradiation; pH 9.8; other amino acids and derivatives; other catalyst and rection time;
With Pseudomonas putida N-methyl-L-amino acid dehydrogenase; T. viride L-lysine oxidase; Tris buffer; flavin adenine dinucleotide; catalase In various solvent(s) at 30℃; for 2h; pH=8.0;
With benzenesulfonamide; ornithine cyclodeaminase; NAD In various solvent(s) at 30℃; pH=8.0;
With NAD; dehydrogenase from Candida boidinii; pyrroline-5-carboxylate reductase from Halomonas elongata; transaminase from Halomonas elongata; 2-oxo-propionic acid In aq. buffer at 37℃; pH=10; Reagent/catalyst; Enzymatic reaction;

(S)-proline (S)-1,1'-bi-2-naphthol 1:2 complex

18531-99-2

(S)-[1,1']-binaphthalenyl-2,2'-diol

B

147-85-3

L-proline

Conditions
ConditionsYield
In water; ethyl acetate at 20℃; for 2h;A 42%
B 0.257 g
67-56-1

methanol

147-85-3

L-proline

2577-48-2

methyl (2S)-pyrrolidine carboxylate

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;100%
With thionyl chloride Heating;100%
With sulfuryl dichloride100%
98-88-4

benzoyl chloride

147-85-3

L-proline

5874-58-8

N-(benzoyl)-L-proline

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 0 - 20℃;100%
With sodium hydroxide In water at 0℃; for 2h;89%
With potassium carbonate In tetrahydrofuran at 60℃;85%
501-53-1

benzyl chloroformate

147-85-3

L-proline

1148-11-4

N-Benzyloxycarbonyl-L-proline

Conditions
ConditionsYield
With sodium hydroxide In water for 13.5h; Ambient temperature;100%
With sodium carbonate at 0 - 20℃; for 3h;100%
With sodium hydroxide at 0℃; for 0.166667h;97%
98-59-9

p-toluenesulfonyl chloride

147-85-3

L-proline

51077-01-1, 110771-95-4

L-N-tosyl-proline

Conditions
ConditionsYield
With sodium carbonate Inert atmosphere;100%
With water; sodium hydroxide at 70℃; for 2h;99%
In sodium hydroxide98.3%
147-85-3

L-proline

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

Conditions
ConditionsYield
Stage #1: L-proline With lithium aluminium tetrahydride In tetrahydrofuran for 1.25h; Heating / reflux;
Stage #2: With potassium hydroxide In tetrahydrofuran; water for 1.25h; Heating / reflux;
100%
Stage #1: L-proline With lithium aluminium tetrahydride In tetrahydrofuran Inert atmosphere; Cooling with ice; Reflux;
Stage #2: With potassium hydroxide In tetrahydrofuran at 20℃; Reflux;
99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 72.5h; Reflux;99%
67-56-1

methanol

147-85-3

L-proline

2133-40-6

L-proline methyl ester monohydrochloride

Conditions
ConditionsYield
With thionyl chloride for 1.5h; Heating;100%
With hydrogenchloride for 4h; Ambient temperature;100%
With thionyl chloride for 1.5h; Heating;100%
118-48-9

isatoic anhydride

147-85-3

L-proline

24919-40-2, 60269-66-1, 18877-34-4

(S)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 160℃; for 4h;100%
In dimethyl sulfoxide at 180℃; Condensation;96%
In dimethyl sulfoxide at 100℃; for 4h;95%
64-17-5

ethanol

147-85-3

L-proline

33305-75-8

L-proline ethyl ester monohydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 1h; Heating;100%
With thionyl chloride for 12h; Reflux; Green chemistry;99%
Stage #1: L-proline With thionyl chloride In ethanol for 6h; Heating;
Stage #2: ethanol Further stages.;
98%
24424-99-5

di-tert-butyl dicarbonate

147-85-3

L-proline

15761-39-4

1-(tert-butoxycarbonyl)-L-proline

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 19h; Cooling with ice;100%
With amberlyst-15 In ethanol at 20℃; for 0.0833333h; chemoselective reaction;100%
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 16h;100%
67-56-1

methanol

541-41-3

chloroformic acid ethyl ester

147-85-3

L-proline

77581-28-3, 93423-88-2

(S)-proline-N-ethyl carbamate methyl ester

Conditions
ConditionsYield
With potassium carbonate In methanol100%
With potassium carbonate at 0 - 20℃;100%
With potassium carbonate at 0 - 20℃; for 7.5h; Inert atmosphere;100%
541-41-3

chloroformic acid ethyl ester

147-85-3

L-proline

5700-74-3

(S)-N-(ethoxycarbonyl)proline

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran at 0℃; for 2h;100%
Stage #1: chloroformic acid ethyl ester; L-proline With sodium hydroxide; water at 0 - 20℃; pH=9 - 10;
Stage #2: With hydrogenchloride; water at 0℃; pH=1;
100%
With sodium hydrogencarbonate In water at 25℃; for 12h;96%
98-09-9

benzenesulfonyl chloride

147-85-3

L-proline

88425-46-1

N-benzenesulfonyl-L-proline

Conditions
ConditionsYield
With sodium carbonate In water for 5h;100%
With sodium carbonate In water for 4h;100%
With sodium carbonate In water at -5 - 20℃; for 4h; Inert atmosphere;100%
933-88-0

ortho-toluoyl chloride

147-85-3

L-proline

N-(2-methylbenzoyl)-L-proline

Conditions
ConditionsYield
With sodium hydroxide for 0.5h;100%
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃;0.77 g
Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; cis-3-proline hydroxylase type II; sodium L-ascorbate at 37℃; for 16h; stereospecific reaction;100%
With iron(II) sulfate; α-ketoglutaric acid disodium salt In culture medium at 28℃; for 72h; Enzymatic reaction; regioselective reaction;61%
With 4-morpholineethanesulfonic acid; α-ketoglutaric acid; bovine serum albumin; proline 3-hydroxylase; iron(II) sulfate In water pH=6.0; Oxidation; hydroxylation;
With hydrogenchloride; α-ketoglutaric acid; ammonium iron (II) sulfate; L-proline cis-3-hydroxylase type I; sodium L-ascorbate In aq. buffer at 21℃; for 14h; pH=6.5; Enzymatic reaction;> 95 %Chromat.
With ferrous(II) sulfate heptahydrate; α-ketoglutaric acid disodium salt; ascorbic acid In aq. phosphate buffer at 37℃; for 16h; pH=7.5; Enzymatic reaction;530 mg
2052-49-5

tetra(n-butyl)ammonium hydroxide

147-85-3

L-proline

proline, tetrabutylammonium carboxylate salt

Conditions
ConditionsYield
In methanol at 0 - 20℃; for 3h; Inert atmosphere;100%
In methanol97%
In water at 20℃; for 2h;95%
1493-27-2

ortho-nitrofluorobenzene

147-85-3

L-proline

31981-54-1

(S)-N-(2-nitrophenyl)proline

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water for 5h; Heating;100%
With sodium hydrogencarbonate In ethanol; water Heating;94%
With triethylamine In dimethyl sulfoxide80.3%
With sodium hydrogencarbonate In ethanol; water at 100℃;
2937-50-0

Allyl chloroformate

147-85-3

L-proline

110637-44-0

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

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether at 20℃; for 16h;100%
With hydrogenchloride; sodium hydroxide In tetrahydrofuran; water
71447-81-9

N-benzyloxycarbonyl-(2S)-aminobutyric acid succinimide ester

147-85-3

L-proline

185212-64-0

N-benzyloxycarbonyl-(2S)-aminobutyryl-L-proline

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water at 20℃;100%
776330-84-8

3-benzo[b]thiophen-2-yl-3-tert-butoxycarbonylamino-propionic acid

147-85-3

L-proline

776330-85-9

[1-benzo[b]thiophen-2-yl-3-(2-S-carbamoyl-pyrrolidin-1-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In DMF (N,N-dimethyl-formamide) at 20℃; for 2.5h;100%
869882-73-5

C22H24N2O5

147-85-3

L-proline

C27H33N3O7

Conditions
ConditionsYield
In dichloromethane at 20℃; for 18h;100%
2320-32-3

6-methyl-6-phenylfulvene

147-85-3

L-proline

A

salt of L-proline+6-methyyl-6-phenylfulvene

salt of L-proline+6-methyyl-6-phenylfulvene

B

α-phenethylcyclopentadiene

Conditions
ConditionsYield
With n-butyllithiumA 100%
B n/a
147-85-3

L-proline

2133-40-6

L-proline methyl ester monohydrochloride

Conditions
ConditionsYield
With thionyl chloride In methanol at 20℃;100%
With sulfuryl dichloride; trimethyl orthoformate In methanol
With sulfuryl dichloride; trimethyl orthoformate In methanol
With sulfuryl dichloride; trimethyl orthoformate In methanol
14873-53-1

di(μ-chloro)bis[1-(phenylazo)phenyl-C(2)N]dipalladium(II)

147-85-3

L-proline

Pd(C6H4NNC6H5)(NHC4H7CO2)

Conditions
ConditionsYield
With NaOMe In methanol N2-atmosphere; dropwise addn. of 1 equiv. NaOMe to aminoacid, gentle heating to dissoln., addn. of stoich. amt. Pd-complex, stirring for 15 h; solvent removal (vac.), dissoln. in CH2Cl2, centrifugation, solvent removal (vac.), repeated recrystn. (CH2Cl2/hexane); elem. anal.;100%
504-02-9

1,3-cylohexanedione

147-85-3

L-proline

1033193-52-0

1-(3-oxocyclohex-1-enyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
In benzene for 5h; Reflux;100%
104-15-4

toluene-4-sulfonic acid

147-85-3

L-proline

100-51-6

benzyl alcohol

32302-87-7

L‑proline benzyl ester p‑toluenesulfonate

Conditions
ConditionsYield
In tetrachloromethane for 24h; Reflux;100%
In cyclohexane for 4h; Solvent; Fischer-Speier Esterification; Reflux; Dean-Stark;100%
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    147-85-3

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    High purity L(-)-Proline 98% CAS:147-85-3

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    L-Proline 147-85-3

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    L- proline

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  • L-Proline CAS NO.147-85-3

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    L-Proline CAS NO.147-85-3

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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.