L-Proline supplier | CasNO.147-85-3

Name
L-Proline
EINECS 205-702-2
CAS No. 147-85-3
Article Data264
CAS DataBase
Density 1.186 g/cm³
Solubility soluble
Melting Point 228 °C (dec.)(lit.)
Formula C₅H₉NO₂
Boiling Point 252.2 °C at 760 mmHg
Molecular Weight 115.132
Flash Point 106.3 °C
Transport Information
Appearance White crystalline powder
Safety 24/25-36/37/39-26
Risk Codes 36/37/38-22
Molecular Structure
Hazard Symbols Xn,Xi
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;
PSA 49.33000
LogP 0.15180

Synthetic route

: 110637-44-0
(2S)-N-allyloxycarbonyl-L-proline

: 147-85-3
L-proline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
	A n/a B 99%

: 86050-92-2
L-1-(chlorocarbonyl)proline ethyl ester

: 147-85-3
L-proline

Conditions

Conditions	Yield
With hydrogenchloride at 25 - 75℃;	98%

: 91237-84-2
N-BOC-proline tert-butyl ester

: 147-85-3
L-proline

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 2h;	98%
With trifluoroacetic acid	82%

: 85665-59-4
(S)-methyl 1-(chlorocarbonyl)pyrrolidine-2-carboxylate

: 147-85-3
L-proline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride; water at 100℃; for 24h;	A n/a B n/a C 95%

...Expand

: 110637-44-0
(2S)-N-allyloxycarbonyl-L-proline

A: 147-85-3
L-proline

B: 610299-77-9
(S)-1-allylproline

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: C5H9NO2*H3N*ClH

: 147-85-3
L-proline

Conditions

Conditions	Yield
With ruthenium nanoparticles dispersed in a polyvinylpyrrolidone matrix; amberlyst A-21 In methanol; dichloromethane	92%

: 42429-27-6
L-prolinamide hydrochloride

: 147-85-3
L-proline

Conditions

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

: cinnamyl-L-prolinate

: 147-85-3
L-proline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
	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

Conditions	Yield
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

Conditions	Yield
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

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

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

: 147-85-3
L-proline

Conditions

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

: L-proline methanesulfonic acid salt

: 147-85-3
L-proline

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 0.5h; Solvent;	70%

: 70-26-8
L-ornithine

: 147-85-3
L-proline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride for 2h; Heating;	100%
With thionyl chloride Heating;	100%
With sulfuryl dichloride	100%

: 98-88-4
benzoyl chloride

: 147-85-3
L-proline

: 5874-58-8
N-(benzoyl)-L-proline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium carbonate Inert atmosphere;	100%
With water; sodium hydroxide at 70℃; for 2h;	99%
In sodium hydroxide	98.3%

: 147-85-3
L-proline

: 23356-96-9
(S)-1-Pyrrolidin-2-yl-methanol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium carbonate In methanol	100%
With potassium carbonate at 0 - 20℃;	100%
With potassium carbonate at 0 - 20℃; for 7.5h; Inert atmosphere;	100%

...Expand

: 541-41-3
chloroformic acid ethyl ester

: 147-85-3
L-proline

: 5700-74-3
(S)-N-(ethoxycarbonyl)proline

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide for 0.5h;	100%
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃;	0.77 g

: 147-85-3
L-proline

: 567-35-1, 567-36-2, 4298-05-9, 4298-06-0, 4298-08-2, 14916-76-8, 62182-84-7, 104069-26-3, 118492-86-7, 119677-21-3
(2S,3R)-3-hydroxyproline

Conditions

Conditions	Yield
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

Conditions	Yield
In methanol at 0 - 20℃; for 3h; Inert atmosphere;	100%
In methanol	97%
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

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 5h; Heating;	100%
With sodium hydrogencarbonate In ethanol; water Heating;	94%
With triethylamine In dimethyl sulfoxide	80.3%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With n-butyllithium	A 100% B n/a

...Expand

: 147-85-3
L-proline

: 2133-40-6
L-proline methyl ester monohydrochloride

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In tetrachloromethane for 24h; Reflux;	100%
In cyclohexane for 4h; Solvent; Fischer-Speier Esterification; Reflux; Dean-Stark;	100%

...Expand

L-Proline History

Hermann Emil Fischer discovered proline between 1899 and 1908.

L-Proline 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: Irritant Xi, Harmful 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

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.

Product Name

L-Proline

Synthetic route

L-Proline History

L-Proline Specification

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