D-Pyroglutamic acid supplier

Name
D-Pyroglutamic acid
EINECS 223-735-0
CAS No. 4042-36-8
Article Data14
CAS DataBase
Density 1.38 g/cm³
Solubility Soluble in water
Melting Point 155-162 °C
Formula C₅H₇NO₃
Boiling Point 453.1 °C at 760 mmHg
Molecular Weight 129.115
Flash Point 227.8 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms (2R)-5-oxopyrrolidine-2-carboxylic acid;D-5-Pyrrolidone-2-carboxylic acid;5-oxo-D-proline;CPD-656;H-D-Pyr-OH;(R)-(+)-2-pyrrolidone-5-carboxylic acid;D- pGlu-OH;
PSA 66.40000
LogP -0.32160

Synthetic route

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
With oxygen; sodium hydrogencarbonate; platinum In water for 4h; Ambient temperature;	95%

: 307304-62-7
tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
With water In 1,4-dioxane for 12h; Hydrolysis; cyclization; Heating;	45%

: 6893-26-1
D-Glutamic acid

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
With water for 63h; Heating;
In water for 72h; Heating;
With D-glutamate cyclase from mouse In methanol at 37℃; for 1h; pH=8; Kinetics; Enzymatic reaction;
With sodium hydroxide In ethanol; water at 20℃; for 48h;
With DL-dithiothreitol; D-glutamate cyclase; manganese(ll) chloride In aq. buffer at 37℃; for 1h; pH=8; Kinetics; Enzymatic reaction;

: 98-79-3
L-Pyroglutamic acid

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
In water at 140℃; Rate constant; pH 8.0;

dextrorotatory pyroglutamamide: dextrorotatory pyroglutamamide

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
With barium dihydroxide; water

inactive form: inactive form

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
With Quinine

: 68766-96-1
ethyl (R)-2-pyrrolidone-5-carboxylate

A: 64-17-5
ethanol

B: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics;

: 64700-65-8
methyl (2R)-pyroglutamate

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaBH4 / ethanol / 2 h / Ambient temperature 2: 95 percent / NaHCO3, O2 / Pt / H2O / 4 h / Ambient temperature View Scheme

: 149-87-1
Pyroglutamic acid

A: 98-79-3
L-Pyroglutamic acid

B: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
With Ν,Ν-dimethyldehydroabietylamine In chloroform-d1 at 27℃; Resolution of racemate;

: 64-17-5
ethanol

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 68766-96-1
ethyl (R)-2-pyrrolidone-5-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 20℃;	100%
With thionyl chloride at 80℃; for 1.5h;	94%
sulfuric acid Reflux;

: 540-88-5
acetic acid tert-butyl ester

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 205524-46-5
tert-butyl (R)-5-oxopyrrolidine-2-carboxylate

Conditions

Conditions	Yield
With perchloric acid In water	100%
With perchloric acid In water at 20℃; for 24h; Inert atmosphere;	100%

: (R)-4-(3,5-dimethylisoxazol-4-yl)-N1-(1-(methylsulfonyl)pyrrolidin-3-yl)benzene-1,2-diamine

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: (R)-N-(5-(3,5-dimethylisoxazol-4-yl)-2-(((R)-1-(methylsulfonyl)pyrrolidin-3-yl)amino)phenyl)-5-oxopyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h;	100%

: 98-59-9
p-toluenesulfonyl chloride

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 128899-31-0
<(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
Stage #1: D-pyrrolidone-5-carboxylic acid With thionyl chloride In methanol at 20℃; for 4h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 15h; Stage #3: p-toluenesulfonyl chloride With dmap; triethylamine In dichloromethane at 20℃; for 16h;	100%

: 67-56-1
methanol

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 64700-65-8
methyl (2R)-pyroglutamate

Conditions

Conditions	Yield
With thionyl chloride for 12h;	98%
With thionyl chloride 1.) 0 deg C, 30 min, 2.) room temp., 3 h;	95%
With sulfuric acid at 20℃; for 24h;	95%

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: amlodipine (R)-(+)-pyroglutamate

Conditions

Conditions	Yield
	95.1%

: 1-(2-tert-butylphenyl)piperazine dihydrochloride

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 1252657-17-2
(5R)-5-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}pyrrolidin-2-one

Conditions

Conditions	Yield
Stage #1: 1-(2-tert-butylphenyl)piperazine dihydrochloride; D-pyrrolidone-5-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 16h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate	94%

: C12H11Cl2N3O

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: (R,E)-N-(4-(6,7-dichloro-4-oxoquinazolin-3(4H)-yl)but-2-en-1-yl)-5-oxopyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	90%

: 55456-41-2
(S)-benzyl 2-amino-3-(4-methoxyphenyl)propanoate

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: (S)-benzyl 3-(4-methoxyphenyl)-2-((R)-5-oxopyrrolidine-2-carboxamido)propanoate

Conditions

Conditions	Yield
Stage #1: (S)-benzyl 2-amino-3-(4-methoxyphenyl)propanoate With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: D-pyrrolidone-5-carboxylic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;	89%

: C27H37N3O5

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: C27H34N4O5

Conditions

Conditions	Yield
Stage #1: C27H37N3O5 With trifluoroacetic acid In dichloromethane at 0 - 20℃; Stage #2: D-pyrrolidone-5-carboxylic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	89%

: tert-butyl (3R)-3-amino-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: tert-butyl (3R)-3-amino-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (2R)-5-oxopyrrolidine-2-carboxylate

Conditions

Conditions	Yield
In ethanol at 63℃;	89%
In ethanol at 63℃; Inert atmosphere;	89%
In ethanol at 63℃;	89%
In ethanol at 65℃;	19.2 g

: 20667-12-3
silver(l) oxide

: 98-79-3
L-Pyroglutamic acid

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: [Ag2(R-pyrrld)(S-pyrrld)]

Conditions

Conditions	Yield
In water to suspn. of Ag2O in water was added soln. of ligand in water, stirred for 2 h; filtered off, acetone vapor was diffused, collected, washed with Et2O, dried in vacuo; elem. anal.;	86.2%

...Expand

: C16H21F3N2O2S*C2HF3O2

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 1428535-89-0
thioacetic acid S-[(S)-6-[((R)-5-oxo-pyrrolidine-2-carbonyl)-amino]-6-(3-trifluoromethyl-phenylcarbamoyl)-hexyl] ester

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	84%

: 2-{(5-methoxy-1H-indole-3yl)-methylene}-N-pentylhydrazine carboxidamide

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: (x)C5H7NO3*C16H23N5O

Conditions

Conditions	Yield
In methanol at 20℃; for 1h;	84%

: C16H24N2O2S*C2HF3O2

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 1428535-79-8
thioacetic acid S-{(S)-6-[((R)-5-oxo-pyrrolidine-2-carbonyl)-amino]-6-m-tolylcarbamoyl-hexyl} ester

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	80%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;

: 540-36-3
para-difluorobenzene

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: C10H9F2NO

Conditions

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide; Eaton’s reagent at 50 - 65℃; for 27h; Temperature; Inert atmosphere;	78%

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 64700-65-8
methyl (2R)-pyroglutamate

Conditions

Conditions	Yield
With thionyl chloride In methanol at 20℃; Inert atmosphere;	75%

: 107-18-6
allyl alcohol

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: allyl (R)-5-oxopyrrolidine-2-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 23℃; for 3h; Inert atmosphere;	71%

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 322640-14-2
(-)-8-(4-phenylphenyl)menthol

: (1R,2S,5R)-2-(2-([1,1'-biphenyl]-4-yl)propan-2-yl)-5-methylcyclohexyl (R)-5-oxopyrrolidine-2-carboxylate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 23℃; for 24.5h; Inert atmosphere;	69%

: (1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-10-ol

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: (R)-5-((1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-10-hydroxy-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-3-carbonyl) pyrrolidin-2-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 14h;	58%

: 6859-99-0
3-hydroxypiperazine

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: (S)-3-hydroxypiperidine D-pyroglutamate

Conditions

Conditions	Yield
In ethanol for 1.5h; Time; Reflux; Large scale;	55%

: 100-46-9
benzylamine

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 178327-71-4
(R)-5-oxopyrrolidine-2-carboxylic acid benzylamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 0 - 20℃; for 3h;	48%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 3h; Cooling with ice;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 3h; Cooling with ice;

: 905585-65-1
(S)-3-aminomethyl-N6-(5-cyclopropyl-1H-pyrazol-3-yl)-5-fluoro-N2-[1-(4-fluorophenyl)ethyl]pyridine-2,6-diamine

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 905586-73-4
(R)-N-((6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-((S)-1-(4-fluorophenyl)ethylamino)pyridin-3-yl)methyl)-5-oxo-pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: (S)-3-aminomethyl-N6-(5-cyclopropyl-1H-pyrazol-3-yl)-5-fluoro-N2-[1-(4-fluorophenyl)ethyl]pyridine-2,6-diamine; D-pyrrolidone-5-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; dichloromethane	43%

Yield

Stage #1: (S)-3-aminomethyl-N6-(5-cyclopropyl-1H-pyrazol-3-yl)-5-fluoro-N2-[1-(4-fluorophenyl)ethyl]pyridine-2,6-diamine; D-pyrrolidone-5-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 1h;
Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; dichloromethane

43%

: (S)-N-cinnamoylserinecyclohexylamide

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: (S)-N-cinnamoylserine{3-(R)-pyroglutamoyl}cyclohexylamide

Conditions

Conditions	Yield
With oxalyl dichloride; triethylamine In N,N-dimethyl-formamide	25%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 128899-30-9, 100548-49-0, 106191-02-0
(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

Conditions

Conditions	Yield
Stage #1: D-pyrrolidone-5-carboxylic acid With thionyl chloride In methanol at 0 - 20℃; for 1h; Stage #2: With sodium tetrahydroborate In ethanol at 0 - 20℃; for 16h; Stage #3: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;	24%

: [3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine hydrochloride

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-5-oxo-D-prolineamide

Conditions

Conditions	Yield
Stage #1: D-pyrrolidone-5-carboxylic acid With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In tetrahydrofuran at 0℃; for 2h; Stage #2: [3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine hydrochloride With 4-methyl-morpholine In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 20℃; for 15h; Stage #3: With sodium methylate In methanol at 20℃; for 1h;	8%

: 7-fluoronaphtho[2,1-d]thiazol-2-amine

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: (R)-N-(7-fluoronaphtho[2,1-d]thiazol-2-yl)-5-oxopyrrolidine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: D-pyrrolidone-5-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: 7-fluoronaphtho[2,1-d]thiazol-2-amine In N,N-dimethyl-formamide at 60℃; for 16h;	5%

D-Pyroglutamic acid Specification

The IUPAC name of D-Pyroglutamic acid is (2S)-5-oxopyrrolidine-2-carboxylic acid . With the CAS registry number 4042-36-8, it is also named as 5-Oxo-D-proline ; D-5-Pyrrolidone-2-carboxylic acid ; (R)-(+)-2-Pyrrolidone-5-carboxylic acid . The product's categories are amino acids and derivatives, heterocycles, pharmacetical, chiral, biochemistry, optical resolution, synthetic organic chemistry and chiral reagents.

The D-Pyroglutamic acid is white to light yellow crystal powder which should be stores at the temperature of 0-5°C. It serves as a building block in the synthesis of diphthamide. It is used as pharmaceutical intermediates. This product is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.91 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -3 ; (4)ACD/LogD (pH 7.4): -5 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 1 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 4 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 0 ; (12)Index of Refraction: 1.551 ; (13)Molar Refractivity: 28.251 cm³ ; (14)Molar Volume: 88.526 cm³ ; (15)Polarizability: 11.2×10^-24 cm³ ; (16)Surface Tension: 68.09 dyne/cm ; (17)Enthalpy of Vaporization: 55.943 kJ/mol ; (18)Vapour Pressure: 0.002 mmHg at 25°C ; (19)Rotatable Bond Count: 1 ; (20)Tautomer Count: 3 ; (21)Exact Mass: 129.042593 ; (22)MonoIsotopic Mass: 129.042593 ; (23)Topological Polar Surface Area: 66.4 ; (24)Heavy Atom Count: 9.

People can use the following data to convert to the molecule structure. SMILES: O=C1N(C(=O)O)CCC1; InChI: InChI=1/C5H7NO3/c7-4-2-1-3-6(4)5(8)9/h1-3H2,(H,8,9); InChIKey: DQAKJEWZWDQURW-UHFFFAOYAE. D-Pyroglutamic acid has many suppliers, such as AmiA Biochemical Industrial Co., Ltd., Changzhou Banghe Aminophenol Technology Co., Ltd., Chengdu Unibiochem Co., Ltd. and Hitrox Bioscience Co., Ltd..

Product Name

D-Pyroglutamic acid

Synthetic route

D-Pyroglutamic acid Specification

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