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D-Pyroglutamic acid

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Name

D-Pyroglutamic acid

EINECS 223-735-0
CAS No. 4042-36-8 Density 1.38 g/cm3
PSA 66.40000 LogP -0.32160
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 N/A Appearance white to light yellow crystal powder
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 4042-36-8 (D-Pyroglutamic acid) Hazard Symbols IrritantXi
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;

Article Data 14

D-Pyroglutamic acid Synthetic route

66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In water at 140℃; Rate constant; pH 8.0;
dextrorotatory pyroglutamamide

dextrorotatory pyroglutamamide

4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With barium dihydroxide; water
inactive form

inactive form

4042-36-8

D-pyrrolidone-5-carboxylic acid

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

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..

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