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98-79-3

Basic Information
CAS No.: 98-79-3
Name: L-Pyroglutamic acid
Article Data: 64
Molecular Structure:
Molecular Structure of 98-79-3 (L-Pyroglutamic acid)
Formula: C5H7NO3
Molecular Weight: 129.115
Synonyms: Proline, 5-oxo-;Pyrrolidonecarboxylic acid;2-Pyrrolidinone-5-carboxylic acid;Proline, 5-oxo-, L-;(S)-5-Oxo-2-pyrrolidinecarboxylic acid;2-Pyrrolidone-5-Carboxylicacid;H-PYR-OH;pGlu-OH;L-Pyr-OH;L-Pyro Glutamic Acid;L-pyroglutamate;2-Oxopyrrolidine-5-carboxylic acid;Acido pidolico [INN-Spanish];5-Pyrrolidone-2-carboxylic acid;2-Benzothiazolesulfenic acid morpholide;L-5-Oxo-2-pyrrolidinecarboxylic acid;Pidolic acid [INN];L-Glutamic acid gamma-lactam;(2R)-5-oxopyrrolidine-2-carboxylate;35255-51-7;Acidum pidolicum [INN-Latin];L-Proline, 5-oxo-;CPD-589;2-Benzothiazolesulfenemorpholide;5-Carboxy-2-pyrrolidinone;Acide pidolique [INN-French];L-5-Pyrrolidone-2-carboxylic acid;(-)-2-Pyrrolidone-5-carboxylic acid;L-5-Carboxy-2-pyrrolidinone;(S)-(-)-2-Pyrrolidone-5-carboxylic acid;5-oxo-L-proline;2-L-Pyrrolidone-5-carboxylic acid;
EINECS: 202-700-3
Density: 1.38 g/cm3
Melting Point: 160-163 °C(lit.)
Boiling Point: 453.1 °C at 760 mmHg
Flash Point: 227.8 °C
Solubility: 10-15 g/100 mL (20 °C) in water
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 66.40000
LogP: -0.32160
Synthetic route
56-86-0

L-glutamic acid

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
With water for 16h; Heating;95%
In water for 16h; Heating;95%
With 1,1'-carbonyldiimidazole In chloroform at 55℃; for 3h; Solvent; Concentration;76.8%
53100-44-0

L-N-t-butoxycarbonylpyroglutamic acid

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
With silica gel In dichloromethane for 0.0166667h; Irradiation;91%
With tin(II) trifluoromethanesulfonate In dichloromethane at 20℃; for 2h;87%
91229-91-3

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature;90%
1676-73-9

L-glutamic acid γ-benzyl ester

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide at 40℃; for 20h;88.3%
317845-09-3

(5S)-2,2-bis(trifluoromethyl)-1-aza-3-oxabicyclo[3.3.0]octan-4,8-dione

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
With water In isopropyl alcohol at 20℃;87%
56-86-0

L-glutamic acid

A

149-87-1

Pyroglutamic acid

B

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
at 175℃; under 3750.38 Torr; for 5h; Temperature; Pressure; Autoclave; Large scale;A 15.9%
B 83%
13726-85-7

Boc-Gln-OH

76-05-1

trifluoroacetic acid

A

56-86-0

L-glutamic acid

B

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
at 20℃; for 0.25h;A 61%
B 18%
220280-79-5

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

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
With water for 12h; Hydrolysis; cyclization; Heating;45%
1676-73-9

L-glutamic acid γ-benzyl ester

A

100-52-7

benzaldehyde

B

65-85-0

benzoic acid

C

98-79-3

L-Pyroglutamic acid

D

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrachloropalladate(II) In water Product distribution; Ambient temperature; initial pH:6.8; variation of initial pH and temperature;A 37%
B 4%
C n/a
D 24%
107930-17-6

H-Glu(OChp)-OH

98-79-3

L-Pyroglutamic acid

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide at 40℃; for 20h;4.1%
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Specification

The IUPAC name of L-Pyroglutamic acid is (2S)-5-oxopyrrolidine-2-carboxylic acid. With the CAS registry number 98-79-3, it is also named as 2-Benzothiazolesulfenemorpholide. The product's categories are Heterocycles; Pyrrolidine Series; Chiral; Pyroglutamic Acid [Pyr, pGu]; Unusual Amino Acids; Amino Acids; Biochemistry; Biological-modified Amino Acids; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Amino Acids; Nutraceuticals, and the other registry numbers are 16891-48-8; 29222-42-2; 312618-42-1; 35255-51-7; 498-91-9; 6886-28-8; 87430-62-4. Besides, it is white to light yellow crystal powder, which should be stored in a cool, dry, well ventilated warehouse away from fire and heat source. And the packaging must be sealed and not damp. In addition, this chemical is stable, and incompatible with bases, acids, strong oxidizing agents.

Physical properties about  L-Pyroglutamic acid are: (1)ACD/LogP: -1.348; (2)ACD/LogD (pH 5.5): -3.38; (3)ACD/LogD (pH 7.4): -4.88; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.512 ; (12)Molar Refractivity: 28.033 cm3; (13)Molar Volume: 93.496 cm3; (14)Polarizability: 11.113 10-24cm3; (15)Surface Tension: 54.6319999694824 dyne/cm; (16)Density: 1.381 g/cm3; (17)Flash Point: 227.848 °C; (18)Enthalpy of Vaporization: 78.09 kJ/mol; (19)Boiling Point: 453.134 °C at 760 mmHg

Preparation and Uses of L-Pyroglutamic acid: Please heat 42 % Glutamic acid solution for 3 hours at 140 °C. And you will obtain the reaction liquid that is the main component of L-Pyroglutamic acid. After decompression and concentration, crystallization, washing, drying, you will get the product. The yield is 94 %. Furthermore, this chemical is used as intermediate of organic synthesis, food additives. It is also used in biochemical study, medicine, cosmetics and other industries. Additionally, it is used as resolving agent.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing, gloves and eye/face protection. Moreover, in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1;
(2)InChIKey=ODHCTXKNWHHXJC-VKHMYHEASA-N;
(3)Smiles[C@@H]1(NC(=O)CC1)C(=O)O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral > 1gm/kg (1000mg/kg)   United States Patent Document. Vol. #4882359,
rat LD50 subcutaneous > 2gm/kg (2000mg/kg)   United States Patent Document. Vol. #4882359,

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