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Basic Information

Molecular Structure:
CAS No.:	98-79-3
Name:	L-Pyroglutamic acid
Article Data:	64
Cas Database

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:	Xi
Risk Codes:	36/37/38
Safety:	26-36-37/39
PSA:	66.40000
LogP:	-0.32160

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Synthetic route

: 56-86-0
L-glutamic acid

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L-Pyroglutamic acid

Conditions

Conditions	Yield
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%

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L-N-t-butoxycarbonylpyroglutamic acid

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L-Pyroglutamic acid

Conditions

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

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

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L-Pyroglutamic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature;	90%

: 1676-73-9
L-glutamic acid γ-benzyl ester

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L-Pyroglutamic acid

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 40℃; for 20h;	88.3%

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

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L-Pyroglutamic acid

Conditions

Conditions	Yield
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

Conditions	Yield
at 175℃; under 3750.38 Torr; for 5h; Temperature; Pressure; Autoclave; Large scale;	A 15.9% B 83%

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Boc-Gln-OH

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trifluoroacetic acid

A: 56-86-0
L-glutamic acid

B: 98-79-3
L-Pyroglutamic acid

Conditions

Conditions	Yield
at 20℃; for 0.25h;	A 61% B 18%

...Expand

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

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L-Pyroglutamic acid

Conditions

Conditions	Yield
With water for 12h; Hydrolysis; cyclization; Heating;	45%

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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

Conditions	Yield
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%

...Expand

: 107930-17-6
H-Glu(OChp)-OH

: 98-79-3
L-Pyroglutamic acid

Conditions

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

Raw Materials

70-18-8

Downstream Products

147-85-3

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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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