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Cas Database |
| Name |
Ethyl L-pyroglutamate |
EINECS | 230-480-9 |
| CAS No. | 7149-65-7 | Density | 1.161 g/cm3 |
| PSA | 55.40000 | LogP | 0.15690 |
| Solubility | N/A | Melting Point |
47-51 ºC |
| Formula | C7H11 N O3 | Boiling Point | 176 ºC (12 mmHg) |
| Molecular Weight | 157.169 | Flash Point | 142.9 °C |
| Transport Information | N/A | Appearance | Colorless or yellowish oily liquid |
| Safety | S26;S37/39 | Risk Codes | R36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
|
| Synonyms |
Proline,5-oxo-, ethyl ester, L- (7CI,8CI); (S)-(+)-Ethyl 2-pyrrolidone-5-carboxylate;Ethyl (2S)-5-oxopyrrolidine-2-carboxylate; Ethyl (S)-pyroglutamate; EthylL-2-oxo-5-pyrrolidinecarboxylate; Ethyl L-2-pyrrolidone-5-carboxylate; EthylL-pyroglutamate; Ethyl pyroglutamate; L-2-Ethoxycarbonyl-5-pyrrolidone;L-Pyroglutamic acid ethyl ester; NSC 166529; NSC 72279; Pyroglutamic acid ethylester |
Article Data | 51 |
Ethyl L-pyroglutamate Synthetic route
- 64-17-5
ethanol
- 14842-41-2
(S,S)-1,7-diazatricyclo[7.3.0.07,11]dodecane-2,6,8,12-tetrone
- 7149-65-7
ethyl (S)-pyroglutamate
| Conditions | Yield |
|---|---|
| With potassium cyanide for 4h; | 100% |
| Conditions | Yield |
|---|---|
| With thionyl chloride at 0 - 20℃; | 99% |
| With thionyl chloride at 0℃; for 15h; | 99% |
| With thionyl chloride at -5 - 20℃; for 10h; | 98% |
| Conditions | Yield |
|---|---|
| With thionyl chloride Heating; | 95% |
| With thionyl chloride 1.) r. t., 1 h, 2.) reflux, 0.5 h; | 87% |
| With thionyl chloride 1) room temperature, 1 h; 2) reflux, 0.5 h; | 87% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In dichloromethane at 0 - 20℃; for 6h; | 92% |
| With N-ethyl-N,N-diisopropylamine In acetonitrile at 10 - 20℃; for 72h; |
| Conditions | Yield |
|---|---|
| With thionyl chloride In ethanol 1) 0 deg C; 2) 1 h, room temp., then 0.5 h reflux; | 84% |
| With thionyl chloride In ethanol; water | |
| Multi-step reaction with 2 steps 1: 0.83 h / 220 - 290 °C / Autoclave; Large scale 2: toluene-4-sulfonic acid / methanol / -5 - 45 °C View Scheme |
| Conditions | Yield |
|---|---|
| In dichloromethane for 0.0833333h; Heating; | 81% |
- 16450-41-2
L-glutamic acid diethyl ester
- 7149-65-7
ethyl (S)-pyroglutamate
| Conditions | Yield |
|---|---|
| at 150℃; under 15.0015 Torr; Inert atmosphere; |
- 24424-99-5
di-tert-butyl dicarbonate
- 7149-65-7
ethyl (S)-pyroglutamate
- 144978-35-8, 144978-12-1
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
| Conditions | Yield |
|---|---|
| With dmap In acetonitrile at 20℃; | 100% |
| With dmap In dichloromethane at 20℃; for 6h; | 100% |
| With dmap In acetonitrile at 20℃; for 3h; | 98% |
- 902137-35-3
2-bromobenzaldehyde O-(phenylmethyl)oxime
- 7149-65-7
ethyl (S)-pyroglutamate
- 902137-36-4
(S)-1-[2-(Benzyloxyimino-methyl)-phenyl]-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
| Conditions | Yield |
|---|---|
| With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; | 99% |
- 902137-35-3
2-bromobenzaldehyde O-(phenylmethyl)oxime
- 7149-65-7
ethyl (S)-pyroglutamate
- 1032651-69-6
(S)-5-oxo-1-[2-[(E)-(phenylmethoxyimino)methyl]phenyl]proline ethyl ester
| Conditions | Yield |
|---|---|
| With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 8h; | 99% |
Ethyl L-pyroglutamate Chemical Properties
Molecular Formula: C7H11NO3
Molar mass: 157.178 g/mol
EINECS: 230-480-9
Density: 1.161 g/cm3
Flash Point: 142.9 °C
Index of Refraction: 1.466
Boiling Point: 312.7 °C at 760 mmHg
Vapour Pressure: 0.000519 mmHg at 25°C
Melting point: 54-56 °C
Storage temp: 0-6°C
Appearance: White to cream low melting solid
Product categories: pharmacetical;Pyroglutamic acid [Pyr, pGu];Chiral and Miscellaneous Reagents;Heterocycles
Structure of Ethyl L-pyroglutamate (7149-65-7):
XLogP3-AA: -0.1
H-Bond Donor: 1
H-Bond Acceptor: 3
Systematic Name: Ethyl (2S)-5-oxopyrrolidine-2-carboxylate
SMILES: O=C(OCC)[C@H]1NC(=O)CC1
InChI: InChI=1/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1
InChIKey: QYJOOVQLTTVTJY-YFKPBYRVBB
Std. InChI: InChI=1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1
Std. InChIKey: QYJOOVQLTTVTJY-YFKPBYRVSA-N
Ethyl L-pyroglutamate Toxicity Data With Reference
Carcinogenicity of Ethyl L-pyroglutamate (7149-65-7) hasn't been listed as a carcinogen by NTP, IARC,ACGIH, or CA Prop 65. And its toxicological properties have not been fully investigated.
Ethyl L-pyroglutamate Safety Profile
Hazard Codes: Xi.gif){kind=small}
Risk Statements:
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
Ethyl L-pyroglutamate Specification
Ethyl L-pyroglutamate (7149-65-7) also can be called (S)-5-Oxoproline ethyl ester ; Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate ; Ethyl 5-oxo-2-pyrrolidinecarboxylate ; Aclaplastin ;L-Pyroglutamic acid ethyl ester.It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.Notes to physician: Treat supportively and symptomatically.
In addition, Ethyl L-pyroglutamate (7149-65-7) is not compatible with strong oxidizing agents,strong bases, and you must not take it with incompatible materials.And also prevent it to broken down into hazardous decomposition products: oxides of nitrogen,carbon dioxide,carbon monoxide.
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