Ethyl D-(-)-pyroglutamate
- Product Name
- Ethyl D-(-)-pyroglutamate
- CAS No.
- 68766-96-1
- Chemical Name
- Ethyl D-(-)-pyroglutamate
- Synonyms
- D-PYR-OET;H-D-PYR-OET;H-D-PGLU-OET;ETHYL PYROGLUTAMATE;ETHYL 5-OXO-D-PROLINE;(R)-ETHYLPYROGLUTAMATE;Ethyl D-(-)-pyroglutamate;D-Pyroglutamic ethyl ester;5-Oxo-D-proline Ethyl Ester;D-Pyroglutamate ethyl ester
- CBNumber
- CB5770706
- Molecular Formula
- C7H11NO3
- Formula Weight
- 157.17
- MOL File
- 68766-96-1.mol
Ethyl D-(-)-pyroglutamate Property
- Melting point:
- 53-57 °C
- Boiling point:
- 176 °C12 mm Hg(lit.)
- alpha
- 3.5 º (C=5, H2O)
- Density
- 1.2483 (rough estimate)
- refractive index
- n20/D 1.478(lit.)
- Flash point:
- >230 °F
- storage temp.
- Sealed in dry,2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 14.78±0.40(Predicted)
- color
- White to Light Brown
- optical activity
- [α]/D 4.0±1°, c = 10 in ethanol
- BRN
- 82622
- CAS DataBase Reference
- 68766-96-1(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 309788
- Product name
- Ethyl (R)-(?)-2-pyrrolidone-5-carboxylate
- Purity
- 98%
- Packaging
- 1g
- Price
- $60.1
- Updated
- 2022/05/15
- Product number
- 309788
- Product name
- Ethyl (R)-(?)-2-pyrrolidone-5-carboxylate
- Purity
- 98%
- Packaging
- 5g
- Price
- $285
- Updated
- 2022/05/15
- Product number
- E901275
- Product name
- (R)-(-)-5-Ethylcarboxyl-2-pyrrolidinone
- Packaging
- 5g
- Price
- $65
- Updated
- 2021/12/16
- Product number
- E901275
- Product name
- (R)-(-)-5-Ethylcarboxyl-2-pyrrolidinone
- Packaging
- 1g
- Price
- $50
- Updated
- 2021/12/16
- Product number
- 04448
- Product name
- D-Pyroglutamicacidethylester,≥98%(NMR)
- Purity
- ≥98%(NMR)
- Packaging
- 5G
- Price
- $58.24
- Updated
- 2021/12/16
Ethyl D-(-)-pyroglutamate Chemical Properties,Usage,Production
Chemical Properties
Waxy Solid
Uses
(R)-(-)-5-Ethylcarboxyl-2-pyrrolidinone (cas# 68766-96-1) is a compound useful in organic synthesis.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
64-17-5
4042-36-8
68766-96-1
General procedure for the synthesis of D-pyroglutamic acid ethyl ester from ethanol and D-(+)-pyroglutamic acid: thionyl chloride (10 ml, 139.68 mmol) was slowly added to an ethanolic solution (100 ml) of D-(+)-pyroglutamic acid (10 g, 69.84 mmol; purchased from Aldrich, Art. No. 422614) which was cooled down to -5 °C. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was removed by vacuum evaporation and the residue was dissolved in ethyl acetate (350 ml). The organic phase was washed sequentially with water/triethylamine (40/12 ml) and water (40 ml). The organic phases were combined and concentrated by drying with anhydrous sodium sulfate. The concentrate was separated by column chromatography on a SNAP-Si column (50 g) with the eluent dichloromethane/ethyl acetate (gradient elution from 90/10 to 50/50). The fraction containing the target product was collected and the solvent was evaporated to give the first batch of ethyl D-pyroglutamate (D23) (6.4 g). The aqueous phase was saturated with sodium chloride and extracted with ethyl acetate (400 ml). The organic phase was washed with water (20 ml), dried over anhydrous sodium sulfate and concentrated to give the second batch of ethyl D-pyroglutamate (D23) (3.7 g). The product was characterized by 1H NMR (400 MHz, CDCl3), δ (ppm): 6.58 (broad single peak, 1H), 4.29-4.17 (multiple peaks, 3H), 2.53-2.29 (multiple peaks, 3H), 2.28-2.17 (multiple peaks, 1H), 1.35-1.22 (triple peaks, 3H).
References
[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1368 - 1381
[2] Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1760 - 1765
[3] Patent: WO2011/79114, 2011, A1. Location in patent: Page/Page column 81
[4] Patent: WO2013/4290, 2013, A1. Location in patent: Page/Page column 51; 52
[5] Patent: US2014/58117, 2014, A1. Location in patent: Paragraph 0049-0050
Ethyl D-(-)-pyroglutamate Preparation Products And Raw materials
Raw materials
Preparation Products
Ethyl D-(-)-pyroglutamate Suppliers
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View Lastest Price from Ethyl D-(-)-pyroglutamate manufacturers
- Product
- Ethyl D-(-)-pyroglutamate 68766-96-1
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-28
- Product
- Ethyl D-(-)-pyroglutamate 68766-96-1
- Price
- US $459.00/Kg/Bag
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 5000kg
- Release date
- 2021-06-07
- Product
- Ethyl D-(-)-pyroglutamate 68766-96-1
- Price
- US $7.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2018-12-24