5-oxo-L-proline
(S)-(-)-2-Pyrrolidone-5-carboxylic acid
CAS: 98-79-3
Molecular Formula: C5H7NO3
5-oxo-L-proline - Names and Identifiers
5-oxo-L-proline - Physico-chemical Properties
| Molecular Formula | C5H7NO3 |
| Molar Mass | 129.11 |
| Density | 1.3816 (rough estimate) |
| Melting Point | 160-163°C(lit.) |
| Boling Point | 239.15°C (rough estimate) |
| Specific Rotation(α) | -27.5 º (c=10, 1 N NaOH) |
| Flash Point | 227.8°C |
| Water Solubility | 10-15 g/100 mL (20 ºC) |
| Solubility | Soluble in water, alcohol, acetone and glacial acetic acid, slightly soluble in ethyl acetate, insoluble in ether. |
| Vapor Presure | 0.002Pa at 25℃ |
| Appearance | White fine crystal |
| Color | White to off-white |
| Merck | 14,8001 |
| BRN | 82132 |
| pKa | 3.32(at 25℃) |
| PH | 1.7 (50g/l, H2O, 20℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with bases, acids, strong oxidizing agents. |
| Refractive Index | -10 ° (C=5, H2O) |
| MDL | MFCD00005272 |
| Physical and Chemical Properties | Melting point 152-162°C specific optical rotation -27.5 ° (c = 10, 1 N NaOH) water-soluble 10-15g/100 mL (20°C) |
| Use | Used in food, medicine, cosmetics and other industries |
5-oxo-L-proline - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | TW3710000 |
| FLUKA BRAND F CODES | 21 |
| TSCA | Yes |
| HS Code | 29337900 |
| Hazard Class | IRRITANT |
5-oxo-L-proline - Reference
| Reference Show more | 1. [IF=1.902] Zhi Rao et al."Multicomponent determination of traditional Chinese medicine preparation yin-zhi-huang injection by LC–MS/MS for screening of its potential bioactive candidates using HepaRG cells."Biomed Chromatogr. 2018 Feb;32(2):e4057 2. [IF=4.466] Yao Tan et al."Multiomics Integrative Analysis for Discovering the Potential Mechanism of Dioscin against Hyperuricemia Mice."J Proteome Res. 2021;20(1):645–660 3. [IF=4.142] Wang Chenxi et al."Systematic quality evaluation of Peiyuan Tongnao capsule by offline two-dimensional liquid chromatography/quadrupole-Orbitrap mass spectrometry and adjusted parallel reaction monitoring of quality markers."Anal Bioanal Chem. 2019 Nov;4 4. [IF=3.935] Biru Shi et al."Investigation on the stability in plant metabolomics with a special focus on freeze-thaw cycles: LC–MS and NMR analysis to Cassiae Semen (Cassia obtusifolia L.) seeds as a case study."J Pharmaceut Biomed. 2021 Sep;204:114243 |
5-oxo-L-proline - Basic information
oxidized proline is also known as L-pyroglutamic acid . Relative molecular mass 129.12. The melting point was 162-163 °c. Do not dissolve in ether, ethyl acetate-soluble, soluble in water (25 ° C 40), ethanol, acetone and acetic acid. Specific optical rotation -11.9 °(c = 2,H2O). Its sodium salt can be used as a moisturizing agent in cosmetics, its moisturizing effect is better than glycerol, sorbitol, non-toxic, no stimulating effect, for skin care and hair care cosmetics; This product has inhibitory effect on tyrosine oxidase, can prevent the deposition of melanin-like, has a whitening effect on the skin; Has a softening effect on the skin, can be used for nail cosmetics; Can also be used as a surfactant for detergents; Chemical reagents, for the resolution of racemic amines; Organic intermediates.
Chinese name
oxidized proline
foreign name
L-Pyroglutamic acid
alias
chemical formula
C5H7NO3
Molecular weight
129.12
CAS accession number
98-79-3
melting point
162~163℃
water-soluble
soluble in water (40 at 25 ℃)
Last Update：2024-01-02 23:10:35
5-oxo-L-proline - Comparative study on the contents of adenosine and L-pyroglutamic acid in fresh ginseng and its processed products
from VIP Journal Professional Edition
Author:
Ma Dongsheng , high fly , Li Wei , Xiaojie , Zheng Yi male
Abstract:
with six years of fresh ginseng, Raw ginseng, red ginseng as the test material, the establishment of adenosine and L-pyroglutamic acid content determination method: RP-HPLC method for the analysis of adenosine content in samples, elite Hypersil ODS2(4.6mm × 250, 5 μm) column, mobile phase was methanol-water (10:90), flow rate was 0.8 mL/min, detection wavelength was 260 nm, the column temperature was 40 ℃; The content of L-pyroglutamic acid in the sample was analyzed by the first method, the COSMOSIL 5C18-PAQ (RP-HPLC ×, 5 μm) column, the mobile phase consisted of methanol -5 mmol/L sodium acetate aqueous solution (8:92) with a flow rate of 0.5 mL/min, a detection wavelength of 210 nm and a column temperature of 40 ℃. The contents of adenosine and L-pyroglutamic acid in fresh ginseng and its processed products were 0.332-0.457 mg/g and 0.315-1.056 mg/g, respectively. The results showed that the contents of adenosine and L-pyroglutamic acid changed regularly in fresh ginseng and its processed products. The contents of adenosine and L-pyroglutamic acid in fresh ginseng were the highest, followed by the processed products. Therefore, in terms of anti-diabetic activity, fresh ginseng should have more research value than its processed products.
Key words:
fresh ginseng; Raw ginseng; Red ginseng; Adenosine; L-pyroglutamic acid
cited:
year:
2013
Last Update：2024-01-02 23:10:35
5-oxo-L-proline - Progress in asymmetric synthesis of L-pyroglutamic acid as chiral source
from VIP
Author:
Abstract:
The reaction characteristics of L-pyroglutamic acid as chiral source are introduced, and the application of L-pyroglutamic acid as chiral source in asymmetric synthesis is reviewed.
Key words:
Asymmetric Synthesis of L-pyroglutamic acid chiral source
DOI:
10.3969/j.issn.0441-3776.1998.09.003
cited:
year:
1998
Last Update：2024-01-02 23:10:35
5-oxo-L-proline - Determination of L-pyroglutamic acid in Gastrodia elata by high performance liquid chromatography
from VIP Journal Professional Edition
Author:
Abstract:
The components of L-pyroglutamic acid in Gastrodia elata Bl with different sources and processing methods were quantitatively analyzed by HPLC. The results showed that the content of L-pyroglutamic acid in Gastrodia elata was different due to different producing areas, cultivation methods and processing methods. The content of L-pyroglutamic acid in wild species and fresh products was higher than that in dry products.
Key words:
Gastrodia elata Blume L-pyroglutamic acid high performance liquid chromatography Traditional Chinese Medicine
cited:
year:
2000
Last Update：2024-01-02 23:10:35
5-oxo-L-proline - Introduction
Solubility in water: 10-15% (20°C), soluble in ethanol and acetone.
Last Update：2022-10-16 17:30:28
5-oxo-L-proline - Reference Information
| LogP | -1.233 at 20℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | pyroglutamic acid is 5-oxyproline. It is formed by dehydration between α-NH2 group and γ-hydroxyl group of glutamic acid to form a molecular lactam bond; It can also be formed by losing an Amido group in a glutamine molecule. If glutathione synthetase deficiency, can cause pyroglutamemia, a series of clinical symptoms. Pyroglutamemia is a disorder of organic acid metabolism caused by glutathione synthetase deficiency. Clinical manifestations of birth 12~24 hours of onset, progressive hemolysis, jaundice, chronic Metabolic Acidosis, mental disorders, etc.; Urine contains pyroglutamic acid, lactic acid, Alpha deoxy4 glycoloacetic acid lipid. Treatment, symptomatic, pay attention to adjust the diet after age. |
| properties | L-pyroglutamic acid, also known as L-pyroglutamic acid, L-pyroglutamic acid. From the ethanol and petroleum ether mixture in the precipitation of colorless orthorhombic double cone Crystal, melting point of 162~163 ℃. Soluble in water, alcohol, acetone and acetic acid, ethyl acetate-soluble, insoluble in ether. Specific optical rotation -11.9 °(c = 2,H2O). |
| Features and uses | in human skin contains a moisturizing function of water-soluble substances-natural moisturizing factor, its composition is roughly amino acid (containing 40%), pyroglutamic acid (containing 12%), inorganic salts (Na, K, Ca, Mg, etc. containing 18.5%), and other organic compounds (containing 29.5%). Therefore, pyroglutamic acid is one of the main components of skin natural moisturizing factor, and its moisturizing ability far exceeds that of glycerol and propylene glycol. And non-toxic, no stimulation, is a modern Skin Care, Hair Care cosmetics excellent raw materials. Pyroglutamic acid also has an inhibitory effect on the activity of tyrosine oxidase, thereby preventing the deposition of "melanoid" substances in the skin, which has a whitening effect on the skin. Has a softening effect on the skin, can be used for nail cosmetics. In addition to the application in cosmetics, L-pyroglutamic acid can also produce derivatives with other organic compounds, which have special effects on surface activity, transparent and bright effect, etc. It can also be used as a surfactant for detergents; Chemical reagents for the resolution of racemic amines; Organic intermediates. |
| preparation method | L-pyroglutamic acid is formed by removing one minute of water from the molecule of L-glutamic acid, and its preparation process is simple, the key steps are the control of temperature and dewatering time. (1) 500g of L-glutamic acid was added to a 100 ml beaker, and the beaker was heated with an oil bath, and the temperature was raised to 145 to 150 ° C., and the temperature was maintained for 45 minutes for dehydration reaction. The dehydrated solution was Tan. (2) after completion of the dehydration reaction, the solution was poured into boiling water with a volume of about 350, and the solution was completely dissolved in water. After cooling to 40 to 50 ° C., an appropriate amount of activated carbon was added for decoloration (repeated twice). A colorless transparent solution was obtained. (3) when the colorless transparent solution prepared in step (2) is directly heated and evaporated to reduce the volume to about half, turn to the water bath and continue to concentrate to a volume of about 1/3, you can stop heating, and in the hot water bath to slow the crystallization, 10 to 20 hours after the preparation of colorless prismatic crystals. The amount of L-pyroglutamic acid in cosmetics depends on the formulation. This product can also be used on cosmetics in the form of 50% concentrated solution. |
| glutamic acid | glutamic acid is an amino acid constituting a protein, has an ionized acidic side chain, and exhibits hydrotropism. Glutamic acid is susceptible to cyclization into pyrrolidone carboxylic acid, I .e., pyroglutamic acid. glutamic acid is particularly high in all cereal proteins, providing alpha-ketoglutarate through the tricarboxylic acid cycle. Alpha ketoglutaric acid can be directly synthesized from ammonia under the catalysis of glutamate dehydrogenase and NADPH (coenzyme II), and can also be catalyzed by aspartate aminotransferase or alanine aminotransferase, glutamic acid is produced by transamination of aspartic acid or alanine; In addition, glutamic acid can be reversibly transformed with proline and ornithine (from arginine), respectively. Glutamate is therefore a nutritionally non-essential amino acid. When glutamic acid is deaminated under the catalysis of glutamate dehydrogenase and NAD (coenzyme I) or is transferred out of the amino group under the catalysis of aspartate aminotransferase or alanine aminotransferase to produce alpha ketoglutarate, it enters the tricarboxylic acid cycle and generates sugars through the gluconeogenic pathway, so glutamic acid is an important glycogenic amino acid. glutamic acid in different tissues (such as muscle, liver, brain, etc.) can synthesize glutamine with NH3 through the catalysis of glutamine synthetase, it is the detoxification product of ammonia, especially in brain tissue, and also the storage and utilization form of ammonia in the body (see "glutamine and its metabolism"). glutamic acid is synthesized with acetyl-CoA as a cofactor of mitochondrial carbamoyl phosphate synthase (involved in the synthesis of urea) through the catalysis of acetyl-glutamate synthase. γ-aminobutyric acid (GABA) is a product of the decarboxylation of glutamic acid, especially in high concentrations in brain tissue, and also appears in the blood, its physiological function is considered to be inhibitory neurotransmitter, the antispasmodic and hypnotic effects exerted by the clinical infusion of echinocandin may be achieved through GABA. The catabolism of GABA enters the tricarboxylic acid cycle by converting GABA transaminase and aldehyde dehydrogenase into succinic acid to form a GABA shunt. |
| Use | used as intermediates in organic synthesis, food additives, etc. used in food, medicine, cosmetics and other industries |
| production method | there are semi-synthesis method, enzymatic conversion method and total synthesis method. At present, the main method of industrial production is the semi-synthesis of glutamic acid as raw material. A 42% aqueous solution of glutamic acid was heated at 140 ° C. For 3H to obtain a reaction solution containing L-pyroglutamic acid as a main component. After concentration under reduced pressure, crystallization, washing and drying, L-pyroglutamic acid was obtained at a conversion rate of 94%. |
Last Update：2024-04-09 21:01:54
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View History
5-oxo-L-proline
Bis(2-di-o-tolylphosphinophenyl)ether
36854-57-6
1269755-45-4
Propinoicanhydride
26194-57-0
160468-17-7
佩尔地平
17261-28-8
氧化镁(重质)
Bis(2-di-o-tolylphosphinophenyl)ether
36854-57-6
1269755-45-4
Propinoicanhydride
26194-57-0
160468-17-7
佩尔地平
17261-28-8
氧化镁(重质)