N-Ethyl-L-glutamine
N-gamma-ethyl-L-glutamine
CAS: 3081-61-6
Molecular Formula: C7H14N2O3
N-Ethyl-L-glutamine - Names and Identifiers
| Name | N-gamma-ethyl-L-glutamine |
| Synonyms | Theanine L-Theanine H-GLN(ET)-OH H-GLU(NHET)-OH N-Ethyl-L-glutamin N-ethyl-L-glutamine N5-Ethyl-L-glutamine N'-Ethyl-L-glutamine L-Theanine 3081-61-6 N-gamma-ethyl-L-glutamine L-Theanine in stock GMP Factory L-GLUTAMIC ACID GAMMA-(ETHYLAMIDE) (S)-2-Amino-4-(N-ethylcarbamoyl)butanoic acid |
| CAS | 3081-61-6 |
| EINECS | 221-379-0 |
| InChI | InChI=1/C7H14N2O3/c1-2-9-6(10)4-3-5(8)7(11)12/h5H,2-4,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1 |
| InChIKey | DATAGRPVKZEWHA-YFKPBYRVSA-N |
N-Ethyl-L-glutamine - Physico-chemical Properties
| Molecular Formula | C7H14N2O3 |
| Molar Mass | 174.2 |
| Density | 1.171±0.06 g/cm3(Predicted) |
| Melting Point | 207°C |
| Boling Point | 430.2±40.0 °C(Predicted) |
| Specific Rotation(α) | +8.0°（water） |
| Flash Point | 214°C |
| Water Solubility | almost transparency |
| Solubility | Insoluble in ethanol and ether, easily soluble in water. |
| Vapor Presure | 1.32E-08mmHg at 25°C |
| Appearance | White crystal |
| Color | White |
| pKa | 2.24±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 2 months. |
| Refractive Index | 8 ° (C=5, H2O) |
| MDL | MFCD00059653 |
| Physical and Chemical Properties | White crystalline powder. Odorless, with slightly sweet taste, with taste threshold of 0.15%. Decomposition temperature of 214~215. Soluble in water, insoluble in ethanol, ether. Natural products are more present in the superior green tea (up to 2.2%). |
| Use | Used as a food additive |
N-Ethyl-L-glutamine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 43 - May cause sensitization by skin contact |
| Safety Description | S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. |
| HS Code | 29241990 |
N-Ethyl-L-glutamine - Reference
| Reference Show more | 1. Jin Xiaofang, Ma linlong, Liu Yanli, et al. Analysis of main biochemical components in six high amino acid tea cultivars [J]. Journal of tea science, 2017, 58(002):58-62. 2. Ma linlong Liu Yanli Cao Dan Liu Panpan Wang Shengpeng Huang Yong Ming Jin Xiaofang. Analysis and evaluation model construction of different tea varieties (lines) of green tea taste [J]. Journal of Agricultural Engineering 2020 36(10):277-286. 3. Liu Panpan, Gao Shiwei, Zheng Pengcheng, et al. Effect of infusion conditions on quality of Enshi Yulu green tea soup [J]. Science and Technology of Food Industry 2016(37):138-144. 4. Zhu Chengbo, Wu Xiaomei, Feng Lixia, Huang Xiangpeng, Peng Linjiang, Yang Hu-qing, Fang Zhengwei, Wang Ying, Lai Kuan, Zhang Yiming. Rapid determination of theanine in green tea by direct reading [J]. Tea Science, 2018,38(03):244-252. 5. Qi Wen, Zhang Haiwei, Zhang Zhengzhu. Effects of tea components on radiation degradation of endosulfan and bifenthrin [J]. Journal of Radiation Research and radiation processing, 2012, 30(004):203-208. 6. Qu Jingnian, niesue, Liu Xing, et al. Synthesis and thermochemistry of theanine complexes [J]. Journal of Hengyang Normal University, 2015. 7. Zhang Tingting, Zhang binle, Wang Shihuan, etc. Optimization of ultrasonic-assisted extraction of tea polyphenols from Wuyi Rock Tea stem [J]. Science and Technology of food industry, 2019, 40(16). 8. Jia-Jian Wang, Gao, Ya-rong, Liang, Lu, et al. Preparation of instant tea by enzymatic method [J]. Jiangsu Agricultural Sciences, 2012(03):260-262 9. Wang Tingting, Cai Zijian, Pu Wanxin et al. Analysis of sensory quality and main taste contributing components of Sichuan green tea [J]. Food Research and Development, 2018, 39(24):162-167. 10. Chen Hongxia, Li Ke, Lv Jie, etc. Determination and correlation analysis of active components in pile fermentation of pu-erh tea [J]. Journal of Beijing University of Chemical Technology (Natural Science), 2013, 40(005):84-87. 11. Zhang Yu, Zhang Xiaona, Xue Qiao Li, etc. Antioxidant effect of mistletoe extract in vitro [J]. The Journal of Light Industry, 2016, 31(003):39-48. 12. Du Huanhuan, Cai Yanni, Jiang Hai, etc. Simultaneous determination of eight effective compounds in tea by ultra performance liquid chromatography-tandem mass spectrometry [J]. Journal of Shaanxi University of Technology (Natural Science Edition), 2017(33):74-80. 13. Hu Xin, Wei Zhiming, Fang Shimao, Wang Yujie, Xu Shanshan, Ning Jingming. Study on continuous forming technology of granular Green Tea [J]. China Tea Processing, 2020(03):27-34. 14. Bai, Hui, et al. "L-theanine reduced the development of knee osteoarthritis in rats via its anti-inflammation and anti-matrix degradation actions: In vivo and in vitro study." Nutrients 12.7 (2020): 1988.https://doi.org/10.3390/nu12071988 15. [IF=4.952] Fengfeng Qu et al."Effect of different drying methods on the sensory quality and chemical components of black tea."Lwt Food Sci Technol. 2019 Jan;99:112 16. [IF=4.098] Chunlin Li et al."Rapid and non-destructive discrimination of special-grade flat green tea using Near-infrared spectroscopy."Spectrochim Acta A. 2019 Jan;206:254 17. [IF=7.514] Lizeng Cheng et al."Dynamic changes of metabolic profile and taste quality during the long-term aging of Qingzhuan Tea: The impact of storage age."Food Chem. 2021 Oct;359:129953 18. [IF=6.986] Shuai Guo et al."Enhancement of On-tissue Chemical Derivatization by Laser-Assisted Tissue Transfer for MALDI MS Imaging."Anal Chem. 2020;92(1):1431-1438 19. [IF=4.952] Jia Xue et al."Contrasting microbiomes of raw and ripened Pu-erh tea associated with distinct chemical profiles."Lwt Food Sci Technol. 2020 Apr;124:109147 20. [IF=4.952] Lizeng Cheng et al."Integration of non-targeted metabolomics and E-tongue evaluation reveals the chemical variation and taste characteristics of five typical dark teas."Lwt Food Sci Technol. 2021 Oct;150:111875 21. [IF=4.952] Huan Zhang et al."Label-free quantification proteomics reveals the active peptides from protein degradation during anaerobic fermentation of tea."Lwt Food Sci Technol. 2021 Oct;150:111950 22. [IF=4.511] Shuxian Zhao et al."Enhancing Effects of Theanine Liposomes as Chemotherapeutic Agents for Tumor Therapy."Acs Biomater Sci Eng. 2019;5(7):3373-3379 23. [IF=4.098] Chunlin Li et al."Discrimination of white teas produced from fresh leaves with different maturity by near-infrared spectroscopy."Spectrochim Acta A. 2020 Feb;227:117697 24. [IF=4.013] Longbao Li et al."Alteration of local and systemic amino acids metabolism for the inducible defense in tea plant (Camellia sinensis) in response to leaf herbivory by Ectropis oblique."Arch Biochem Biophys. 2020 Apr;683:108301 25. [IF=3.463] Hui Li et al."A rapid and efficient transient expression system for gene function and subcellular localization studies in the tea plant (Camellia sinensis) leaves."Sci Hortic-Amsterdam. 2022 Apr;297:110927 |
N-Ethyl-L-glutamine - What are the health benefits of L-theanine?
amino acids L-theanine (& gamma;-N-ethylglutamine), naturally present in tea leaves and Boletus Boletus (scientific name: xerocarus badius). Green Tea and Black Tea from the same plant. Black tea is produced by fermentation, while green tea is not. Green tea has been the main pillar of traditional Chinese medicine for more than three thousand years, and people use it together with other herbs as a medicinal agent, but also as a concentrated solution alone, aimed at enhancing endurance and concentration. The content of L-theanine depends on the place of growth, the method of production and the time of harvest of the tea tree. Different types of tea such as Pu-erh tea are higher in L-theanine content than the more well-known camellia tea . There is also a synthetic form of L-theanine (Suntheanine™).
L-theanine is widely used in Asian countries to combat various medical and mental health problems, and is rapidly gaining popularity in Western countries. Caffeine, another major component of tea, may raise levels of acetylcholine and dopamine in the brain, which may improve attention, cognition and mood. In terms of cognitive benefits, caffeine is more effective than L-theanine because it is absorbed more quickly, reaching peak plasma levels after 30 minutes, compared to the peak level of plasma after 50 minutes of ingestion of L-theanine. In addition to theanine and caffeine, tea contains other ingredients that may provide a variety of health benefits, including amino acids glutamine , arginine , serine, and alanine and phenolic compounds epigallocatechin, epicatechin gallate, epicatechin and epigallocatechin gallate (so-called 'catechin '). matcha tea is a special type of green tea product, it contains higher levels of beneficial phytochemicals than regular green tea.
animal and human studies have shown that L-theanine may reduce subjective stress responses, improve cognitive abilities, optimize sleep, and may be useful for chronic diseases, cardiovascular diseases, obesity and common cold have a protective effect. Various green tea ingredients, including L-theanine, caffeine and catechins, may help prevent metabolic syndrome and obesity. L-theanine may reduce oxidative damage caused by reactive oxygen species (I. E., "free radicals"), increase glutathione concentrations in the liver, and enhance the ability of liver enzymes such as superoxide dismutase to remove toxins from the blood. The results show that L-theanine may have anti-aging effect. Catechins from green tea may have beneficial antimicrobial and antivirus activity. In the gastrointestinal tract, green tea has been shown to potentially activate intracellular Antioxidant and suppresses the formation of pre-carcinogens.
Last Update：2024-01-02 23:10:35
N-Ethyl-L-glutamine - Introduction to the use of L-theanine
theanine (L-Theanine) is a unique free amino acid in tea, theanine is glutamic acid & gamma;-ethylamide, sweet. The content of theanine varies with the variety and position of tea. Theanine in dry tea 1-2 weight. Theanine in the chemical structure and brain active substance of glutamine, glutamic acid is similar, is the main component of the growth of emollient sweet tea.
function and use: Theanine is the characteristic amino acid of tea.
L-theanine is a seasoning. L-theanine is mainly used for green tea, the dosage is not specified. Nutrition Fortifier. Seasoning (the aroma component of green tea), the amount is not specified.
theanine is the amino acid with high content in tea, which accounts for more than 50% of the total free amino acids and 1-2% of the dry weight of tea. Theanine is a white needle-like body, soluble in water. With sweet and refreshing taste, is the taste of tea components. Japanese commonly used shading methods to improve the content of theanine in tea, in order to enhance the flavor of tea.
Food field
theanine has excellent processing characteristics and stability (under normal food processing conditions, such as sterilization, pH and heating, etc.), so it has a wide range of applications. At present, Japan has developed chocolate, jelly, pudding, chewing gum, health tea and various cool drinks added with theanine. In summary, theanine is mainly used in the following areas:
(1) as a quality improver of tea beverage, adding a certain amount of theanine in the production process of tea beverage can obviously improve the quality and flavor of tea beverage.
(2), as an additive to improve food flavor: Research shows that theanine can improve the bitter taste of coffee, cocoa, Korean ginseng beverage, grapefruit beverage, beer and so on, and reduce the astringency of wine, therefore, it can be used as a flavor improver for these foods.
(3), as a functional food additive: theanine has the effect of enhancing the intensity of alpha waves in the brain, making people feel relaxed and force, and has passed the human body test. Therefore, in the future, it can be added to food as a functional ingredient to develop functional foods for relieving nerve Nervousness and intelligence
Last Update：2024-01-02 23:10:35
N-Ethyl-L-glutamine - Introduction
L-theanine (L-Theanine) is a unique component in tea, a glutamine amino acid analog, and the most abundant amino acid in tea. Existed in green tea. It has a slightly sweet taste. Natural products are mostly found in superior green tea (up to 2.2%).
Last Update：2022-10-16 17:24:29
N-Ethyl-L-glutamine - Biological activity
L-theanine (L-Theanine) regulates the activity of several antitumor drugs. As a competitor of glutamine, theanine inhibits the growth of tumor cells by interfering with the metabolism of glutamine, and can enhance a variety of tumor cell drug treatment effect. L-theanine has an effect on human brain waves, which relaxes one's mood and reduces it by Nervousness. When L-theanine reversibly binds to NMDA receptor in nerve cells, it will cause the increase of intracellular Ca2 concentration, make the neural bond plasticity change, and effectively improve memory and learning.
Last Update：2023-08-16 21:32:38
N-Ethyl-L-glutamine - Reference Information
| Plant source: | Tea |
| Theanine | Theanine is a characteristic amino acid in tea. It is synthesized by glutamic acid and ethylamine in the root of tea tree under the action of theanine synthetase. It is an important substance that forms the taste of tea. It is mainly fresh and sweet, and is the main component of tea. 26 kinds of amino acids (6 non-protein amino acids) were identified in tea, generally accounting for 1% ~ 5% of the dry weight of tea, while theanine accounted for more than 50% of the total free amino acids in tea. tea tree amino acids refer to all 26 kinds of amino acids contained in tea, of which 20 kinds are protein-related amino acids, called protein amino acids; There are also 6 kinds of amino acids that have nothing to do with protein synthesis, which we call non-protein amino acids. These 6 kinds of tea are more important. The most important of these 6 kinds is theanine, so theanine is one of the amino acids and is also considered to be the characteristic amino acid of tea. as a characteristic non-protein amino acid with the highest content in tea, theanine is safe and non-toxic, and has a variety of biological activities such as anti-oxidation, immune regulation, anti-aging, antagonizing cellular excitotoxicity caused by excessive glutamate, etc. At the same time, L-theanine, as an alkylamine, can activate γ-T immune cells to promote cell proliferation and cytokine secretion, enhance the ability to resist tumor cells, reduce the infection of external microorganisms, and reduce the body's risk of colds and influenza. |
| introduction | theanine is an amino acid only contained in tea, and tea contains the most theanine content. L-theanine is synthesized in the roots of tea trees, transferred to the leaves through the branches, and accumulated in the leaves. Theanine will be converted into catechin under sunlight, so L-theanine is in high-grade green tea cultivated under light The content is higher, but the content in general crude tea leaves is less, and the content of polyphenols is higher. |
| consumption | ≤ 0.4g/day |
| applicable food category | the scope of use does not include infant food. |
| approval date | 2014-07-18 |
| Announcement No. | No. 15 of 2014 |
| announcement title | announcement on approving tea theanine as a new food raw material, etc. |
| Character | yellow powder |
| Theanine content (g/100g) | ≥20 |
| Moisture (g/100g) | ≤8 |
| identification test | take 1g of sample, add 10ml of 6mol/L hydrochloric acid, install a reflux condensing device, heat reflux on a water bath for 6h, add water to 20ml, and use this as sample liquid. Take 1ml of the above sample solution, add water to 50ml, add 5 μ1(GT-10) of this solution on chromatographic paper, and use n-butanol: glacial acetic acid: water = 5:1:2 to form an expanded solvent for paper chromatographic analysis. At the same time, the control liquid is used for chromatographic analysis as above. During chromatographic analysis, the spread distance is about 30cm, and the corresponding spots can be obtained. After unfolding, air dry, dry at 100 ℃ for 20min, spray with indantrione saturated n-butanol solution (0.2%), heat at 100 ℃ for 5min to make it color, and observe under natural light. The control solution was dissolved in 0.5mol/L hydrochloric acid from 0.1g L-sodium glutamate and fixed to 100ml, and 5/11 was taken as chromatographic solution. Take 5ml of the above sample solution, put it into a test tube, add 2g of sodium hydroxide, take a red litmus test strip moistened with water, hang it in the tube, plug the nozzle, heat the test tube in a water bath for 5min, and the litmus test strip strain is blue. |
| content analysis | 350mg of sample after drying at l00 ℃ for 3h is taken, dissolved in 3ml of formic acid and 50ml of glacial acetic acid, 2 drops of crystal violet test solution (TS-74) is added, and titrated with 0.1mol/L perchloric acid solution to the blue-green end point. At the same time, a blank test was conducted. Perchloric acid is equivalent to theanine (C7Hl4N2O3)17.42mg per m10.1mol/L. |
| toxicity | GRAS(FDA,§ 172.320,2000). |
| use | seasoning. Mainly used for green tea, the dosage is not specified. Nutritional enhancers. Seasoning (the aroma component of green tea), the dosage is not specified. Used as a food additive The sedative effect when added to food, the flavor improvement effect of L-theanine, enhancing immunity, lowering blood pressure, improving the brain, promoting the brain's learning and memory functions, and effectively enhancing the liver Detoxification function The antihypertensive effect of theanine The analog of glutamine is also one of the components of green tea. It can bind to AMPA, potassium magnesium alum and NMDA glycine receptors of rat cortical neurons but its affinity is lower than glutamate. It has been studied as an inhibitor of glutamate transport to prevent the uptake of glutamate by M5076 ovarian sarcoma-bearing mouse cells and to increase the effect of doxorubicin on tumor growth in M5076 mice. |
| Production method | L-glutamic acid is heated under high pressure to obtain pyrrolidone carboxylic acid. It is made into a copper salt, then anhydrous ethylamine is added, and then heated under high pressure to obtain L-theanine. Pyrrolidone carboxylic acid is obtained by heating L-glutamic acid under high pressure, adding anhydrous aminoethane, and then heating under high pressure. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:11:58
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View History
N-Ethyl-L-glutamine
8-羟基喹啉-2-腈
DPCPX, PD 116,948
苯基锡醋酸盐
外消旋氯卡色林游离碱
135112-28-6
水合碳酸钇(III), REacton
2-氯吡啶-4-羰基氯
3-苯基丙烯酰氯
4-Amino thioanisole
8-羟基喹啉-2-腈
DPCPX, PD 116,948
苯基锡醋酸盐
外消旋氯卡色林游离碱
135112-28-6
水合碳酸钇(III), REacton
2-氯吡啶-4-羰基氯
3-苯基丙烯酰氯
4-Amino thioanisole