02 L-theanine powder (3081-61-6) video
03 L-theanine powder Base Information
|Chemical name||L-γ-glutamylethylamide; N5-ethyl-L-glutamine|
|Molecular Weight||174.20 g/mol|
|Melting Point||174.20 °C|
|Appearance||White to Off-white powder|
|Half Life||1.2 hours|
|Solubility||L-Theanine is slightly soluble (in water) and a moderately acidic compound (based on its pKa).|
|Storage Condition||0 – 4 C for short term (days to weeks), or -20 C for long term (months).|
|Application||L-theanine in reducing acute stress and anxiety inpeople with stressful conditions.|
04 L-theanine (3081-61-6) General Description
L-Theanine powder, also known as L-gamma-glutamylethylamide or N-gamma-ethyl-L-glutamine, is a member of the class of compounds known as glutamine and derivatives. These compounds contain glutamine or a derivative thereof resulting from a reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Theanine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-Theanine can be found in saliva. The regulatory status of theanine varies by country. In Japan, L-theanine has been approved for use in all foods, including herb teas, soft drinks, and desserts. Restrictions apply to infant foods. In the United States, the Food and Drug Administration (FDA) considers it to be generally recognized as safe (GRAS) and allows its sale as a dietary supplement. The German Federal Institute for Risk Assessment, an agency of their Federal Ministry of Food and Agriculture, objects to the addition of L-theanine to beverages. The European Food Safety Authority EFSA advised negatively on health claims related to L-theanine and cognitive function, alleviation of psychological stress, maintenance of normal sleep, and reduction of menstrual discomfort. Therefore, health claims for L-theanine are prohibited in the European Union . L-Theanine is found in mushrooms and is a constituent of tea (Thea sinensis) and of the fungus Imleria badia. L-Theanine has been shown to exhibit neuroprotectant and neuroprotective functions.
05 L-theanine (3081-61-6) powder History
Theanine powder, also known as L-γ-glutamylethylamide and N5-ethyl-L-glutamine, is an amino acid analogue of the proteinogenic amino acids L-glutamate and L-glutamine and is found primarily in particular plant and fungal species. It was discovered as a constituent of green tea in 1949 and in 1950 was isolated from gyokuro leaves. Theanine provides a unique brothy or savory (umami) flavor to green tea infusions.
The name “theanine” without a prefix generally implies the enantiomer L-theanine, which is the form found in tea leaves and as a dietary supplement ingredient. Most studies have used L-theanine. The opposite enantiomer, D-theanine, has been studied less.
The regulatory status of theanine varies by country. In Japan, L-theanine has been approved for use in all foods, including herb teas, soft drinks, desserts, etc. Restrictions apply to infant foods. In the United States, the Food and Drug Administration (FDA) considers it to be generally recognized as safe (GRAS) and allows its sale as a dietary supplement. The German Federal Institute for Risk Assessment, an agency of their Federal Ministry of Food and Agriculture, objects to the addition of L-theanine to beverages. The European Food Safety Authority EFSA advised negatively on the use of L-theanine for improving cognitive function, alleviation of psychological stress, maintenance of normal sleep, and reduction of menstrual discomfort. Therefore, health claims for L-theanine are not recognized in the European Union.
06 L-theanine (3081-61-6) Mechanism Of Action
The chemical name N5-ethyl-L-glutamine and other synonyms for theanine reflect its chemical structure. The name theanine, without prefix, is generally understood to imply the L- (S-) enantiomer, derived from the related proteinogenic L-amino acid glutamic acid. Theanine is an analog of this amino acid, and its primary amide, L-glutamine (also a proteinogenic amino acid). Theanine is a derivative of glutamine that is ethylated on the amide nitrogen (as the name N5-ethyl-L-glutamine describes), or alternatively, to the amide formed from ethylamine and L-glutamic acid at its γ- (5-) side chain carboxylic acid group (as the name γ-L-glutamylethylamide describes).
Relative to theanine, the opposite (D-, R-) enantiomer is largely absent from the literature, except implicitly. While natural extracts that are not harshly treated are presumed to contain only the biosynthetic L- enantiomeric form, mishandled isolates and racemic chemical preparations of theanines necessarily contain both theanine and its D-enantiomer (and from racemic syntheses, in equal proportion), and studies have suggested that the D-isomer may actually predominate in some commercial supplement preparations. Amino acid racemization in aqueous media is a well-established chemical process promoted by elevated temperature and non-neutral pH values; prolonged heating of Camellia extracts—possible for oversteeped teas and in undisclosed commercial preparative processes—has been reported to result in increasing racemization of theanine to give increasing proportions of the nonnatural D-theanine, up to equal proportions of each enantiomer.
07 L-theanine (3081-61-6) Application
Able to cross the blood–brain barrier, theanine has reported psychoactive properties. Theanine has been studied for its potential ability to reduce mental and physical stress, improve cognition, and boost mood and cognitive performance in a synergistic manner with caffeine.
A Natural Standard monograph that reviews current research on theanine reports that it is likely safe in doses of 200–250 mg up to a maximum daily dose of 1,200 mg. Though some people use theanine for these purposes, Natural Standard rates the evidence to support the usage for anxiety reduction, blood pressure control, and mood improvement as “unclear or conflicting scientific evidence” and the evidence for improved cognition as “fair negative scientific evidence”. Many of the studies of theanine were done in combination with caffeine as found in tea. While the studies found that the combination had some effect on mood, the studies found that theanine alone had little effect. A review by other researchers of a small set of trials concluded that there are benefits of L-theanine in reducing acute stress and anxiety in people with stressful conditions.
08 L-theanine (3081-61-6) More research
A study of teabags sold in British supermarkets in 2011 found that the teabags containing the most L-theanine per cup (24 mg versus 8 mg per cup) were the lower-quality brands containing black tea, with a supermarket brand of black tea having the highest theanine content. The study demonstrates that brewing time was not a significant factor in L-theanine extraction from the teabags, with most theanine extracted within a short period of time. Addition of sugar and small quantities of milk make no significant difference, while larger quantities of milk reduced the measured theanine content.
09 L-theanine (3081-61-6) Document Download
10 L-theanine (3081-61-6) Reference
Nagasawa K, Aoki H, Yasuda E, Nagai K, Shimohama S, Fujimoto S (2004). “Possible involvement of group I mGluRs in neuroprotective effect of theanine”. Biochem. Biophys. Res. Commun. 320 (1): 116–22.
Sugiyama T, Sadzuka Y, Tanaka K, Sonobe T (2001). “Inhibition of glutamate transporter by theanine enhances the therapeutic efficacy of doxorubicin”. Toxicol. Lett. 121 (2): 89–96.
Sugiyama T, Sadzuka Y (2003). “Theanine and glutamate transporter inhibitors enhance the antitumor efficacy of chemotherapeutic agents”. Biochim. Biophys. Acta. 1653 (2): 47–59.
- 01. Overview
- 02. L-theanine powder (3081-61-6) video
- 03. L-theanine powder Base Information
- 04. L-theanine (3081-61-6) General Description
- 05. L-theanine (3081-61-6) powder History
- 06. L-theanine (3081-61-6) Mechanism Of Action
- 07. L-theanine (3081-61-6) Application
- 08. L-theanine (3081-61-6) More research
- 09. L-theanine (3081-61-6) Document Download
- 10. L-theanine (3081-61-6) Reference