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L-Theanine
- Iupac Name：(2S)-2-amino-5-(ethylamino)-5-oxopentanoic acid
- CAS No.: 3081-61-6
- Molecular Weight：174.2
- Modify Date.: 2022-11-29 11:00
- Introduction: Theanine is an abundant non-protein derived amino acid that was first isolated from green tea leaves in the late 1940s by Sakato[1]. Theanine has been named as 2-amino-4-[ethylcarbamoyl]butyric acid by the International Union of Pure and Applied Chemistry [IUPAC]. However, it has also been referred to as γ -glutamylethylamide, 5-N-ethylglutamine, γ -glutamyl-L-ethylamide, γ -ethylamino-L-glutamic acid and γ -L-glu-ethylamide.2–5 Similar to other amino acids in nature, theanine is a chiral species and occurs in nature predominantly as the L-[S]enantiomer [Fig. 1], while synthetic theanine is normally prepared as a racemic mixture of Land D-forms[2].Theanine is responsible for a unique taste constituent of the tea, producing a caramel flavor and an attractive aroma and that helps to alleviate tea polyphenols astringency and caffeine bitterness[3]. Technical, safety and toxicological evaluation suggested that theanine is a safe and non-toxic photogenic food supplement. L-theanine was synthesized chemically for the first time from aqueous ethylamine and pyrrolidone carboxylic acid[4]. L-theanine has been studied as a food additive and functional food in relation to human nutrition. It has noticeable bioactivities including anti-cerebral ischemia-reperfusion injury, stress-reducing, antitumor, anti-aging, and anti-anxiety activities[5, 6]. Cooper[7]stated that dietary supplementation of L-theanine is a feasible way to mitigate reactive oxygen species [ROS]-induced damage.Theanine is considered to be a unique amino acid in nature because, with the exception of being found in the basidiomycete mushroom Xerocomus badius, its occurrence appears to be limited to the Camellia genus, mostly the tea-producing plants C. sinensis var. sinensis and C. sinensis var. assamica and some closely related species such as C. japonica and C. sasanqua[8]In the leaves of the tea plant species, theanine accounts for about 500 g kg−1 of the free amino acids. Many of these amino acids are involved in producing the distinctive aroma and taste of tea and theanine has been linked with giving tea its distinctive umami taste[9]Because of its contribution to taste, the theanine content in tea leaves correlates highly with tea quality and price; the teas with a high content of theanine are normally evaluated as having a higher quality and thus command a higher price[10]. Theanine occurs in the cotyledons, shoots and roots of the tea plant seedling and it is biosynthesized from glutamic acid and ethylamine via the enzyme theanine synthetase[11].
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1. Names and Identifiers
- 1.1 Name
- L-Theanine
- 1.2 Synonyms
(2S)-2-Amino-4-(ethylcarbamoyl)butanoic acid (2S)-2-Azaniumyl-5-(ethylamino)-5-oxopentanoate (5Z)-5-(Ethylimino)-5-hydroxy-L-norvaline (S)-2-Amino-5-(ethylamino)-5-oxopentanoic acid EINECS 221-379-0 Glutamine, N-ethyl-, L- Glutamine,N-ethyl-, L- (6CI,7CI,8CI) L-Glutamic acid Γ-(ethylamide) L-Glutamine, N-ethyl- L-Norvaline, 5-(ethylimino)-5-hydroxy-, (5Z)- L-TheaMine L-Theanine (Ngamma-ethyl-L-glutamine) L-Γ-Glutamylethylamide MFCD00059653 N(5)-ethyl-L-glutamine N(5)-ethyl-L-glutamine zwitterion N5-ethylglutamine N5-Ethyl-L-glutamine N'-Ethyl-L-glutamine N-Ethyl-L-glutamine Ng-Ethyl-L-glutamine NSC 21308 N-Γ-ethyl-L-glutamine Nγ-Ethyl-L-glutamine Suntheanine Suntheanine CG 100 Theanin Theanine THEANINE,L
- 1.3 CAS No.
- 3081-61-6
- 1.4 CID
- 439378
- 1.5 EINECS(EC#)
- 221-379-0
- 1.6 Molecular Formula
- C7H14N2O3 (isomer)
- 1.7 Inchi
- InChI=1S/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
- 1.8 InChkey
- DATAGRPVKZEWHA-YFKPBYRVSA-N
- 1.9 Canonical Smiles
- CCNC(=O)CCC(C(=O)O)N
- 1.10 Isomers Smiles
- CCNC(=O)CC[C@@H](C(=O)O)N
2. Properties
- 2.1 Density
- 1.171
- 2.1 Melting point
- 207°C
- 2.1 Boiling point
- 427.1 °C at 760 mmHg
- 2.1 Refractive index
- 8 ° (C=5, H2O)
- 2.1 Flash Point
- 212.1 °C
- 2.1 Precise Quality
- 174.10000
- 2.1 PSA
- 92.42000
- 2.1 logP
- 0.40580
- 2.1 AnalyticLaboratory Methods
- HPLC determination in tea leaves.
- 2.2 Appearance
- Solid
- 2.3 Chemical Properties
- Theanine, like the protein-based amino acids, exists as a zwitterionic species and is a colorless crystalline solid [needles, melting point 214–216 ?C][2]. Studies on the buffering capacity of green tea extracts suggest the pKa of the theanine amino group to be[10, 12]. The pKa of the carboxyl unit was not formally quantified due to interference from other acidic species. However, comparisons with close structural analogues such as glutamine suggest the value lies in the range 2.1–2.5[13]Theanine is stable under acidic conditions but undergoes base hydrolysis to yield glutamic acid and ethylamine[2, 14]. During infusion, theanine does not react chemically with any of the other tea components. This is in contrast to catechins, which can precipitate from solution as a result of π stacking interactions with caffeine[15, 16]or can react with proteins and enzymes such as lipoxygenase, α-amylase, pepsin, trypsin and lipase[15].Of the tea components, theanine exhibits a higher water solubility [385 g L−1 at 0 ?C, 556 g L−1 at 100 ?C]than caffeine [21.7 g L−1]and the catechins [e.g. epigallocatechin gallate, 5 g L−1]; this permits a very effective diffusion of theanine from tea during hot-water infusions [2, 17]. The relative insolubility of theanine in organic solvents such as methanol and chloroform allows for its easy separation from caffeine and the catechins, which possess a molecular rather than a zwitterionic structure[2].Theanine has a complex umami taste[18-20].It also exhibits a synergism with the common umami flavouring agents monosodium glutamate and the purine nucleoside inosine 5’-monophosphate, which leads to an enhancement of the umami taste experience[18].The term umami is a Japanese-derived expression and it is classified as the fifth taste after sweet, salt, bitter and sour[19, 20]. Most of the typical umami substances are divided into two groups: L-α-amino acids, usually represented by monosodium glutamate and 5’-ribonucleotides and their derivatives, usually represented by inosine 5’-monophosphate or disodium 5’-guanylate[19, 20].
- 2.4 Color/Form
- Powder
- 2.5 Odor
- None (no odor)
- 2.6 PH
- pH of 5-6 (1% solution)
- 2.7 Physical
- Solid
- 2.8 pKa
- 2.24±0.10(Predicted)
- 2.9 Water Solubility
- Insoluble in ethanol and ether
- 2.10 Stability
- Product is considered stable and hazardous polymerization will not occur.
- 2.11 StorageTemp
- Store at?0-5°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A N5-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea.
- 3.2 General Description
- Theanine is an abundant non-protein derived amino acid that was first isolated from green tea leaves in the late 1940s by Sakato[1]. Theanine has been named as 2-amino-4-[ethylcarbamoyl]butyric acid by the International Union of Pure and Applied Chemistry [IUPAC]. However, it has also been referred to as γ -glutamylethylamide, 5-N-ethylglutamine, γ -glutamyl-L-ethylamide, γ -ethylamino-L-glutamic acid and γ -L-glu-ethylamide.2–5 Similar to other amino acids in nature, theanine is a chiral species and occurs in nature predominantly as the L-[S]enantiomer [Fig. 1], while synthetic theanine is normally prepared as a racemic mixture of Land D-forms[2].Theanine is responsible for a unique taste constituent of the tea, producing a caramel flavor and an attractive aroma and that helps to alleviate tea polyphenols astringency and caffeine bitterness[3]. Technical, safety and toxicological evaluation suggested that theanine is a safe and non-toxic photogenic food supplement. L-theanine was synthesized chemically for the first time from aqueous ethylamine and pyrrolidone carboxylic acid[4]. L-theanine has been studied as a food additive and functional food in relation to human nutrition. It has noticeable bioactivities including anti-cerebral ischemia-reperfusion injury, stress-reducing, antitumor, anti-aging, and anti-anxiety activities[5, 6]. Cooper[7]stated that dietary supplementation of L-theanine is a feasible way to mitigate reactive oxygen species [ROS]-induced damage.Theanine is considered to be a unique amino acid in nature because, with the exception of being found in the basidiomycete mushroom Xerocomus badius, its occurrence appears to be limited to the Camellia genus, mostly the tea-producing plants C. sinensis var. sinensis and C. sinensis var. assamica and some closely related species such as C. japonica and C. sasanqua[8]In the leaves of the tea plant species, theanine accounts for about 500 g kg−1 of the free amino acids. Many of these amino acids are involved in producing the distinctive aroma and taste of tea and theanine has been linked with giving tea its distinctive umami taste[9]Because of its contribution to taste, the theanine content in tea leaves correlates highly with tea quality and price; the teas with a high content of theanine are normally evaluated as having a higher quality and thus command a higher price[10]. Theanine occurs in the cotyledons, shoots and roots of the tea plant seedling and it is biosynthesized from glutamic acid and ethylamine via the enzyme theanine synthetase[11].
- 3.3 GHS Classification
- Signal: Warning
GHS Hazard StatementsAggregated GHS information provided by 62 companies from 2 notifications to the ECHA C&L Inventory.
Reported as not meeting GHS hazard criteria by 35 of 62 companies. For more detailed information, please visit
ECHA C&L websiteOf the 1 notification(s) provided by 27 of 62 companies with hazard statement code(s):
H317 (100%): May cause an allergic skin reaction [
Warning Sensitization, Skin]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Precautionary Statement Codes
P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501
- 3.4 Polymerization
- Product is considered stable and hazardous polymerization will not occur.
- 3.5 Usage
- cognitive enhancer
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R43
- 4.1 Safety Statements
- S28;S36/37
- 4.1 Hazard Declaration
- H317
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P280
- 4.1 Safety
-
Hazard Codes?
Xi
Risk Statements 43
R43:May cause sensitization by skin contact.
Safety Statements 28-36/37
S28:After contact with skin, wash immediately with plenty of soap-suds.?
S36/37:Wear suitable protective clothing and gloves.
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
6. Computational chemical data
- Molecular Weight: 174.2g/mol
- Molecular Formula: C7H14N2O3
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 174.10044231
- Monoisotopic Mass: 174.10044231
- Complexity: 170
- Rotatable Bond Count: 5
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 92.4
- Heavy Atom Count: 12
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBjMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAACCjBgAQCCALAAgAIAAGQGAAAAAAAAAAAAIGIAAACABIAgAAEQAAEFgCAAACcFwIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
7. Question & Answer
-
L-theanine is an amino acid found most commonly in tea leaves and in small amounts in Bay Bolete mushrooms. It can be found in both green and black tea. It’s also available in pill or tablet form at many drugstores. Research indicates that L-theanine promotes relaxation without drowsiness. Ma...
-
L-theanine is an amino acid. The human body does not produce this compound, and it is not essential for humans. Green tea, black tea, and certain types of mushroom naturally contain L-theanine. L-theanine may affect the levels of certain chemicals in the brain. These include serotonin and dopamine,...
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