L-Theanine | Carboxylic Acids

L-theanine is an amino acid found most commonly in tea leaves and binds to ionotropic glutamate receptors in the micromolar range, including the AMPA and kainate receptors and, to a lesser extent, the NMDA receptor.

Synonyms: L-Glutamic Acid γ-ethyl amide; Nγ-Ethyl-L-glutamine; NSC 21308

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of Theanine Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of Theanine

CAS No. :	3081-61-6
Formula :	C₇H₁₄N₂O₃
M.W :	174.20
SMILES Code :	O=C(O)[C@@H](N)CCC(NCC)=O
Synonyms :	L-Glutamic Acid γ-ethyl amide; Nγ-Ethyl-L-glutamine; NSC 21308
MDL No. :	MFCD00059653
InChI Key :	DATAGRPVKZEWHA-YFKPBYRVSA-N
Pubchem ID :	439378

Safety of Theanine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317
Precautionary Statements:	P261-P280

Application In Synthesis of Theanine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 3081-61-6 ]

[ 3081-61-6 ] Synthesis Path-Downstream 1~35

1
[ 1499-55-4 ]
[ 75-04-7 ]
[ 3081-61-6 ]

References: [1]Amino Acids,2010,vol. 39,p. 1177 - 1182.
[2]Chemical and pharmaceutical bulletin,1971,vol. 19,p. 1301 - 1307.

2
[ 557-66-4 ]
[ 142-47-2 ]
[ 3081-61-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,2008,vol. 72,p. 1206 - 1211.
[2]Bioscience, Biotechnology and Biochemistry,1992,vol. 56,p. 708 - 711.
[3]Bioscience, Biotechnology and Biochemistry,1992,vol. 56,p. 708 - 711.
[4]Bioscience, Biotechnology and Biochemistry,2009,vol. 73,p. 2677 - 2683.

3
[ 56-85-9 ]
[ 75-04-7 ]
[ 3081-61-6 ]

References: [1]Process Biochemistry,2014,vol. 49,p. 1429 - 1439.
[2]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 1279 - 1283.
[3]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 481 - 483.
[4]Bioscience, Biotechnology and Biochemistry,2010,vol. 74,p. 1936 - 1939.
[5]RSC Advances,2014,vol. 4,p. 9021 - 9030.

4
[ 149834-97-9 ]
[ 3081-61-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,1992,vol. 56,p. 689.

5
[ 142-47-2 ]
[ 75-04-7 ]
[ 3081-61-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,2004,vol. 68,p. 1888 - 1897.
[2]Bioscience, Biotechnology and Biochemistry,2004,vol. 68,p. 1888 - 1897.

6
[ 67-56-1 ]
[ 3081-61-6 ]
C₈H₁₆N₂O₃*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 20℃; for 12h;	L-Theanine (5 g) (Sun<strong>[3081-61-6]theanine</strong>) was slurried in dry MeOH (50 ml). Then 5.145 g of Cl2SO were added drop-wise over 5 minutes (part way through the addition all of the solids dissolve to give a clear colourless solution) and the resulting solution was held for 12 hours at 20 C. to allow the reaction shown in scheme (II) to occur:

References: [1]Patent: US2008/9505,2008,A1 .Location in patent: Page/Page column 5.

7
[ 67-56-1 ]
[ 3081-61-6 ]
C₈H₁₆N₂O₃*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 20℃; for 12.08h;	Examples; EXAMPLE 1; This example demonstrates the manufacture of a compound of the invention (N-ethyl-3- [5- (2-ethylcarbamoyl-ethyl) -3, 6-dioxo- piperazin-2-yl] -propionamide; see formula (4)).; L-Theanine (5 g) (Sun<strong>[3081-61-6]theanine</strong>) was slurried in dry MeOH (50 ml). Then 5.145 g of CI2SO were added drop-wise over 5 minutes (part way through the addition all of the solids dissolve to give a clear colourless solution) and the resulting solution was held for 12 hours at 200C to allow the reaction shown in scheme (II) to occur:; MeOH, SO2 and HCl were then removed under vacuum to leave a thick clear oil to which dry MeOH (50 ml) was added. The pH was then raised by adding MeONa while testing pH by intermittently spotting onto wet indicator paper. After adding 3.17 g of MeONa, the pH had increased to >11, which resulted in the reaction shown in scheme (III) :; The resulting solution was held for 12 hours at 200C to allow the reaction shown in scheme (IV) to occur:The resulting suspension was then filtered to remove NaCl and the filtrate subjected to vacuum to remove MeOH. The product was a white solid.The product was analysed with LC-MS (Liquid-Chromatography coupled Mass Spectroscopy) under the following conditions:Column: Phenomonex Gemini 5mu C18 IIOA 150mm x 2.00mmSolvents: A: 0.1% Formic Acid / WaterB: 0.1% Formic Acid / AcetonitrileFlow rate: 0.2 ml / minuteColumn Temperature: 300C Stop Time: 25 minutes; Mass Spectrometer Detection:Selected Ion Recording at m/z 175.6 for Theanine. Selected Ion Recording at m/z 313.5 for Theanine dimer .The results showed that the product was free from <strong>[3081-61-6]theanine</strong> (retention time of <strong>[3081-61-6]theanine</strong> = 3.7 min) and had a characteristic new peak with a retention time of around 7.4 min.The high resolution proton NMR spectrum of the product in MeOD-d4 is shown in Figure 1.

References: [1]Patent: WO2008/3626,2008,A1 .Location in patent: Page/Page column 18-20.

8
[ 557-66-4 ]
[ 142-47-2 ]
[ 3081-61-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,2005,vol. 69,p. 784 - 789.
[2]Bioscience, Biotechnology and Biochemistry,2007,vol. 71,p. 545 - 552.

9
[ 340-90-9 ]
[ 3081-61-6 ]

References: [1]Organic Preparations and Procedures International,2004,vol. 36,p. 182 - 185.

10
[ 25830-77-7 ]
[ 3081-61-6 ]

References: [1]Organic Preparations and Procedures International,2004,vol. 36,p. 182 - 185.

11
[ 1676-73-9 ]
[ 3081-61-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,1992,vol. 56,p. 689.

12
[ 116027-39-5 ]
[ 3081-61-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,1992,vol. 56,p. 689.

13
[ 56-86-0 ]
[ 593-51-1 ]
[ 3081-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With boric acid;glutaminase; In water; at 30℃; for 22h;pH 11;	0.3 M glutamine and 1.5 M methylamine hydrochloride were reacted in the presence of 0.3 U glutaminase (commercially available) at 30 C. for 22 hours in a buffer solution of 0.05 M boric acid (pH 11), whereby 225 nm theanine was obtained. Reaction liquid was applied to Dowex 50×8 columnar chromatgraphy and Dowex 1×2 columnar chromatography (both made by Muromachi Chemical Co., Ltd.) thereby to be processed by ethanol, whereby an object substance is isolated from the reaction liquid. The isolated substance was applied to an amino acid analyzer (made by Hitachi Co.) and paper chromatography. Since the isolated substance behaved in the same way as a standard substance, it was recognized as L-theanine. When the isolated substance was processed by hydrolysis using hydrochloric acid or glutaminase, glutamine acid and ethylamine were produced in a ratio of 1:1. Thus, since the isolated substance was hydrolyzed by glutaminase, it was shown that ethylamine was gamma-ethylamine of glutamine acid. Furthermore, it was confirmed on the basis of glutamate dehydrogenase that glutamine acid produced by hydrolysis was L-glutamine acid. As a result, 8.5 g theanine was obtained.

References: [1]Patent: US2006/45905,2006,A1 .Location in patent: Page/Page column 3.

14
[ 75-04-7 ]
[ 3081-61-6 ]

References: [1]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 6-7.
[2]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 7-8.
[3]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 6.
[4]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 7.
[5]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 7.
[6]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 7.
[7]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 7.
[8]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 6.
[9]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 9.
[10]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 8.
[11]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 8-9.
[12]Patent: WO2006/82835,2006,A1 .Location in patent: Page/Page column 8.

15
[ 56-85-9 ]
[ 557-66-4 ]
[ 3081-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	glutaminase; In water; at 30℃; for 22h;pH 11;Aqueous boric buffer;	Example 1; Production of Theanine by an Enzymatic Method; 0.3 M glutamine and 1.5 M ethylamine hydrochloride in 0.05 M boric acid buffer (pH11) were reacted in the presence of 0.3 U glutaminase (commercial product) at 30 C. for 22 hours, and 225 nmol of L-theanine was obtained. Subsequently, the reaction solution was applied to Dowex 50×8 and Dowex 1×2 column chromatography (MUROMACHI CHEMICALS INC.), followed by ethanol treatment, to isolate the objective substance from the reaction solution. The isolated substance was analyzed by an amino acid analyzer (Hitachi, Ltd.) and paper chromatography, and was confirmed to be L-theanine due to the same pattern of movement as that of the standard substance. Hydrolysis treatment with hydrochloric acid or glutaminase produced glutamic acid and ethylamine at a ratio of 1:1. Thus, the isolated substance was hydrolyzed by glutaminase, demonstrating the binding of ethylamine at the gamma position of glutamic acid. L-glutamic acid generated by hydrolysis was confirmed by glutamate dehydrogenase. Thus, 8.5 g of L-theanine was obtained.

References: [1]Patent: US2006/217321,2006,A1 .Location in patent: Page/Page column 4.

16
[ 56-85-9 ]
[ 3081-61-6 ]
L-glutaminyl-L-theanine [ No CAS ]
L-theanyl-L-glutamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	glutaminase; In water; at 30℃; for 22h;pH 11;Aqueous boric buffer;	Example 6; Production of a Mixture of Theanyl-Glutamine and Glutaminyl-Theanine; 0.4 M L-<strong>[3081-61-6]theanine</strong> and 0.4 M L-glutamine in 0.05 M boric acid buffer (ph11) were reacted in the presence of 0.3 U glutaminase (commercial product) at 30 C. for 22 hours to obtain 120 nmol of a mixture of theanyl-glutamine and glutaminyl-<strong>[3081-61-6]theanine</strong>. Subsequently, the reaction solution was applied to Dowex 50×8 and Dowex 1×2 column chromatography (MUROMACHI CHEMICALS INC.) to isolate the objective substance from the reaction solution. Structural analysis was conducted on the theanyl-glutamine and glutaminyl-<strong>[3081-61-6]theanine</strong> by mass spectrum analysis and NMR for confirmation.

References: [1]Patent: US2006/217321,2006,A1 .Location in patent: Page/Page column 4.

17
[ 3081-61-6 ]
[ 910541-97-8 ]

Yield	Reaction Conditions	Operation in experiment
	glutaminase; In water; at 30℃; for 22h;pH 11;Aqueous boric buffer;	Example 4; Production of Theanyl-Theanine; 0.32 M L-<strong>[3081-61-6]theanine</strong> in 0.05 M boric acid buffer (pH11) was reacted in the presence of 0.3 U glutaminase (commercial product) at 30 C. for 22 hours, and 150 nmol of theanyl-<strong>[3081-61-6]theanine</strong> was obtained. Subsequently, the reaction solution was applied to Dowex 50×8 and Dowex 1×2 column chromatography (MUROMACHI CHEMICALS INC.) to isolate the objective substance from the reaction solution.

References: [1]Patent: US2006/217321,2006,A1 .Location in patent: Page/Page column 4.

18
[ 56-85-9 ]
[ 593-51-1 ]
[ 56-86-0 ]
[ 3081-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With glutaminase; water; boric acid; at 30℃; for 22h;pH 11;Enzymatic reaction;	0.3 M glutamine and 1.5 M methylamine hydrochloride were reacted in the presence of 0.3 U glutaminase (commercially available) at 30°C for 22 hours in a buffer solution of 0.05 M boric acid (pH 11), whereby 225 nm theanine was obtained. Reaction liquid was applied to Dowex 50.x.8 columnar chromatography and Dowex 1.x.2 columnar chromatography (both made by Muromachi Chemical Co., Ltd.) thereby to be processed by ethanol, whereby an object substance is isolated from the reaction liquid. As a result, 8.5 g theanine was obtained. The isolated substance was applied to an amino acid analyzer (made by Hitachi Co.) and paper chromatography. Since the isolated substance behaved in the same way as a standard substance, it was recognized as L-theanine. When the isolated substance was processed by hydrolysis using hydrochloric acid or glutaminase, glutamine acid and ethylamine were produced in a ratio of 1:1. Thus, since the isolated substance was hydrolyzed by glutaminase, it was shown that ethylamine was gamma-ethylamine of glutamine acid. Furthermore, it was confirmed on the basis of glutamate dehydrogenase that glutamine acid produced by hydrolysis was L-glutamine acid.

References: [1]Patent: EP1743634,2007,A1 .Location in patent: Page/Page column 5.

19
[ 56-85-9 ]
[ 557-66-4 ]
[ 945623-40-5 ]
[ 3081-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With glutaminase; at 30℃; for 22h;pH 11;borate buffer; Enzymatic reaction;	By reacting 0.3M glutamine and 1.5M ethylamine hydrochloride in 0.05M borate buffer (pH 11) at 30°C for 22 hours under the presence of 0.3U glutaminase (commercially available product), 225nmol of theanine were obtained. The reaction solution was then subject to chromatography using Dowex 50 x 8 and Dowex 1 x 2 columns (both made by Muromachi Technos Co. , Ltd.) and to ethanol treatment to isolate the target substance from the reaction solution. 8.5g of theanine were thus obtained. The isolated substance was then subject to an amino acid analyzer (made by Hitachi, Ltd.) and paper chromatography and, by exhibition of the same behavior as a standard substance, was confirmed to be L-theanine. Upon hydrolytic treatment with hydrochloric acid or glutaminase, monosodium glutamate and ethylamine were produced at a ratio of 1:1. That the isolated substance is hydrolyzed by glutaminase indicates that ethylamine is bonded to the gamma position of monosodium glutamate. That the monosodium glutamate resulting from hydrolysis is the L-isomer was confirmed by means of monosodium glutamate dehydrogenase.

References: [1]Patent: EP1743633,2007,A1 .Location in patent: Page/Page column 8-9.

20
[ 75-04-7 ]
[ 138036-14-3 ]
[ 3081-61-6 ]

Yield	Reaction Conditions	Operation in experiment
89%		Example 1: Preparation of N (5) -ethyl-L-glutamine (theanine)5.8 g of N-phthaloyl-L-glutamic acid 5-methyl ester(formula 1: R = Me, Xi = X2 = X3 = X4 = H) was added to 12.9 g of 70% ethylamine solution at 0C and stirred for one hour. Then, the reaction temperature was raised up to20C. After stirring the resulting solution at 20C for 22 hours, the ethylamine existing excessively was removed under reduced pressure. After adding 38.6 g of acetone to the resulting solution, the pH of the solution was regulated as 5 to 6 using acetic acid. Then, the resulting solution was stirred for one hour. Produced solids were filtrated and washed with ethanol . The filtrated white solids were dried to obtain a target compound (3.1 g, 89%).NMR (D2O) delta(ppm) : 3.77(t, IH), 3.20(q, 2H), 2.40(m, 2H), 2.13 (dd, 2H), l.ll(t, 3H) [alpha]20 +8.0 (c=5, H2O)

References: [1]Patent: WO2006/123909,2006,A1 .Location in patent: Page/Page column 15.

21
[ 3081-61-6 ]
[ 7646-85-7 ]
[(L-γ-glutamyl-ethylamide(-1H))2Zn] [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1077 - 1081.

22
[ 75-04-7 ]
[ 142-47-2 ]
[ 3081-61-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,2009,vol. 73,p. 2677 - 2683.

23
[ 3081-61-6 ]
[ 56-86-0 ]
[ 75-04-7 ]

References: [1]Bioscience, Biotechnology and Biochemistry,2010,vol. 74,p. 1936 - 1939.

24
[ 10148-81-9 ]
[ 3081-61-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,2010,vol. 74,p. 1936 - 1939.

25
[ 3081-61-6 ]
[ 69-79-4 ]
[ 1437967-19-5 ]
[ 1437967-23-1 ]