2,088
edits
Changes
Jump to navigation
Jump to search
Line 1:
Line 1: − {{chembox − | ImageFile = Theanine.png − | ImageFile_Ref = {{chemboximage|correct|??}} − | ImageSize = 160 − | ImageName = Stereo, skeletal formula of theanine (S) − | IUPACName = 2-Amino-4-(ethylcarbamoyl)butyric acid{{citation needed|date=July 2012}} − | OtherNames = ''N''<sup>5</sup>-Ethyl-<small>L</small>-glutamine<ref>{{cite doi|10.1007/BF00231550}}</ref> − | Section1 = {{chembox Identifiers − | CASNo = 3081-61-6 − | CASNo_Ref = {{cascite|correct|??}} − | CASNo_Comment = <small>''S''</small> − | PubChem = 228398 − | PubChem_Ref = {{pubchemcite|correct|pubchem}} − | PubChem1 = 9964226 − | PubChem1_Ref = {{pubchemcite|correct|pubchem}} − | PubChem1_Comment = <small>''R''</small> − | PubChem2 = 439378 − | PubChem2_Ref = {{pubchemcite|correct|pubchem}} − | PubChem2_Comment = <small>''S''</small> − | ChemSpiderID = 198778 − | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} − | ChemSpiderID1 = 8139819 − | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} − | ChemSpiderID1_Comment = <small>''R''</small> − | ChemSpiderID2 = 388498 − | ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} − | ChemSpiderID2_Comment = <small>''S''</small> − | UNII = 8021PR16QO − | UNII_Ref = {{fdacite|correct|FDA}} − | EINECS = 3081-61-6 − | MeSHName = theanine − | ChEBI = 17394 − | ChEBI_Ref = {{ebicite|correct|EBI}} − | SMILES = CC[nH]:c(:[o])CCC(N)c(:[o]):[oH] − | SMILES1 = CCNC(=O)CCC(N)C(O)=O − | StdInChI = 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) − | StdInChI_Ref = {{stdinchicite|correct|chemspider}} − | StdInChIKey = DATAGRPVKZEWHA-UHFFFAOYSA-N − | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} − }} − | Section2 = {{chembox Properties − | C = 7 − | H = 14 − | N = 2 − | O = 3 − }} − | Section3 = {{chembox Related − | Function = alkanoic acids − | OtherFunctn = {{unbulleted list|[[Arginine]]|[[Pantothenic acid]]|[[Hopantenic acid]]}} − | OtherCpds = [[Panthenol]] − }} − }} −
no edit summary
'''Theanine''' ({{IPAc-en|icon|ˈ|θ|iː|ən|iː|n}}), also '''gamma-glutamylethylamide''' or '''5-N-ethyl-glutamine''', is an [[amino acid]] and a [[glutamic acid]] analog commonly found in [[tea]] (infusions of ''[[Camellia sinensis]]''), primarily in [[black tea]],<ref>{{cite journal|url=http://www.sciencedirect.com/science/article/pii/S0308814610011416|title=How much theanine in a cup of tea? Effects of tea type and method of preparation|date=15 March 2011|doi=10.1016/j.foodchem.2010.08.071|last1=Keenan|first1=Emma K.|last2=Finnie|first2=Mike D.A.|last3=Jones|first3=Paul S.|last4=Rogers|first4=Peter J.|last5=Priestley|first5=Caroline M.|journal=Food Chemistry|volume=125|issue=2|pages=588}}</ref> and also in the basidiomycete mushroom ''[[Boletus badius]]'' and in [[ilex guayusa|guayusa]].<ref name="casimir">{{cite journal |author=Casimir J, Jadot J, Renard M |title=[Separation and characterization of N-ethyl-gamma-glutamine from Xerocomus badius.] |journal=Biochim Biophys Acta |volume=39 |pages=462–8 |year=1960 |pmid=13808157 |doi=10.1016/0006-3002(60)90199-2 |issue=3}}</ref> More specifically, this compound is called '''<small>L</small>-theanine''', being the L- amino acid (not to be confused with a [[levorotatory]] [[enantiomer]]). In 1950, the tea laboratory of Kyoto successfully separated theanine from [[gyokuro]] leaf, which has high theanine content.{{citation needed|date=August 2012}} Theanine is an [[Structural analog|analog]] to [[glutamine]] and [[glutamate]], and can cross the [[blood–brain barrier]].<ref name="yokogoshi">{{cite journal |author=Yokogoshi H, Kobayashi M, Mochizuki M, Terashima T |title=Effect of theanine, r-glutamylethylamide, on brain monoamines and striatal dopamine release in conscious rats |journal=Neurochem Res |volume=23 |issue=5 |pages=667–73 |year=1998 |pmid=9566605 |doi=10.1023/A:1022490806093}}</ref> It is sold in the US as a dietary supplement, and is classified by the [[FDA]] as a [[generally recognized as safe]] (GRAS) ingredient.<ref>{{cite web|url=http://www.nutraingredients-usa.com/Industry/FDA-confirms-GRAS-status-of-Suntheanine|title=FDA confirms GRAS status of Suntheanine|date=March 22, 2007|publisher=NutraIngredients-USA.com}}</ref> However, the German Federal Institute for Risk Assessment (Bundesinstitut für Risikobewertung, BfR) has objected to the addition of isolated theanine to beverages.<ref name="BfR"/>
'''Theanine''' ({{IPAc-en|icon|ˈ|θ|iː|ən|iː|n}}), also '''gamma-glutamylethylamide''' or '''5-N-ethyl-glutamine''', is an [[amino acid]] and a [[glutamic acid]] analog commonly found in [[tea]] (infusions of ''[[Camellia sinensis]]''), primarily in [[black tea]],<ref>{{cite journal|url=http://www.sciencedirect.com/science/article/pii/S0308814610011416|title=How much theanine in a cup of tea? Effects of tea type and method of preparation|date=15 March 2011|doi=10.1016/j.foodchem.2010.08.071|last1=Keenan|first1=Emma K.|last2=Finnie|first2=Mike D.A.|last3=Jones|first3=Paul S.|last4=Rogers|first4=Peter J.|last5=Priestley|first5=Caroline M.|journal=Food Chemistry|volume=125|issue=2|pages=588}}</ref> and also in the basidiomycete mushroom ''[[Boletus badius]]'' and in [[ilex guayusa|guayusa]].<ref name="casimir">{{cite journal |author=Casimir J, Jadot J, Renard M |title=[Separation and characterization of N-ethyl-gamma-glutamine from Xerocomus badius.] |journal=Biochim Biophys Acta |volume=39 |pages=462–8 |year=1960 |pmid=13808157 |doi=10.1016/0006-3002(60)90199-2 |issue=3}}</ref> More specifically, this compound is called '''<small>L</small>-theanine''', being the L- amino acid (not to be confused with a [[levorotatory]] [[enantiomer]]). In 1950, the tea laboratory of Kyoto successfully separated theanine from [[gyokuro]] leaf, which has high theanine content.{{citation needed|date=August 2012}} Theanine is an [[Structural analog|analog]] to [[glutamine]] and [[glutamate]], and can cross the [[blood–brain barrier]].<ref name="yokogoshi">{{cite journal |author=Yokogoshi H, Kobayashi M, Mochizuki M, Terashima T |title=Effect of theanine, r-glutamylethylamide, on brain monoamines and striatal dopamine release in conscious rats |journal=Neurochem Res |volume=23 |issue=5 |pages=667–73 |year=1998 |pmid=9566605 |doi=10.1023/A:1022490806093}}</ref> It is sold in the US as a dietary supplement, and is classified by the [[FDA]] as a [[generally recognized as safe]] (GRAS) ingredient.<ref>{{cite web|url=http://www.nutraingredients-usa.com/Industry/FDA-confirms-GRAS-status-of-Suntheanine|title=FDA confirms GRAS status of Suntheanine|date=March 22, 2007|publisher=NutraIngredients-USA.com}}</ref> However, the German Federal Institute for Risk Assessment (Bundesinstitut für Risikobewertung, BfR) has objected to the addition of isolated theanine to beverages.<ref name="BfR"/>