Tricholomic acid

Tricholomic acid
Names
	IUPAC name (2S)-2-Amino-2-[(5S)-3-oxo-1,2-oxazolidin-5-yl]acetic acid
	Other names α-Cycloglutamate; α-Amino-3-oxo-5-isoxazolidineacetic acid
Identifiers
CAS Number	2644-49-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9690;
ChEMBL	ChEMBL260328;
ChemSpider	390188;
KEGG	C08298;
PubChem CID	441456;
CompTox Dashboard (EPA)	DTXSID80949327 ;
	InChI InChI=1S/C5H8N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h2,4H,1,6H2,(H,7,8)(H,9,10)/t2-,4-/m0/s1 Key: NTHMUJMQOXQYBR-OKKQSCSOSA-N;
	SMILES C1[C@H](ONC1=O)[C@@H](C(=O)O)N;
Properties
Chemical formula	C5H8N2O4
Molar mass	160.129 g·mol−1
Melting point	207 °C (405 °F; 480 K) (decomp.)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tricholomic acid is a non-proteinogenic amino acid found in some mushrooms, including Tricholoma muscarium.^[1] It has a chemical structure similar to glutamic acid, hence the synonym cycloglutamate, and it interacts with glutamate receptors.^[2] Because glutamate receptors are thought to be responsible for the reception of umami taste, tricholomic acid and close analogs have been investigated as flavor enhancers.^[3]

References

^ ^a ^b Takemoto, Tsunematsu; Nakajima, Tadashi (1964). "Studies on the Constituents of Indigenous Fungi. I". Yakugaku Zasshi. 84 (12): 1183–1186. doi:10.1248/yakushi1947.84.12_1183. PMID 14266548.
^ Tamborini, Lucia; Mastronardi, Federica; Lo Presti, Leonardo; Nielsen, Birgitte; De Micheli, Carlo; Conti, Paola; Pinto, Andrea (2017). "Synthesis of L-Tricholomic Acid Analogues and Pharmacological Characterization at Ionotropic Glutamate Receptors". ChemistrySelect. 2 (31): 10295. doi:10.1002/slct.201702154. hdl:2434/528800.
^ Kuninaka, Akira (1969). "Recent Studies of 5′-Nucleotides as New Flavor Enhancers". Flavor Chemistry. Advances in Chemistry. 56: 261–274. doi:10.1021/ba-1966-0056.ch015. ISBN 0-8412-0057-2.