L-2-Aminoadipic acid

Base Information

• Chemical Name: L-2-Aminoadipic acid
• CAS No.: 1118-90-7
• Molecular Formula: C6H11NO4
• Molecular Weight: 161.158
• Hs Code.: 29224999
• European Community (EC) Number: 601-134-8
• UNII: 88ZH74L7SR
• DSSTox Substance ID: DTXSID801017096
• Nikkaji Number: J35.842H
• Wikidata: Q27104392
• Metabolomics Workbench ID: 52179
• ChEMBL ID: CHEMBL88804
• Mol file: 1118-90-7.mol

Synonyms:L-2-Aminoadipic acid;1118-90-7;(S)-2-aminohexanedioic acid;(2S)-2-aminohexanedioic acid;L-alpha-Aminoadipic acid;L-alpha-Aminoadipate;L-2-Aminoadipate;h-aad-oh;(S)-2-Aminoadipic acid;L-2-Aminohexanedioate;hexanedioic acid, 2-amino-, (2S)-;l-2-amino adipic acid;homoglutamic acid;2-Aminoadipic acid, L-;Aminoadipate;alpha-Aminoadipate, L-;Hexanedioic acid, 2-amino-, (S)-;MFCD00002636;L-alpha-Aminoadipatic acid;UNII-88ZH74L7SR;CHEMBL88804;88ZH74L7SR;CHEBI:37023;L-aminoadipic acid;L-Homoglutamic acid;a-Aminoadipic acid;Adipic acid, 2-amino-;l-a-aminoadipic acid;h-l-2-aad-oh;L-.alpha.-Aminoadipic acid;a-Aminoadipate;DL-a-Aminoadipate;UN1;DL-2-Aminoadipate;h-2-aad-oh;DL-a-Aminoadipic acid;l-a-aminohexanoic acid;(S)-Aminoadipic Acid;DL-2-Aminohexanedioate;alpha-Amino-adipic acid;L-2-amino-adipic acid;ALHA-AMINOADIPATE;(S)-2-Aminoadipicacid;aminoadipic acid, l-2-;L -alpha-aminoadipic acid;(+/-)-2-Aminoadipate;L-2-Aminohexanedioic acid;(2S)-2-aminoadipic acid;L- alpha -Aminoadipic acid;l-alpha-aminohexanedioic acid;Lopac0_000091;SCHEMBL97323;(S)-2-amino-hexanedioic acid;L-.ALPHA.-AMINOADIPATE;(2S)-2-Amino-hexanedioic Acid;DTXSID801017096;HMS3260C04;Tox21_500091;BDBM50052553;AKOS015920301;CCG-204186;CS-W014381;LP00091;SDCCGSBI-0050079.P002;HEXANEDIOIC ACID, 2-AMINO-, L-;L-2-Aminoadipic acid, >=98% (TLC);NCGC00093593-01;NCGC00093593-02;NCGC00093593-03;NCGC00093593-04;NCGC00260776-01;AS-13597;EU-0100091;EN300-97272;A 7275;C00956;SR-01000075684;J-002657;SR-01000075684-1;Q27104392;Aad;(S)-2-Aminohexanedioic acid;9EF7020B-8995-4D0E-BE44-34D8F18766DF;L--Aminoadipic acid;H-Homoglu-OH;DL--Aminoadipic acid;(RS)-2-Aminohexanedioic acid;H-DL-Homoglu-OH

Chemical Property of L-2-Aminoadipic acid

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 2.74E-06mmHg at 25°C
• Melting Point: 203-205 °C (dec.)(lit.)
• Refractive Index: 1.4230 (estimate)
• Boiling Point: 364 °C at 760 mmHg
• PKA: 2.49±0.24(Predicted)
• Flash Point: 173.9 °C
• PSA: 100.62000
• Density: 1.333 g/cm³
• LogP: 0.35350
• Storage Temp.: Store at RT.
• Water Solubility.: Soluble in 1N HCl (50 mg/ml) and water (slightly).
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 161.06880783
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

98% ^*data from raw suppliers

L-a-Aminoadipic Acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(C(=O)O)N)CC(=O)O
• Isomeric SMILES: C(C[C@@H](C(=O)O)N)CC(=O)O
• Uses: An inhibitor of ischemic glutamate release L-2-Aminoadipic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Technology Process of L-2-Aminoadipic acid

There total 52 articles about L-2-Aminoadipic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(S)-2-(N-benzyl-N-benzyloxycarbonyl)aminoadipic acid (159947-36-1) → L-homoglutamic acid (1118-90-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In water; acetic acid; for 43h; Ambient temperature;

DOI:10.1055/s-1994-25531

Reference yield: 84.0%

cis-1,2-cyclohexanedimethanol (15753-50-1,25712-33-8) → L-homoglutamic acid (1118-90-7) + (3aR,7aS)-hexahydroisobenzofuran-1-one (89395-29-9)

Guidance literature:

With ammonium hydroxide; 2-ketoadipate monosodium salt; In hexane; for 96h; Ambient temperature; enzymatic reaction: (glutamate dehydrogenase (GluDH), horse liver alcohol dehydrogenase (HLADH), triphosphopyridine nucleotide sodium salt (NAD));

DOI:10.1021/jo00362a045

Reference yield: 83.0%

(2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid (24325-14-2) → L-homoglutamic acid (1118-90-7)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; for 2h;

DOI:10.1021/jm00159a015

upstream raw materials:

L-lysine

L-2-aminoadipamic acid

(+/-)-2-chloroacetaminohexanedioic acid

methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate

Downstream raw materials:

1,5-pentanedioic acid

2-oxohexanedioic acid

(L-α-amino-δ-adipyl)-L-cysteinyl-D-valine

L-pyro-2-aminoadipic acid pentafluorophenyl ester

Refernces

• 1、 Kubota,Gaskin,Yang. "Helix-coli transition of poly- -benzyl-L- -aminoadipate and poly-L- -aminoadipic acid in solution.". . p. 4328 - 4337. Retrieved 1972.
• 2、 Greenstein et al.. "-". . p. 1994. Retrieved 1953.
• 3、 Pham,Lubell. "A practical enantioselective synthesis of α-amino dicarboxylates. Preparation of D- and L-α-aminoadipate, α-aminopimelate, and α-aminosuberate". . p. 3676 - 3680. Retrieved 1994.
• 4、 Ramsamy, K.,Olsen, Richard K.,Emery, Thomas. "Synthesis of N-t-Boc-L-α-aminoadipic Acid 1-t-Butyl-6-Ethyl Ester from L-Aspartic Acid: A New Route to L-α-Aminoadipic Acid". . p. 42 - 43. Retrieved 1982.
• 5、 -. "Preparation method of beta-homoglutamic acid". Paragraph 0022; 0031-0032. . Retrieved 2020/11/05.
• 6、 Watts, Zachary I.,Easton, Christopher J.. "Peculiar stability of amino acids and peptides from a radical perspective". supporting information; experimental part. p. 11323 - 11325. Retrieved 2011/03/19.