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L-2-Aminoadipic acid, also known as α-aminoadipate, is a gliotoxin and a structural analog of glutamine. It is generated by the catabolism of lysine saccharopine (SAC)/pipecolic acid (PIP) pathways and is the L-enantiomer of 2-aminoadipic acid. L-2-Aminoadipic acid is a white solid and serves as an important raw material and intermediate in various industries, including organic synthesis, pharmaceuticals, and agrochemicals.

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  • 1118-90-7 Structure
  • Basic information

    1. Product Name: L-2-Aminoadipic acid
    2. Synonyms: ALPHA-AMINOHEXANDIOIC ACID;AMINOADIPIC ACID, L-2-;AAD;2-AMINO-HEXANEDIOIC ACID;H-L-HOGLU-OH;HOMOGLUTAMIC ACID;H-HOMOGLU-OH;HEXANEDIOIC ACID, 2-AMINO-, (2S)-
    3. CAS NO:1118-90-7
    4. Molecular Formula: C6H11NO4
    5. Molecular Weight: 161.16
    6. EINECS: -0
    7. Product Categories: Amino Acids;Biochemistry;non-Proteinorganic Amino Acids
    8. Mol File: 1118-90-7.mol
  • Chemical Properties

    1. Melting Point: 203-205 °C (dec.)(lit.)
    2. Boiling Point: 287.44°C (rough estimate)
    3. Flash Point: 173.9 °C
    4. Appearance: White/Solid
    5. Density: 1.3482 (rough estimate)
    6. Vapor Pressure: 2.74E-06mmHg at 25°C
    7. Refractive Index: 1.4230 (estimate)
    8. Storage Temp.: Store at RT.
    9. Solubility: N/A
    10. PKA: 2.49±0.24(Predicted)
    11. Water Solubility: Soluble in 1N HCl (50 mg/ml) and water (slightly).
    12. BRN: 1724348
    13. CAS DataBase Reference: L-2-Aminoadipic acid(CAS DataBase Reference)
    14. NIST Chemistry Reference: L-2-Aminoadipic acid(1118-90-7)
    15. EPA Substance Registry System: L-2-Aminoadipic acid(1118-90-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1118-90-7(Hazardous Substances Data)

1118-90-7 Usage

Uses

1. Used in Pharmaceutical Industry:
L-2-Aminoadipic acid is used as an inhibitor of ischemic glutamate release for preventing neuronal damage during ischemic events. It helps in reducing the excitotoxic effects of glutamate, which can lead to cell death in the brain.
2. Used in Organic Synthesis:
L-2-Aminoadipic acid is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the development of new molecules with potential applications in various fields.
3. Used in Agrochemicals:
L-2-Aminoadipic acid is used as a raw material in the production of certain agrochemicals, contributing to the development of new products for agricultural applications.
4. Used in Research and Development:
L-2-Aminoadipic acid is utilized in research and development for studying its properties and potential applications in various industries, including the development of new drugs and chemical compounds.

Biochem/physiol Actions

L-2-Aminoadipic acid inhibits glutamine synthetase and γ-glutamylcysteine synthetase. It modulates glucose metabolism and is present in higher levels in diabetic patients. L-2-Aminoadipic acid plays a key role in suppressing autophagy in C2C12 myotubes.

Check Digit Verification of cas no

The CAS Registry Mumber 1118-90-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,1 and 8 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1118-90:
(6*1)+(5*1)+(4*1)+(3*8)+(2*9)+(1*0)=57
57 % 10 = 7
So 1118-90-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/p-2

1118-90-7 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (A1457)  L-2-Aminoadipic Acid  >98.0%(T)

  • 1118-90-7

  • 1g

  • 990.00CNY

  • Detail
  • TCI America

  • (A1457)  L-2-Aminoadipic Acid  >98.0%(T)

  • 1118-90-7

  • 5g

  • 2,990.00CNY

  • Detail
  • Alfa Aesar

  • (L13924)  L-2-Aminoadipic acid, 98%   

  • 1118-90-7

  • 1g

  • 812.0CNY

  • Detail
  • Alfa Aesar

  • (L13924)  L-2-Aminoadipic acid, 98%   

  • 1118-90-7

  • 5g

  • 2902.0CNY

  • Detail

1118-90-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name L-2-aminoadipic acid

1.2 Other means of identification

Product number -
Other names L-2-AMinoadipic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1118-90-7 SDS

1118-90-7Relevant articles and documents

Hydrolytic cleavage of pyroglutamyl-peptide bond. I. The susceptibility of pyroglutamyl-peptide bond to dilute hydrochloric acid

Hashimoto,Ohki,Sakura

, p. 2068 - 2074 (1995)

The susceptibility of the pyroglutamyl-peptide bond in some biologically active peptides, dog neuromedin U-8 fragment (pGlu-Phe-Leu-Phe-Arg-Pro-Arg- OH), human big gastrin fragment (pGlu-Leu-Gly-Pro-OH) and thyrotropin releasing hormone (TRH) fragments (pGlu-His-Pro-OH, pGlu-His-OH), to 1 N HCl under mild conditions and/or at 60°C was studied. It was found that the N- terminal portion of pGlu-peptides is extremely labile to acid hydrolysis, giving not only the ring-opened product of the pyrrolidone moiety of the pGlu residue, but also the cleavage product of the pGlu-peptide linkage. The ring- opening reaction predominated over the cleavage reaction in hydrolysis of the four peptides in 1 N HCl at 60°C. The ring-opening reaction and the cleavage reaction of pGlu-peptide linkage proceeded faster than the cleavage of internal peptide bonds. The rate of hydrolysis was affected by the reaction temperature, and the ring-opening reaction was greatly diminished at 4°C in comparison with the cleavage reaction. Thus, the phenomenon that the pGlu- peptide bond is susceptible to dilute HCl as compared to the other peptide bonds appears to be a general one.

High Performance Liquid Chromatography (HPLC.) of Natural Products. III . Isolation of New Tripeptides from the Fermentation Broth of P. Chrysogenum

Neuss, N.,Miller, R. D.,Affolder, C. A.,Nakatsukasa, W.,Mabe, J.,et al.

, p. 1119 - 1129 (1980)

α-Aminoadipoyl-alanyl-valine, α-aminoadipoyl-serinyl-valine and α-aminoadipoyl-serinyl-isodehydrovaline have been isolated from the fermentation broth of P. chrysogenum.The configuration of α-aminoadipoyl-serinyl-valine has been shown to be L, L, D.

Preparation method of beta-homoglutamic acid

-

Paragraph 0022; 0031-0032, (2020/11/05)

The invention belongs to the field of preparation of organic compounds, and provides a preparation method of beta-homoglutamic acid. The method is characterized in that: 3-cyclohexenecarboxylic acid is used as a raw material, beta-homoglutamic acid is synthesized at a high yield through three the steps of reactions of Curtius rearrangement, olefin oxidation and protection group removal, and beta-homoglutamic acid with high yield and high optical purity can be obtained through configuration retention by using optically pure 3-cyclohexenecarboxylic acid. The method has the advantages of easily available raw materials, mild reaction conditions and low cost, and is suitable for large-scale preparation of beta-homoglutamic acid.

Colony-wise Analysis of a Theonella swinhoei Marine Sponge with a Yellow Interior Permitted the Isolation of Theonellamide i

Fukuhara, Kazuya,Takada, Kentaro,Watanabe, Ryuichi,Suzuki, Toshiyuki,Okada, Shigeru,Matsunaga, Shigeki

, p. 2595 - 2599 (2018/12/13)

There are several examples of marine organisms whose metabolic profiles differ among conspecifics inhabiting the same region. We have analyzed the metabolic profile of each colony of a Theonella swinhoei marine sponge with a yellow interior and noticed the patchy distribution of one metabolite. This compound was isolated and its structure was studied by a combination of spectrometric analyses and chemical degradation, showing it to be a congener in the theonellamide class of bicyclic peptides. Theonellamides had previously been isolated by us only from T. swinhoei with a white interior and not from those with a yellow interior.

Peculiar stability of amino acids and peptides from a radical perspective

Watts, Zachary I.,Easton, Christopher J.

supporting information; experimental part, p. 11323 - 11325 (2011/03/19)

(Chemical Equation Presented) Photochemical reactions of free and N-acetyl α-amino acids with chlorine and deuterium labeled hydrogen peroxide have been used to determine both the relative rates of reaction of molecules of these classes and the relative reactivity of their different types of hydrogen toward abstraction by chlorine and oxygen centered radicals. The relative rates of reaction of these species range over more than 3 orders of magnitude; however, where data are available from more than one amino acid for a particular type of group at a specific position on the side chain, the values are remarkably similar. The predictive utility of these results has been demonstrated for the regioselective chlorination of tripeptides. More generally this analysis shows that the backbone and adjacent side chain positions of amino acids and peptides are peculiarly resistant to hydrogen atom transfer, and a similar pattern of reactivity has been noted from earlier studies of reactions of modified substrates catalyzed by isopenicillin-N-synthetase. Such resistance stands out in contrast to the common occurrence of free radical reactions of α-amino acids, peptides, and proteins and their importance in biology. Nevertheless, it provides a reason for the ability of amino acids and their derivatives to avoid degradation in Nature where they are constantly exposed to radicals, and it accounts, at least in part, for the anomalous ability of enzymes to catalyze free radical reactions without being broken down by the radical intermediates.

WA8242A1, A2 and B, novel secretary phospholipase A2 inhibitors produced by Streptomyces violaceusniger. III. Structure elucidation and total synthesis of WA8242B

Yoshimura, Seiji,Otsuka, Takanao,Takase, Shigehiro,Okamoto, Masanori,Okada, Satoshi,Hemmi, Keiji

, p. 655 - 664 (2007/10/03)

The structure of WA8242B, a potent novel inhibitor against phospholipase A2, was fully characterized by spectroscopic methods and chemical degradation. The success of total synthesis of WA8242B confirmed the structure and allowed the pharmacological study of WA8242B. The structures of WA8242A1 and A2 were also described.

Enantiocontrolled synthesis of two amino acids; (S)-glutamic acid and (S)-2-aminoadipic acid

Takano,Kamikubo,Moriya,Ogasawara

, p. 601 - 604 (2007/10/02)

An efficient enantiocontrolled route to two acidic amino acids, (S)-glutamic acid and (S)-2-aminoadipic acid, has been developed starting from chiral equivalents of cyclopentadienone and cyclohexadienone, respectively.

Simultaneous Production of D-Pipecolic Acid and L-α-Aminoadipic Acid from DL-Pipecolic Acid Using a Microorganism

Mochizuki, Kazuya,Yamazaki, Yoshimitsu,Maeda, Hidekatsu

, p. 1113 - 1116 (2007/10/02)

The production of D-pipecolic acid from DL-pipecolic acid using a microbe was investigated.Some bacteria which assimilated L-pipecolic acid in preference to D-pipecolic acid and accumulated L-α-aminoadipic acid extracellularly when cultivated on DL-pipecolic acid were isolated.When one of these bacteria, which was designated as Alcaligenes sp. 309B1, was cultivated on a medium containing 5percent of DL-pipecolic acid, it assimilated all of the L-pipecolic acid, with most of the D-pipecolic acid not being assimilated.Ninety-five percent of the D-pipecolic acid remained after the complete disappearance of L-pipecolic acid from the culture broth.The amount of L-α-aminoadipic acid accumulated in the broth reached 56percent of the total quantity of L-pipecolic acid.

Chemical Conversion of L-α,ο-Diamino Acids to L-ο-Carbamoyl-α-amino Acids by Ruthenium tetroxide Oxidation

Yoshifuji, Shigeyuki,Tanaka, Ken-ichi,Nitta, Yoshihiro

, p. 2994 - 3001 (2007/10/02)

Ruthenium tetroxide oxidation of N,C-protected derivatives of L-2,4-diaminobutyric acid, L-ornitine and L-lisine was carried out two-phase conditions and the corresponding imides, formed through the oxidation of the methylene adjacent to the ο-amino group, were obtained in good yields.Removal of the protecting groups from the products gave L-asparagine, L-glutamine and L-2-aminoadipic acid 6-amide, respectively.Thus the first chemical conversion of L-α,ο-diamino acids into the corresponding L-ο-carbamoyl-α-amino acids without racemization has been established.L-2-Aminoadipic acid 6-amide was further converted to L-2-aminoadipic acid by acid hydrolysis.This represents a convenient method for the synthesis of L-2-aminoadipic acid starting from L-lisine.Keywords - oxidation; ruthenium tetroxide; L-α-amino acid synthesis; N-protecting group; ruthenium tetroxide; L-α,ο-diamino acid; L-ο-carbamoiyl-α-amino acid; L-2-aminoadipicacid

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