cis-4-Aminocrotonic acid

Base Information

• Chemical Name: cis-4-Aminocrotonic acid
• CAS No.: 55199-25-2
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.105
• UNII: 2B75NX3MA8
• DSSTox Substance ID: DTXSID101017433
• Nikkaji Number: J566.978B
• Wikipedia: (Z)-4-Amino-2-butenoic_acid
• Wikidata: Q4544931
• Pharos Ligand ID: 1S2ZL4BVUF1R
• ChEMBL ID: CHEMBL32307
• Mol file: 55199-25-2.mol

Synonyms:4-aminocrotonic acid;4-aminocrotonic acid, E;4-aminocrotonic acid, Z;cis-4-aminocrotonic acid;trans-4-aminocrotonic acid

Chemical Property of cis-4-Aminocrotonic acid

Chemical Property:

• PSA: 63.32000
• LogP: 0.28620
• Solubility.: H2O: 124 mg/mL
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 101.047678466
• Heavy Atom Count: 7
• Complexity: 87.7

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C=CC(=O)O)N
• Isomeric SMILES: C(/C=C\C(=O)O)N
• Uses: cis-4-Aminocrotonic acid has been used to study its effect on the spontaneous contractions and muscular relaxation of the longitudinal smooth muscle in mouse duodenum. It has also been used as a γ-aminobutyric acid C (GABAC) receptor agonist to study its effect on radial neuronal migration.

Technology Process of cis-4-Aminocrotonic acid

There total 4 articles about cis-4-Aminocrotonic 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: 51.0%

(E)-4-amino-3-bromobut-2-enoic acid (75707-11-8) → (Z)-4-aminobut-2-enoic acid (55199-25-2)

Guidance literature:

With zinc; In water; acetic acid; for 0.5h; Ambient temperature;

DOI:10.1071/CH9801115

Reference yield: 37.0%

(Z)-4-phthalimidocrotonic acid (16011-10-2) → (Z)-4-aminobut-2-enoic acid (55199-25-2)

Guidance literature:

With ethylamine; In ethanol; for 18h; Ambient temperature;

DOI:10.1071/CH9851647

Reference yield:

(E)-4-amino-3-chlorobut-2-enoic acid (75707-12-9) → (Z)-4-aminobut-2-enoic acid (55199-25-2) + 4-amino-n-butyric acid (56-12-2)

Guidance literature:

With sodium hydroxide; sodium amalgam; for 0.75h; Yield given;

DOI:10.1071/CH9801115

upstream raw materials:

(E)-4-amino-3-chlorobut-2-enoic acid

(E)-4-amino-3-bromobut-2-enoic acid

(Z)-4-phthalimidocrotonic acid

Refernces

• 1、 Allan,Johnston,Twitchin. "Synthesis of analogues of GABA. V. Trans and cis isomers of some 4-amino-3-halogenobut-2-enoic acids". . p. 1115 - 1122. Retrieved 2007/10/02.