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HomeProduct name list1-Aminocyclopropanecarboxylic acid

1-Aminocyclopropanecarboxylic acid

Synonym(s):1-Aminocyclopropane-1-carboxylic Acid - CAS 22059-21-8 - Calbiochem;ACPC

  • CAS NO.:22059-21-8
  • Empirical Formula: C4H7NO2
  • Molecular Weight: 101.1
  • MDL number: MFCD00009944
  • EINECS: 606-917-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-25 16:21:11
1-Aminocyclopropanecarboxylic acid Structural

What is 1-Aminocyclopropanecarboxylic acid?

Description

1-Aminocyclopropanecarboxylic acid (ACPC) is an intermediate in the synthesis of ethylene, the plant hormone responsible for biological processes ranging from seed germination to organ senescence. ACPC has been shown to modulate NMDA receptor activity by acting as a partial agonist at the glycine-binding site on NMDA receptors (EC50 = 0.7-0.9 μM) in the presence of low levels (1 μM) of glutamate and as a competitive antagonist at the glutamate-binding site on NMDA receptors (EC50 = 81.6 nM) with high levels (10 μM) of glutamate. This compound has been reported to protect against neuron cell death in in vivo models of ischemia by enabling moderate levels of NMDA receptor activation and attenuating any excess NMDA receptor signaling that may lead to neurotoxicity.

Chemical properties

Crystalline

The Uses of 1-Aminocyclopropanecarboxylic acid

1-Aminocyclopropane-1-carboxylic Acid is a plant growth regulator. It is an NMDA agonist acting at the glycine site.

The Uses of 1-Aminocyclopropanecarboxylic acid

1-Aminocyclopropane-1-carboxylic Acid is an intermediate in the conversion of methionine to ethylene during the ripening in apples. It also plays an important role in the biosynthesis of the plant hormone ethylene.1-Aminocyclopropane-1-carboxylic Acid is shown to block convulsions and death produced by NMDA exposure, significantly reducing seizure induction and cell death of NMDA-treated hippocampal neurons. 1-Aminocyclopropane-1-carboxylic Acid is produced endogenously in the tomato and other higher plants as a product of the action of 1-aminocyclopropane-1-carboxylic acid synthase in the biosynthesis of ethylene.

What are the applications of Application

1-Aminocyclopropane-1-carboxylic Acid is an agonist at the NMDA receptor glycine modulatory site

Definition

ChEBI: A non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position.

Synthesis Reference(s)

Synthetic Communications, 18, p. 141, 1988 DOI: 10.1080/00397918808077338
Synthesis, p. 127, 1984

General Description

1-Aminocyclopropanecarboxylic acid is a member of 1-aminocycloalkanecarboxylic acids.

Biochem/physiol Actions

1-Aminocyclopropanecarboxylic acid (ACC) exhibits anticonvulsant, anxiolytic, anti-addictive, neuroprotective and antidepressant-like effects in rats and mice. ACC does not affect memory or learning processes.

Properties of 1-Aminocyclopropanecarboxylic acid

Melting point: 229-231 °C (lit.)
Boiling point: 189.47°C (rough estimate)
Density  1.2245 (rough estimate)
refractive index  1.4340 (estimate)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  DMSO (Slightly), Water (Slightly)
form  Powder and Granules
pka 2.29±0.20(Predicted)
color  White to off-white
Water Solubility  Soluble in water.
BRN  2076413
Stability: Store in freezer at -20°C
InChI InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)
CAS DataBase Reference 22059-21-8(CAS DataBase Reference)

Safety information for 1-Aminocyclopropanecarboxylic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for 1-Aminocyclopropanecarboxylic acid

InChIKey PAJPWUMXBYXFCZ-UHFFFAOYSA-N
SMILES C1(N)(C(O)=O)CC1

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