1-Aminocyclopropanecarboxylic acid Chemical Properties

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)

InChIKey

PAJPWUMXBYXFCZ-UHFFFAOYSA-N

SMILES

C1(N)(C(O)=O)CC1

CAS DataBase Reference

22059-21-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

GZ1110000

Hazard Note 

Irritant

HS Code 

29213000

MSDS

• Language:English Provider:1-Amino-1-cyclopropanecarboxylic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1-Aminocyclopropanecarboxylic acid Usage And Synthesis

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

Uses

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.

Uses

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

Definition

ChEBI: 1-aminocyclopropanecarboxylic acid is a non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position. It has a role as a plant metabolite and a member of ethylene releasers. It is a monocarboxylic acid and a non-proteinogenic alpha-amino acid. It is functionally related to a cyclopropanecarboxylic acid. It is a conjugate acid of a 1-aminocyclopropanecarboxylate. It is a tautomer of a 1-aminocyclopropanecarboxylic acid zwitterion.

Application

1-aminocyclopropanecarboxylic acid (ACC) is used in the following ways:
(1) Organic synthesis. It is used for the preparation of vinyls and for the formation of imine compounds by decarboxylation with triketones.
(2) Used as a substrate for the determination of ACC deaminase activity for the study of the growth-promoting effects of endophytic isolates obtained from fern roots and cucurbit seeds.
(3) Used as an ethylene precursor to study the effect of high ethylene concentration on lateral root density (LRD) in sorghum brown midrib (bmr) mutants.
(4) Used to study the effect of glycine on the antidepressant and anxiolytic effects of ACC in rats.

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.

1-Aminocyclopropanecarboxylic acid(22059-21-8)Related Product Information

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