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1-Aminocyclopropanecarboxylic acid

CAS No.
22059-21-8
Chemical Name:
1-Aminocyclopropanecarboxylic acid
Synonyms
1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID;ACC;Ac3c;1-AMinocyclopropane-1-carboxylate;H-ACPC-OH;AMinocyclopropanecarboxylic acid;Cyclopropanecarboxylic acid, 1-amino-;1-AMINO-1-CYCLOPROPANECARBOXYLIC ACID;1-Aminocyclopropane-1-carboxylic acid (ACC);Acpc-OH
CBNumber:
CB6401146
Molecular Formula:
C4H7NO2
Molecular Weight:
101.1
MDL Number:
MFCD00009944
MOL File:
22059-21-8.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-31 15:25:15

1-Aminocyclopropanecarboxylic acid 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)
EWG's Food Scores 1
FDA UNII 3K9EJ633GL
UNSPSC Code 12352209
NACRES NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE dust mask type N95 (US), Eyeshields, Gloves
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
Storage Class 11 - Combustible Solids
REACH Registrations Active
NFPA 704
0
2 0

1-Aminocyclopropanecarboxylic acid price More Price(88)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 149101-M 1-Aminocyclopropane-1-carboxylic Acid - CAS 22059-21-8 - Calbiochem An agonist for the glycine modulatory site of the N-methyl-D-aspartate (NMDA) receptor complex. 22059-21-8 250mg $147 2026-04-30 Buy
Sigma-Aldrich 149101-M 1-Aminocyclopropane-1-carboxylic Acid - CAS 22059-21-8 - Calbiochem An agonist for the glycine modulatory site of the N-methyl-D-aspartate (NMDA) receptor complex. 22059-21-8 1g $342 2026-04-30 Buy
TCI Chemical A1178 1-Aminocyclopropanecarboxylic Acid >97.0%(T) 22059-21-8 1g $76 2026-04-30 Buy
TCI Chemical A1178 1-Aminocyclopropanecarboxylic Acid >97.0%(T) 22059-21-8 5g $178 2026-04-30 Buy
Cayman Chemical 16132 1-Aminocyclopropanecarboxylic Acid ≥98% 22059-21-8 100mg $36 2026-04-30 Buy
Product number Packaging Price Buy
149101-M 250mg $147 Buy
149101-M 1g $342 Buy
A1178 1g $76 Buy
A1178 5g $178 Buy
16132 100mg $36 Buy

1-Aminocyclopropanecarboxylic acid Chemical Properties,Uses,Production

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 a plant growth regulator. It is an NMDA agonist acting at the glycine site.

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.

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.

Production Methods

ACC is produced through an industrial process that typically begins with preparation of a suitably protected amino-acid precursor, followed by a controlled cyclopropanation step that forms the strained three-membered ring while suppressing rearrangements and over-alkylation. Once the cyclopropane framework is established, deprotection and purification steps yield the free amino acid, with downstream operations centred on crystallisation, solvent removal, and multi-stage filtration to meet agrochemical specifications for optical purity, residual solvents, and trace by-products.

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.

Mechanism of action

As an ethylene releasing substance it affects the growth and development of plants as well as their senescence.

References

[1] A B BLEECKER  H K. Ethylene: a gaseous signal molecule in plants.[J]. Annual review of cell and developmental biology, 2000, 16: 1-18. DOI: 10.1146/annurev.cellbio.16.1.1
[2] R NAHUM-LEVY. Putative partial agonist 1-aminocyclopropanecarboxylic acid acts concurrently as a glycine-site agonist and a glutamate-site antagonist at N-methyl-D-aspartate receptors.[J]. Molecular Pharmacology, 1999, 56 6: 1207-1218. DOI: 10.1124/mol.56.6.1207

Pesticide Type

Herbicide; Plant Growth Regulator

68781-13-5
22059-21-8
Synthesis of 1-Aminocyclopropanecarboxylic acid from 1-Aminocyclopropane-1-carboxylic acid hydrochloride
Global( 575)Suppliers
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