1-Aminocyclopropane-1-carboxylic acid
Basic information
- CAS
22059-21-8- Standard SMILES
NC1(C(=O)O)CC1- InChIKey
PAJPWUMXBYXFCZ-UHFFFAOYSA-N- Molecular formula
- C4H7NO2
- Average molar mass
- 101.1 g/mol
- Monoisotopic mass
- 101.04767847
Overview
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 member of ethylene releasers and a plant metabolite. 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.
Names & identifiers
- Preferred name
- 1-Aminocyclopropane-1-carboxylic acid
- IUPAC
- 1-aminocyclopropane-1-carboxylic acid
- English name
- 1-Aminocyclopropanecarboxylic acid
- Molecular formula
- C4H7NO2
- Molecular weight
- 101.1
Names & synonyms
1-Aminocyclopropanecarboxylic acid22059-21-81-Aminocyclopropane-1-carboxylic acidCyclopropanecarboxylic acid, 1-amino-ACC acidalpha-Aminocyclopropane carboxylic acid1-aminocyclopropane-1-carboxylate1-Aminocyclopropane carboxylic acid3K9EJ633GLNSC-98430DTXSID9039577CHEBI:18053
Show more names
ACCAc3cH-ACPC-OHAMinocyclopropanecarboxylic acid1-Aminocyclopropane-1-carboxylic acid (ACC)Acpc-OH
RefChem:429423DTXCID7019577606-917-81-azaniumylcyclopropane-1-carboxylateacpcMFCD000099441-Amino-1-cyclopropanecarboxylic acid1-Amino-1-carboxycyclopropane
Database identifiers
- CAS
22059-21-8- PubChem CID
- 535
- DTXSID
DTXSID9039577
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 63.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 106
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Pesticides
Other Treatment
Active substance -> EU Pesticides database: Pending
LogP-2.78
Melting Point229 - 231 °C
Physical DescriptionSolid
Dissociation Constants2.73
Collision Cross Section135.6 Ų [M-H]-
Physicochemical properties
- Melting point
- 229 · 229-231 °C (lit.)
- Boiling point
- 189.47 °C · 189.47°C (rough estimate)
- Density
- 1.2245 · 1.2245 (rough estimate)
- refractive index
- 1.434 · 1.4340 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: 1-aminocyclopropane-1-carboxylic acid (EC: 606-917-8)
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- GZ1110000
- hs_code
- 29213000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
Cellular LocationsCytoplasm
Applications
Description1-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.
Uses1-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.
Uses1-Aminocyclopropane-1-carboxylic Acid is a plant growth regulator. It is an NMDA agonist acting at the glycine site.
General Description1-Aminocyclopropanecarboxylic acid is a member of 1-aminocycloalkanecarboxylic acids.
Related reactions
87 records
Compound notes
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