Cyclopropane-1,1-dicarboxylic acid
Product Information
Molecular Formula
C5H6O4
Molecular Weight
130.10
Description
Cyclopropane-1,1-dicarboxylic acid (CAS# 598-10-7) is an inhibitor of 1-aminocyclopropane-1-carboxylic Acid oxidase in Lycopersicum esculentum (Tomato plant). It can also be used as a building block for the synthesis of a series of cyclopropanecarboxamides, having antifungal activity.
Synonyms
1,1-Cyclopropanedicarboxylic acid; Vinaconic acid; Cyclopropanedicarboxylic acid; 1-Carboxycyclopropanecarboxylic Acid; Ethylenemalonic Acid; NSC 626865; Vinyl-malonic acid; Propene-3,3-dicarboxylic acid
IUPAC Name
cyclopropane-1,1-dicarboxylic acid
SMILES
C1CC1(C(=O)O)C(=O)O
InChI
InChI=1S/C5H6O4/c6-3(7)5(1-2-5)4(8)9/h1-2H2,(H,6,7)(H,8,9)
InChI Key
FDKLLWKMYAMLIF-UHFFFAOYSA-N
Boiling Point
371.3 °C at 760 mmHg
Melting Point
134-138 °C
Purity
95%
Density
1.708 g/cm3
Solubility
Soluble in Methanol, Water
Appearance
White crystalline powder
Storage
Store at RT
Refractive Index
1.5800 (estimate)
LogP
-0.06420
Related CAS
82353-50-2 (potassium salt)
Safety Information
Hazards
H290:
May be corrosive to metals.
H314:
Causes severe skin burns and eye damage.
May be corrosive to metals.
H314:
Causes severe skin burns and eye damage.
Precautionary Statement
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501
Signal Word
Danger
Computed Properties
XLogP3
-0.2
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Exact Mass
130.02660867 g/mol
Monoisotopic Mass
130.02660867 g/mol
Topological Polar Surface Area
74.6Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
152
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-113980258-A | Antibacterial flame-retardant toughened multifunctional ionomer auxiliary agent and preparation method and application thereof | 2021-11-10 |
| CN-113429954-A | Oil-displacing surfactant system, and preparation method and application thereof | 2021-07-30 |
| CN-113659150-A | Composite dual-functional electrode for eutectic solvent electrolyte flow battery | 2021-07-09 |
| JP-6956911-B1 | Antistatic agent | 2021-06-18 |
| CN-112852471-A | Method for extracting asphalt in oil sand by aid of eutectic solvent | 2021-01-20 |
| CN-112458633-A | Double-component self-crimping high-fluffiness fiber spun-bonded non-woven fabric and preparation method thereof | 2020-12-07 |
| US-2022062142-A1 | Hair lightening compositions providing damage protection and sensorial benefits and methods of use | 2020-08-26 |
| WO-2022047081-A1 | Hair lightening compositions providing damage protection and sensorial benefits and methods of use | 2020-08-26 |
| WO-2022040555-A2 | Method of treating cancer | 2020-08-21 |
| CN-111925262-A | Preparation method of multi-component low-eutectic liquid based on metal chloride | 2020-08-19 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22812906 | 2012-08-13 | Metal-chelating polymers by anionic ring-opening polymerization and their use in quantitative mass cytometry | Biomacromolecules |
| 22747000 | 2012-07-31 | Self-assembly of amphiphilic liquid crystal polymers obtained from a cyclopropane-1,1-dicarboxylate bearing a cholesteryl mesogen | Langmuir : the ACS journal of surfaces and colloids |
| 21696643 | 2011-06-23 | Protocol: An updated integrated methodology for analysis of metabolites and enzyme activities of ethylene biosynthesis | Plant methods |
| 20944243 | 2010-10-01 | Binding of flexible and constrained ligands to the Grb2 SH2 domain: structural effects of ligand preorganization | Acta crystallographica. Section D, Biological crystallography |
| 19894700 | 2009-12-04 | trans-Directing ability of the amide group: enabling the enantiocontrol in the synthesis of 1,1-dicarboxy cyclopropanes. Reaction development, scope, and synthetic applications | The Journal of organic chemistry |
| 18616259 | 2008-08-21 | Expedient synthesis of pyrrolo[1,2-a]indoles: preparation of the core of yuremamine | Organic letters |
| 18247549 | 2008-02-27 | Discovery of novel hydroxamates as highly potent tumor necrosis factor-alpha converting enzyme inhibitors: Part I--discovery of two binding modes | Journal of medicinal chemistry |
| 16391772 | 2006-01-21 | Scandium triflate catalyzed cycloaddition of imines with 1,1-cyclopropanediesters: efficient and diastereoselective synthesis of multi-substituted pyrrolidines | Organic & biomolecular chemistry |
| 18007381 | 2005-09-30 | Synthesis of thiadiazoles and 1,2,4-triazoles derived from cyclopropane dicarboxylic acid | Molecules (Basel, Switzerland) |
| 14667060 | 2003-11-01 | The simultaneous determination of 1-aminocyclopropane-1-carboxylic acid and cyclopropane-1,1-dicarboxylic acid in Lycopersicum esculentum by high-performance liquid chromatography--electrospray tandem mass spectrometry | Phytochemical analysis : PCA |
