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
cyclopropane-1,1-dicarboxylic acid
IUPAC Name
cyclopropane-1,1-dicarboxylic acid
Canonical 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
Appearance
White crystalline powder.
Storage
Store in a cool, dry place. Store in a tightly closed container. Corrosives area.
Refractive Index
1.5800 (estimate)
LogP
-0.06420

Safety Information

Hazards
H290:
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
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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