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Sigma-Aldrich

Cyclopropane-1,1-dicarboxylic acid

97%

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About This Item

Linear Formula:
C3H4(CO2H)2
CAS Number:
Molecular Weight:
130.10
Beilstein/REAXYS Number:
1864823
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

134-136 °C (lit.)

solubility

methanol: soluble 1 g/10 mL, clear, colorless

SMILES string

OC(=O)C1(CC1)C(O)=O

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

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General description

Cyclopropane-1,1-dicarboxylic acid is a dicarboxylic acid. Cyclopropane-1,1-dicarboxylic acid, an inhibitor of 1-aminocyclopropane-1-carboxylic acid oxidase, was quantitated in Lycopersicum esculentum by HPLC-electrospray tandem mass spectrometry. Crystal and molecular structure of cyclopropane-1,1-dicarboxylic acid has been reported.

Application

Cyclopropane-1,1-dicarboxylic acid was used in the preparation of new heterocyclic derivatives of cyclopropane dicarboxylic acid containing thiadiazole and 1,2,4-triazole moieties. It was also used to prepare spiro-cyclopropyl metallocycles.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

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The crystal and molecular structure of cyclopropane-1, 1-dicarboxylic acid.
Meester MAM, et al.
Acta Crystallographica Section B, Structural Science, 27(3), 630-634 (1971)
Tetrahedron, 45, 1219-1219 (1989)
Nora A Foroud et al.
Phytopathology, 109(5), 796-803 (2018-12-13)
Plant signaling hormones such as ethylene have been shown to affect the host response to various pathogens. Often, the resistance responses to necrotrophic fungi are mediated through synergistic interactions of ethylene (ET) with the jasmonate signaling pathway. On the other
Paolo Ingallinella et al.
Biochemistry, 41(17), 5483-5492 (2002-04-24)
Serine proteases are the most studied class of proteolytic enzymes and a primary target for drug discovery. Despite the large number of inhibitors developed so far, very few make contact with the prime site of the enzyme, which constitutes an
Y H Dong et al.
Science in China. Series B, Chemistry, life sciences & earth sciences, 33(11), 1297-1303 (1990-11-01)
The crystal structures of [Pt(NH3)2CPrDCA].H2O (I), [Pt(CH3NH2)2CPrDCA] (II), and [Pt(dmbn) CPrDCA].2.5H2O (III) (where CPrDCA is 1,1-cyclopropanedicarboxylate; dmbn is 2,3-dimethyl-2,3-butyldiamine) are determined. Compound I crystallizes in the orthorhombic space group Pnma with the cell dimensions: a = 6.517(2), b = 9.709(3)

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