Names | |
---|---|
Preferred IUPAC name 5-Methylidenefuran-2(5H)-one | |
Other names 4-Methylenebut-2-en-4-olide | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.003.244 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C5H4O2 | |
Molar mass | 96.08 g/mol |
Appearance | Pale yellow oil |
Boiling point | 73 [2] °C (163 °F; 346 K) |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 190 mg·kg−1 (mouse) [3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Protoanemonin (sometimes called anemonol or ranunculol [4] ) is a toxin found in all plants of the buttercup family (Ranunculaceae). When the plant is wounded or macerated, the unstable glucoside found in the plant, ranunculin, is enzymatically broken down into glucose and the toxic protoanemonin. [5] It is the lactone of 4-hydroxy-2,4-pentadienoic acid.
Contact with a wounded plant causes itch, rashes or blistering on contact with the skin or mucosa. Ingesting the toxin can cause nausea, vomiting, dizziness, spasms, acute hepatitis, jaundice, or paralysis. [6] [7] [8]
When drying the plant, protoanemonin comes into contact with air and dimerizes to anemonin, which is further hydrolyzed to a non-toxic dicarboxylic acid. [5] [9]
ranunculin | |
↓ – glucose | (maceration, enzymatically) |
protoanemonin | |
↓ dimerization | (air or water contact) |
anemonin | |
↓ hydrolyzation | |
4,7-dioxo-2-decenedioic acid |
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.
Phenol, or Benzenol, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.
Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless, bitter-tasting solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.
Ficaria verna, commonly known as lesser celandine or pilewort, is a low-growing, hairless perennial flowering plant in the buttercup family Ranunculaceae native to Europe and Western Asia. It has fleshy dark green, heart-shaped leaves and distinctive flowers with bright yellow, glossy petals. It is now introduced in North America, where it is known by the common name fig buttercup and considered an invasive species. The plant is poisonous if ingested raw and potentially fatal to grazing animals and livestock such as horses, cattle, and sheep. For these reasons, several US states have banned the plant or listed it as a noxious weed. It prefers bare, damp ground and is considered by horticulturalists in the United Kingdom as a persistent garden weed; nevertheless, many specialist plantsmen, nursery owners and discerning gardeners in the UK and Europe collect selected cultivars of the plant, including bronze-leaved and double-flowered ones. Emerging in late winter with flowers appearing late February through May in the UK, its appearance across the landscape is regarded by many as a harbinger of spring.
The nitrite ion has the chemical formula NO−
2. Nitrite is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also refers to organic compounds having the –ONO group, which are esters of nitrous acid.
Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a trimethylated derivative of ammonia. TMA is widely used in industry. At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact. At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish.
Crotonic acid ((2E)-but-2-enoic acid) is a short-chain unsaturated carboxylic acid described by the formula CH3CH=CHCO2H. The name crotonic acid was given because it was erroneously thought to be a saponification product of croton oil. It crystallizes as colorless needles from hot water. With a cis-alkene, Isocrotonic acid is an isomer of crotonic acid. Crotonic acid is soluble in water and many organic solvents. Its odor is similar to that of butyric acid.
Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms, it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used in pharmaceutical and cosmetic products as a moisturizer and to improve wound healing.
Amatoxin is the collective name of a subgroup of at least nine related toxic compounds found in three genera of poisonous mushrooms and one species of the genus Pholiotina. Amatoxins are very potent, as little as half a mushroom cap can cause severe liver injury if swallowed.
A cyanogen halide is a molecule consisting of cyanide and a halogen. Cyanogen halides are chemically classified as pseudohalogens.
Boron triiodide is a chemical compound of boron and iodine with chemical formula BI3. It has a trigonal planar molecular geometry.
In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations.
Toxiferine is a curare toxin. It is a bisindole alkaloid derived from Strychnos toxifera and a nicotinic acetylcholine receptor antagonist. This alkaloid is the main toxic component of Calabash curare, and one of the most toxic plant alkaloids known. The lethal dose (LD50) for mice has been determined as 10 - 60 µg/kg by intravenous administration. It is a muscle relaxant that causes paralysis of skeletal muscle, which takes approximately 2 hours to recovery for a moderate dose, and 8 hours of total paralysis with a 20-fold paralytic dose. The paralysis can be antagonized by neostigmine
Ranunculin is an unstable glucoside found in plants of the buttercup family (Ranunculaceae). On maceration, for example when the plant is wounded, it is enzymatically broken down into glucose and the toxin protoanemonin.
An alkylbenzene is a chemical compound that contains a monocyclic aromatic ring attaching to one or more saturated hydrocarbon chains. Alkylbenzenes are derivatives of benzene, in which one or more hydrogen atoms are replaced by alkyl groups. The simplest member, toluene, has the hydrogen atom of the benzene ring replaced by a methyl group. The chemical formula of alkylbenzenes is CnH2n-6.
Steroidal alkaloids have the basic steroidal skeleton with nitrogen-based functional groups attached to the skeleton. More specifically, they are distinguished by their tetracyclic cyclopentanoperhydrophenanthrene skeleton that marks their close relationship with sterols. They fall in two major categories: Solanum alkaloids and Veratrum alkaloids. A Steroidal alkaloid has also been found in Chonemorpha fragrans, 'chonemorphine' was used to treat intestinal infections in Wistar rats..
2,4,6-Trimethylpyridine (2,4,6-collidine) is an organic compound which belongs to the heterocycles. It consists of a pyridine ring substituted with three methyl groups. It belongs to the substance group of the collidines, a group of six constitutional isomers. 2,4,6-trimethylpyridine is the most well-known isomer of this group.
Quinolizidine alkaloids are natural products that have a quinolizidine structure; this includes the lupine alkaloids.
Luteoskyrin is a carcinogenic mycotoxin with the molecular formula C30H22O12 which is produced by the mold Penicillium islandicum. Luteoskyrin has strong cytotoxic effects. Luteoskyrin can cause the yellow rice disease.
The LD50 of protoanemonin in male Swiss albino mice was 190 mg/kg.