Butenolide
Encyclopedia
Butenolides are a class of lactone
s with a four-carbon
heterocyclic ring structure. They are sometimes considered oxidized
derivatives of furan
. The simplest butenolide is 2-furanone
, which is a common component of larger natural product
s and is sometimes referred to as simply "butenolide". A common biochemically
important butenolide is ascorbic acid
(vitamin C). Butenolide derivatives known as karrikin
s are produced by some plants on exposure to high temperatures due to brush fires. In particular, 3-methyl-2H-furo[2,3-c]pyran-2-one was found to trigger seed germination
in plants whose reproduction is fire-dependent.
Lactone
In chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...
s with a four-carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
heterocyclic ring structure. They are sometimes considered oxidized
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....
derivatives of furan
Furan
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as furans....
. The simplest butenolide is 2-furanone
2-Furanone
2-Furanone is a heterocyclic organic compound. Classified as a lactone, this colourless liquid is a common natural products synthesized by biochemical pathways, especially plants of the genus Angelica, hence its name β-angelica lactone...
, which is a common component of larger natural product
Natural product
A natural product is a chemical compound or substance produced by a living organism - found in nature that usually has a pharmacological or biological activity for use in pharmaceutical drug discovery and drug design...
s and is sometimes referred to as simply "butenolide". A common biochemically
Biochemistry
Biochemistry, sometimes called biological chemistry, is the study of chemical processes in living organisms, including, but not limited to, living matter. Biochemistry governs all living organisms and living processes...
important butenolide is ascorbic acid
Ascorbic acid
Ascorbic acid is a naturally occurring organic compound with antioxidant properties. It is a white solid, but impure samples can appear yellowish. It dissolves well in water to give mildly acidic solutions. Ascorbic acid is one form of vitamin C. The name is derived from a- and scorbutus , the...
(vitamin C). Butenolide derivatives known as karrikin
Karrikin
Karrikins are a group of plant growth regulators found in the smoke of burning plant material. For many years scientists have known that smoke from forest fires had the ability to stimulate the germination of seeds. In 2004, after studying the thousands of chemical compounds found in smoke, it...
s are produced by some plants on exposure to high temperatures due to brush fires. In particular, 3-methyl-2H-furo[2,3-c]pyran-2-one was found to trigger seed germination
Germination
Germination is the process in which a plant or fungus emerges from a seed or spore, respectively, and begins growth. The most common example of germination is the sprouting of a seedling from a seed of an angiosperm or gymnosperm. However the growth of a sporeling from a spore, for example the...
in plants whose reproduction is fire-dependent.