Names | |
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Preferred IUPAC name 4-(4-Hydroxy-3-methoxyphenyl)butan-2-one | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.136 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C11H14O3 | |
Molar mass | 194.22 g/mol |
Melting point | 40 to 41 °C (104 to 106 °F; 313 to 314 K) |
Boiling point | 187 to 188 °C (369 to 370 °F; 460 to 461 K) at 14 mmHg |
Insoluble | |
Solubility | Miscible in ether |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Zingerone, also called vanillylacetone, is a major flavor component of ginger, providing the sweet flavor of cooked ginger. [1] Zingerone is a crystalline solid that is sparingly soluble in water and soluble in ether.
Zingerone is similar in chemical structure to other flavor chemicals such as vanillin and eugenol. It is used as a flavor additive in spice oils and in perfumery to introduce spicy aromas.
Fresh ginger does not contain zingerone, but it is produced by cooking or drying of the ginger root, which causes a reverse aldol reaction on gingerol.
Zingerone was first isolated from the ginger root in 1917 by Hiroshi Nomura, a chemistry professor at Tokyo Imperial University. [2] Nomura named the compound and identified the empirical formula of zingerone in his studies at the laboratory of the Agricultural College. He initially identified it as the chemical component contributing pungency to ginger, something further work has disproven. [3]
Nomura identified and later patented a method for the synthesis of zingerone, in which vanillin and acetone are reacted under basic conditions to form dehydrozingerone. This compound is obtained in about 95% quantity. [4] This reaction is followed by catalytic hydrogenation of the intermediate compound in order to form zingerone, obtained in approximately 100% quantity. [5]
This section needs more reliable medical references for verification or relies too heavily on primary sources .(November 2019) |
Ginger compounds have been shown to be active against enterotoxigenic Escherichia coli heat-labile enterotoxin-induced diarrhea. This type of diarrhea is the leading cause of infant death in developing countries. Zingerone is likely the active constituent responsible for the antidiarrheal efficacy of ginger. [6]
Zingerone is recognized as being a particularly efficient free radical scavenger. It is able to scavenge and degrade free radicals and reactive oxygen species in the body, and inhibits enzymes involved in the generation of these reactive oxygen species. [7]
It is used by some flowers to attract pollinating fruit flies by mimicking the sex pheromone of the fly. [8] [9]
A pollinator is an animal that moves pollen from the male anther of a flower to the female stigma of a flower. This helps to bring about fertilization of the ovules in the flower by the male gametes from the pollen grains.
Bulbophyllum is a genus of mostly epiphytic and lithophytic orchids in the family Orchidaceae. It is the largest genus in the orchid family and one of the largest genera of flowering plants with more than 2,000 species, exceeded in number only by Astragalus. These orchids are found in diverse habitats throughout most of the warmer parts of the world including Africa, southern Asia, Latin America, the West Indies, and various islands in the Indian and Pacific Oceans. Orchids in this genus have thread-like or fibrous roots that creep over the surface of trees or rocks or hang from branches. The stem is divided into a rhizome and a pseudobulb, a feature that distinguished this genus from Dendrobium. There is usually only a single leaf at the top of the pseudobulb and from one to many flowers are arranged along an unbranched flowering stem that arises from the base of the pseudobulb. Several attempts have been made to separate Bulbophyllum into smaller genera, but most have not been accepted by the World Checklist of Selected Plant Families.
Cinnamaldehyde is an organic compound with the formula or C₆H₅CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. It is an essential oil. The bark of cinnamon tree contains high concentrations of cinnamaldehyde.
Enterotoxigenic Escherichia coli (ETEC) is a type of Escherichia coli and one of the leading bacterial causes of diarrhea in the developing world, as well as the most common cause of travelers' diarrhea. Insufficient data exists, but conservative estimates suggest that each year, about 157,000 deaths occur, mostly in children, from ETEC. A number of pathogenic isolates are termed ETEC, but the main hallmarks of this type of bacterium are expression of one or more enterotoxins and presence of fimbriae used for attachment to host intestinal cells. The bacterium was identified by the Bradley Sack lab in Kolkata in 1968.
A semiochemical, from the Greek σημεῖον (semeion), meaning "signal", is a chemical substance or mixture released by an organism that affects the behaviors of other individuals. Semiochemical communication can be divided into two broad classes: communication between individuals of the same species (intraspecific) or communication between different species (interspecific).
Interspecies communication is communication between different species of animals, plants, or microorganisms. Although researchers have explored the topic for many years, only recently has interspecies communication been recognized as an established field of inquiry.
GM1 (monosialotetrahexosylganglioside) the "prototype" ganglioside, is a member of the ganglio series of gangliosides which contain one sialic acid residue. GM1 has important physiological properties and impacts neuronal plasticity and repair mechanisms, and the release of neurotrophins in the brain. Besides its function in the physiology of the brain, GM1 acts as the site of binding for both cholera toxin and E. coli heat-labile enterotoxin.
Bactrocera dorsalis, previously known as Dacus dorsalis and commonly referred to as the oriental fruit fly, is a species of tephritid fruit fly that is endemic to Southeast Asia. It is one of the major pest species in the genus Bactrocera with a broad host range of cultivated and wild fruits. Male B. dorsalis respond strongly to methyl eugenol, which is used to monitor and estimate populations, as well as to annihilate males as a form of pest control. They are also important pollinators and visitors of wild orchids, Bulbophyllum cheiri and Bulbophyllum vinaceum in Southeast Asia, which lure the flies using methyl eugenol.
The AB5 toxins are six-component protein complexes secreted by certain pathogenic bacteria known to cause human diseases such as cholera, dysentery, and hemolytic–uremic syndrome. One component is known as the A subunit, and the remaining five components are B subunits. All of these toxins share a similar structure and mechanism for entering targeted host cells. The B subunit is responsible for binding to receptors to open up a pathway for the A subunit to enter the cell. The A subunit is then able to use its catalytic machinery to take over the host cell's regular functions.
Raspberry ketone is a naturally occurring phenolic compound that is the primary aroma compound of red raspberries.
Shogaols are pungent constituents of ginger similar in chemical structure to gingerol. The most common of the group is [6]-shogaol. Like zingerone, it is produced when ginger is dried or cooked. Moreover, shogaol are converted to other constituents when heat is applied over time, which is why ginger loses its spiciness as it is cooked.
Bactrocera cucurbitae, the melon fly, is a fruit fly of the family Tephritidae. It is a serious agricultural pest, particularly in Hawaii.
Bulbophyllum baileyi, commonly known as the fruit fly orchid, is a species of epiphytic or lithophytic orchid that is native to Queensland and New Guinea. It has coarse, creeping rhizomes, curved, yellowish pseudobulbs with a single thick, fleshy leaf, and a single cream-coloured flower with yellow, red or purple spots. It grows on trees and rocks in open forest, often in exposed places.
Methyl eugenol (allylveratrol) is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and is important to insect behavior and pollination. It is found in various essential oils.
In molecular biology, the heat-labile enterotoxin family includes Escherichia coli heat-labile enterotoxin and cholera toxin (Ctx) secreted by Vibrio cholerae.
Triacetic acid lactone is an organic compound derived enzymatically from glucose. It is a light yellow solid that is soluble in organic solvents.
Enteroaggregative Escherichia coli are a pathotype of Escherichia coli which cause acute and chronic diarrhea in both the developed and developing world. They may also cause urinary tract infections. EAEC are defined by their "stacked-brick" pattern of adhesion to the human laryngeal epithelial cell line HEp-2. The pathogenesis of EAEC involves the aggregation of and adherence of the bacteria to the intestinal mucosa, where they elaborate enterotoxins and cytotoxins that damage host cells and induce inflammation that results in diarrhea.
An attractant is any chemical that attracts an organism, e.g. i) synthetic lures; ii) aggregation and sex pheromones ; and iii) synomone
Bactrocera carambolae, also known as the carambola fruit fly, is a fruit fly species in the family Tephritidae, and is native to Asia. This species was described by Drew and Hancock in 1994.
The pollination of orchids is a complex chapter in the biology of this family of plants that are distinguished by the complexity of their flowers and by intricate ecological interactions with their pollinator agents. It has captured the attention of numerous scientists over time, including Charles Darwin, father of the theory of evolution by natural selection. Darwin published in 1862 the first observations of the fundamental role of insects in orchid pollination, in his book The Fertilization of Orchids. Darwin stated that the varied stratagems orchids use to attract their pollinators transcend the imagination of any human being.