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Names | |
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Preferred IUPAC name 4-(4-Hydroxyphenyl)butan-2-one | |
Other names p-Hydroxybenzyl acetone; 4-(p-Hydroxyphenyl)-2-butanone; Frambinone; Oxyphenylon; Rheosmin; Rasketone | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | RK |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.024.370 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C10H12O2 | |
Molar mass | 164.204 g·mol−1 |
Appearance | White needles [2] |
Melting point | 82 to 84 °C (180 to 183 °F; 355 to 357 K) |
Boiling point | 140 to 146 °C (284 to 295 °F; 413 to 419 K) at 0.5 mmHg |
Hazards | |
GHS labelling: | |
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Warning | |
H302 | |
P264, P270, P301+P312, P330, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries.
Raspberry ketone occurs in a variety of fruits, including raspberries, cranberries, and blackberries. [3] It is detected and released by orchid flowers, e.g. Dendrobium superbum (syn D. anosmum), [4] and several Bulbophyllum species [5] [6] [7] to attract raspberry ketone-responsive male Dacini fruit flies. It is biosynthesized from coumaroyl-CoA. [8] It can be extracted from the fruit, yielding about 1–4 mg per kg of raspberries. [9]
Since the natural abundance of raspberry ketone is very low, it is prepared industrially by a variety of methods from chemical intermediates. [10] One of the ways this can be done is through a Claisen-Schmidt condensation followed by catalytic hydrogenation. First, acetone is condensed with 4-hydroxybenzaldehyde to form an α,β-unsaturated ketone. Then the alkene part is reduced to the alkane. This two-step method produces raspberry ketone in 99% yield. [11] There is a less expensive hydrogenation catalyst, nickel boride, which also demonstrates high selectivity towards hydrogenation of the double bond of enone. [12]
Raspberry ketone is sometimes used in perfumery, in cosmetics, and as a food additive to impart a fruity odor. It is one of the most expensive natural flavor components used in the food industry. The natural compound can cost as much as $20,000 per kg. [9] Synthetic raspberry ketone is cheaper, with estimates ranging from a couple of dollars per pound [13] to one-fifth of the cost of the natural product.[ citation needed ]
Although products containing this compound are marketed for weight loss, there is no clinical evidence for this effect in humans. [14] [15] They are called "ketones", because of the ketone (acetone) group at their end, which is shared with ketone bodies.
Little is known about the long-term safety of raspberry ketone supplements, [16] [17] especially since little research has been done with humans. [18] Toxicological models indicate a potential for cardiotoxic effects, as well as effects on reproduction and development. [16] Furthermore, in many dietary supplements containing raspberry ketones, manufacturers add other ingredients such as caffeine which may have unsafe effects. [18]
In 1965, the US Food and Drug Administration classified raspberry ketone as generally recognized as safe (GRAS) for the small quantities used to flavor foods. [2]
In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.
Orchids are plants that belong to the family Orchidaceae, a diverse and widespread group of flowering plants with blooms that are often colourful and fragrant. Orchids are cosmopolitan plants that are found in almost every habitat on Earth except glaciers. The world's richest diversity of orchid genera and species is found in the tropics.
Mutualism describes the ecological interaction between two or more species where each species has a net benefit. Mutualism is a common type of ecological interaction, one that can come from a parasitic interaction. Prominent examples include most vascular plants engaged in mutualistic interactions with mycorrhizae, flowering plants being pollinated by animals, vascular plants being dispersed by animals, and corals with zooxanthellae, among many others. Mutualism can be contrasted with interspecific competition, in which each species experiences reduced fitness, and exploitation, or parasitism, in which one species benefits at the expense of the other.
In organic chemistry, an acetal is a functional group with the connectivity R2C(OR')2. Here, the R groups can be organic fragments or hydrogen, while the R' groups must be organic fragments not hydrogen. The two R' groups can be equivalent to each other or not. Acetals are formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical stability and reactivity as compared to the analogous carbonyl compounds. The central carbon atom has four bonds to it, and is therefore saturated and has tetrahedral geometry.
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.
Hydrazones are a class of organic compounds with the structure R1R2C=N−NH2. They are related to ketones and aldehydes by the replacement of the oxygen =O with the =N−NH2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.
Zoophily, or zoogamy, is a form of pollination whereby pollen is transferred by animals, usually by invertebrates but in some cases vertebrates, particularly birds and bats, but also by other animals. Zoophilous species frequently have evolved mechanisms to make themselves more appealing to the particular type of pollinator, e.g. brightly colored or scented flowers, nectar, and appealing shapes and patterns. These plant-animal relationships are often mutually beneficial because of the food source provided in exchange for pollination.
Carrion flowers, also known as corpse flowers or stinking flowers, are mimetic flowers that emit an odor that smells like rotting flesh. Apart from the scent, carrion flowers often display additional characteristics that contribute to the mimesis of a decaying corpse. These include their specific coloration, the presence of setae and orifice-like flower architecture. Carrion flowers attract mostly scavenging flies and beetles as pollinators. Some species may trap the insects temporarily to ensure the gathering and transfer of pollen.
Zingerone, also called vanillylacetone, is a major flavor component of ginger, providing the sweet flavor of cooked ginger. Zingerone is a crystalline solid that is sparingly soluble in water and soluble in ether.
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.
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.
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.
Dendrobium christyanum is a species of orchid (Orchidaceae) endemic to the Chinese island of Hainan.
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.
Bulbophyllum nocturnum is a species of epiphytic orchid that grows in New Britain. It was described in 2011, and is the first species of orchid known to consistently flower during the night, and close its flowers during the day.
An attractant is any chemical that attracts an organism, e.g. i) synthetic lures; ii) aggregation and sex pheromones ; and iii) synomone
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.