Names | |
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Preferred IUPAC name (1E,4E,6E)-1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one | |
Identifiers | |
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3D model (JSmol) |
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ChEBI |
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ChEMBL |
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ChemSpider | |
PubChem CID |
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Properties [2] | |
C19H16O3 | |
Molar mass | 292.334 g·mol−1 |
Appearance | Yellow powder |
Melting point | 168–170 °C (334–338 °F; 441–443 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one is a natural product, a curcuminoid antioxidant found in turmeric (Curcuma longa) and torch ginger (Etlingera elatior). [3] [4]
The all-trans double bond isomer (1E,4E,6E)-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one was first fully characterised when isolated from extracts of the rhizomes of turmeric (Curcuma longa) in 1993. [5] It has subsequently been found in other species, including etlingera elatior . [2] A very large number of similar compounds are found in turmeric [6] and ginger. [7] These have been extensively studied in their roles as antioxidants and for their potential pharmacological properties.
The (1Z) double bond isomer is poorly characterised in the literature and it and the compounds with unspecified stereochemistry may in fact be the parent all-E molecule.
Mohamad et al. (2005) found that the curcuminoids 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one, demethoxycurcumin, and 16-hydroxylabda-8(17),11,13-trien-15,16-olide inhibit lipid peroxidation more potently than does alpha-tocopherol. [4]
Turmeric or Curcuma longa, is a flowering plant in the ginger family Zingiberaceae. It is a perennial, rhizomatous, herbaceous plant native to the Indian subcontinent and Southeast Asia that requires temperatures between 20 and 30 °C and high annual rainfall to thrive. Plants are gathered each year for their rhizomes, some for propagation in the following season and some for consumption.
Zingiberaceae or the ginger family is a family of flowering plants made up of about 50 genera with a total of about 1600 known species of aromatic perennial herbs with creeping horizontal or tuberous rhizomes distributed throughout tropical Africa, Asia, and the Americas. Many of the family's species are important ornamental, spice, or medicinal plants. Ornamental genera include the shell gingers (Alpinia), Siam or summer tulip, Globba, ginger lily (Hedychium), Kaempferia, torch-ginger Etlingera elatior, Renealmia, and ginger (Zingiber). Spices include ginger (Zingiber), galangal or Thai ginger, melegueta pepper, myoga, korarima, turmeric (Curcuma), and cardamom.
Ginger is a flowering plant whose rhizome, ginger root or ginger, is widely used as a spice and a folk medicine. It is a herbaceous perennial which grows annual pseudostems about one meter tall, bearing narrow leaf blades. The inflorescences bear flowers having pale yellow petals with purple edges, and arise directly from the rhizome on separate shoots.
Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.
Curcumin is a bright yellow chemical produced by plants of the Curcuma longa species. It is the principal curcuminoid of turmeric, a member of the ginger family, Zingiberaceae. It is sold as a herbal supplement, cosmetics ingredient, food flavoring, and food coloring.
Curcuma zedoaria is a perennial herb and member of the genus Curcuma, family Zingiberaceae. The plant is native to South Asia and Southeast Asia but is now naturalized in other places including the US state of Florida. Zedoary was one of the ancient food plants of the Austronesian peoples. They were spread during prehistoric times to the Pacific Islands and Madagascar during the Austronesian expansion. Its use as a spice in the West today is extremely rare, having been replaced by ginger, and to a lesser extent, yellow turmeric.
Gingerol ([6]-gingerol) is a phenolic phytochemical compound found in fresh ginger that activates heat receptors on the tongue. It is normally found as a pungent yellow oil in the ginger rhizome, but can also form a low-melting crystalline solid. This chemical compound is found in all members of the Zingiberaceae family and is high in concentrations in the grains of paradise as well as an African Ginger species.
The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes. α-Farnesene and β-farnesene are isomers, differing by the location of one double bond. α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. The alpha form can exist as four stereoisomers that differ about the geometry of two of its three internal double bonds. The beta isomer exists as two stereoisomers about the geometry of its central double bond.
Etlingera elatior is a species of herbaceous perennial plant in the family Zingiberaceae; it is native to Indonesia, Thailand, Malaysia and New Guinea.
Pinosylvin is an organic compound with the formula C6H5CH=CHC6H3(OH)2. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.
Kaempferia galanga, commonly known as kencur, aromatic ginger, sand ginger, cutcherry, is a monocotyledonous plant in the ginger family, and one of four plants called galangal. It is found primarily in open areas in Indonesia, southern China, Taiwan, Cambodia, and India, but is also widely cultivated throughout Southeast Asia.
A curcuminoid is a linear diarylheptanoid, a relatively small class of plant secondary metabolites that includes curcumin, demethoxycurcumin, and bisdemethoxycurcumin, all isolated from turmeric. These compounds are natural phenols and produce a pronounced yellow color that is often used to color foods and medicines. Curcumin is obtained from the root of turmeric.
Curcuma caesia, black turmeric or black zedoary, is a perennial herb with bluish-black rhizomes that is native to northeast India.
Etlingera fulgens is a species of herbaceous perennial plant of the family Zingiberaceae. This species occurs in southern Thailand and peninsular Malaysia. E. fulgens is used as an ornamental plant in landscape gardens for its bright red flowers and young leaves.
Desmethoxycurcumin is a curcuminoid found in turmeric. Commercial grade curcumin contains a mixture of curcuminoids.
The diarylheptanoids are polyphenols and a relatively small class of plant secondary metabolites. Diarylheptanoids consist of two aromatic rings joined by a seven carbons chain (heptane) and having various substituents. They can be classified into linear (curcuminoids) and cyclic diarylheptanoids. The best known member is curcumin, which is isolated from turmeric and is known as food coloring E100. Some other Curcuma species, such as Curcuma comosa also produce diarylheptanoids.
Microsporum nanum is a pathogenic fungus in the family Arthrodermataceae. It is a type of dermatophyte that causes infection in dead keratinized tissues such as skin, hair, and nails. Microsporum nanum is found worldwide and is both zoophilic and geophilic. Animals such as pigs and sheep are the natural hosts for the fungus; however, infection of humans is also possible. Majority of the human cases reported are associated with pig farming. The fungus can invade the skin of the host; if it is scratched off by the infected animal, the fungus is still capable of reproducing in soil.
Curcumin synthase categorizes three enzyme isoforms, type III polyketide synthases (PKSs) present in the leaves and rhizome of the turmeric plant that synthesize curcumin. CURS1-3 are responsible for the hydrolysis of feruloyldiketide-CoA, previously produced in the curcuminoid pathway, and a decarboxylative condensation reaction that together comprise one of the final steps in the synthesis pathway for curcumin, demethoxycurcumin, and bisdemethoxycurcumin, the compounds that give turmeric both its distinctive yellow color, and traditional medical benefits. CURS should not be confused with Curcuminoid Synthase (CUS), which catalyzes the one-pot synthesis of bisdemethoxycurcumin in Oryza sativa.
Rosemary Margaret Smith (1933–2004) was a Scottish botanist and illustrator who specialized in the taxonomy of the Zingiberaceae, or ginger family. Many of the species she classified and identified as being placed into improper genera were found in Asian countries, especially in the isolated island of Borneo.
Tumerones are a group of related chemical compounds of the sesquiterpene class. They are found in turmeric, from which they derive their name, as well as other related plants such as Curcuma caesia. There are multiple structural types of turmerones which differ in the number and placement of double bonds including α-tumerone, β-turmerone, and ar-turmerone. Each of these types consists of multiple stereoisomers.