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Preferred IUPAC name (4E)-1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one | |
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Properties | |
C17H24O3 | |
Molar mass | 276.376 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Shogaol | |
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Heat | Very hot (chemical) |
Scoville scale | 160,000 [1] SHU |
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. [2] Moreover, shogaol (and gingerol) are converted to other constituents when heat is applied over time, which is why ginger loses its spiciness as it is cooked.
The name shogaol is derived from the Japanese name for ginger (生姜、shōga).
Shogaol is rated 160,000 SHU on the Scoville scale. [1] When compared to other pungent compounds, shogaol is moderately more pungent than piperine, but less than capsaicin.
Compound | Scoville Heat Units (SHU) |
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Capsaicin | 16,000,000 [3] |
[6]-Shogaol | 160,000 |
Piperine | 100,000 |
[6]-Gingerol | 60,000 |
[4]-Shogaol, [8]-shogaol, [10]-shogaol, and [12]-shogaol (all found in ginger) together constitute the group shogaols. There also exist in ginger cultivars methylated shogaols: methyl [6]-shogaol and methyl [8]-shogaol, respectively. [4]
Shogaols are artifacts formed during storage or through excess heat, probably created by a dehydration reaction of the gingerols. The ratio of shogaols to gingerols sometimes is taken as an indication of product quality. [5]
A possible synthesis starts with a Claisen condensation of vanillin and acetone, producing dehydrozingerone. Afterwards the product reacts in an aldol condensation with hexanal in tetrahydrofurane to 6-dehydroshogaol and 6-dehydrogingerol. Latter can be hydrogenated to [6]-gingerol by a catalyst. In the last step hydrochloric acid is added to get the desired [6]-shogaol. [6]
Turmeric, ,) 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.
The Scoville scale is a measurement of pungency of chili peppers and other substances, recorded in Scoville heat units (SHU). It is based on the concentration of capsaicinoids, among which capsaicin is the predominant component.
Ginger is a flowering plant whose rhizome, ginger root or ginger, is widely used as a spice and a folk medicine. It is an herbaceous perennial that 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.
Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a potent irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, likely as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent crystalline solid.
An antiemetic is a drug that is effective against vomiting and nausea. Antiemetics are typically used to treat motion sickness and the side effects of opioid analgesics, general anaesthetics, and chemotherapy directed against cancer. They may be used for severe cases of gastroenteritis, especially if the patient is dehydrated.
The Maillard reaction is a chemical reaction between amino acids and reducing sugars to create melanoidins, the compounds that give browned food its distinctive flavor. Seared steaks, fried dumplings, cookies and other kinds of biscuits, breads, toasted marshmallows, falafel and many other foods undergo this reaction. It is named after French chemist Louis Camille Maillard, who first described it in 1912 while attempting to reproduce biological protein synthesis. The reaction is a form of non-enzymatic browning which typically proceeds rapidly from around 140 to 165 °C. Many recipes call for an oven temperature high enough to ensure that a Maillard reaction occurs. At higher temperatures, caramelization and subsequently pyrolysis become more pronounced.
Homocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Homocapsaicin accounts for about 1% of the total capsaicinoids mixture and has about half the pungency of capsaicin. Pure homocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. On the Scoville scale it has 8,600,000 SHU. Homocapsaicin isolated from chili pepper has been found in two isomeric forms, both with a carbon-carbon double bond at the 6 position on the 10-carbon acyl chain. One isomer has an additional carbon, a methyl group, at the 8 position and the other has a methyl group at the 9 position. Homocapsaicin (6-ene-8-methyl) is the more abundant isomer. Homocapsaicin with the double bond at the 7 position has never been found in nature, though its structure is widely reported on the Internet and in the scientific literature. Details of this misidentification have been published.
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.
Eucalyptol is a monoterpenoid colorless liquid, and a bicyclic ether. It has a fresh camphor-like odor and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.
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.
Zingiberene is a monocyclic sesquiterpene that is the predominant constituent of the oil of ginger, from which it gets its name. It can contribute up to 30% of the essential oils in ginger rhizomes. This is the compound that gives ginger its distinct flavoring.
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.
Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.
Paradol is the active flavor constituent of the seeds of Guinea pepper. It is also found in ginger. Paradol has been found to have antioxidant and antitumor promoting effects in a mouse model.
Gluconasturtiin or phenethyl glucosinolate is one of the most widely distributed glucosinolates in the cruciferous vegetables, mainly in the roots, and is probably one of the plant compounds responsible for the natural pest-inhibiting properties of growing crucifers, such as cabbage, mustard or rape, in rotation with other crops. This effect of gluconasturtiin is due to its degradation by the plant enzyme myrosinase into phenethyl isothiocyanate, which is toxic to many organisms.
Cassumunar ginger: Zingiber cassumunar, now thought to be a synonym of Zingiber montanum (J.König) Link ex A.Dietr., is a species of plant in the ginger family and is also a relative of galangal. It is called plai (ไพล) in Thailand, in addition to in Isan language and in northern Thai language. The rhizome of variant 'Roxburgh' is used medicinally in massage and even in food in Thailand, and somewhat resembles ginger root or galangal. In aromatherapy, plai oil is used as an essential oil and is believed to ease pain and inflammation. It is also known as ponlei (ពន្លៃ) in Cambodia.
Zingibain, zingipain, or ginger protease is a cysteine protease enzyme found in ginger rhizomes. It catalyses the preferential cleavage of peptides with a proline residue at the P2 position. It has two distinct forms, ginger protease I (GP-I) and ginger protease II (GP-II).
1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one is a natural product, a curcuminoid antioxidant found in turmeric and torch ginger.
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.
Colin Llewellyn Raston is a Professor of Chemistry of Flinders University in Adelaide, South Australia and the Premier's Professorial Fellow in Clean Technology. In 2015, he was awarded an Ig Nobel Prize in "for inventing a chemical recipe to partially un-boil an egg". In 2016, Raston was made an Officer of the Order of Australia for his services to science.