Shogaol

Last updated
[6]-Shogaol
6-shogaol.svg
Names
Preferred IUPAC name
(4E)-1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one
Other names
  • [6]-Shogaol
  • (E)-[6]-Shogaol
  • Enexasogaol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+ X mark.svgN
    Key: OQWKEEOHDMUXEO-BQYQJAHWSA-N X mark.svgN
  • InChI=1/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
    Key: OQWKEEOHDMUXEO-BQYQJAHWBO
  • CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
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).
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Shogaol
HeatVery 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.

Contents

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.

CompoundScoville Heat Units
(SHU)
Capsaicin16,000,000 [3]
[6]-Shogaol160,000
Piperine100,000
[6]-Gingerol60,000

Shogaols group

[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]

8-shogaol.svg
[8]-shogaol
10-shogaol.svg
[10]-shogaol

Synthesis

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]

Possible synthesis of [6]-shogaol starting from vanillin Wikipedia-shogaol.svg
Possible synthesis of [6]-shogaol starting from vanillin

Related Research Articles

<span class="mw-page-title-main">Scoville scale</span> Scale for measuring spiciness of peppers

The Scoville scale is a measurement of the pungency of chili peppers, as recorded in Scoville Heat Units (SHU), based on the concentration of capsaicinoids, among which capsaicin is the predominant component.

<span class="mw-page-title-main">Ginger</span> Species of plant used as a spice

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.

<span class="mw-page-title-main">Capsaicin</span> Pungent chemical compound in chili peppers

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 chemical irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related alkaloids are called capsaicinoids and are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent, crystalline to waxy solid compound.

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<span class="mw-page-title-main">Maillard reaction</span> Chemical reaction in cooking

The Maillard reaction is a chemical reaction between amino acids and reducing sugars that gives browned food its distinctive flavor. Seared steaks, fried dumplings, cookies and other kinds of biscuits, breads, toasted marshmallows, 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.

<span class="mw-page-title-main">Dipeptide</span>

A dipeptide is an organic compound derived from two amino acids. The constituent amino acids can be the same or different. When different, two isomers of the dipeptide are possible, depending on the sequence. Several dipeptides are physiologically important, and some are both physiologically and commercially significant. A well known dipeptide is aspartame, an artificial sweetener.

Nordihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum).

<span class="mw-page-title-main">Homocapsaicin</span> Chemical compound

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.

<span class="mw-page-title-main">Gingerol</span> Chemical compound

Gingerol, properly as [6]-gingerol, is a phenol phytochemical compound found in fresh ginger that activates spice 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.

<span class="mw-page-title-main">Eucalyptol</span> Chemical compound

Eucalyptol is a monoterpenoid. A colorless liquid, it is a bicyclic ether. Eucalyptol has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up 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.

<span class="mw-page-title-main">Zingerone</span> Chemical compound

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.

<span class="mw-page-title-main">Zingiberene</span> Chemical compound

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.

<i>Kaempferia galanga</i> Species of flowering plant

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.

<span class="mw-page-title-main">Paradol</span> Chemical compound

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.

<i>Zingiber cassumunar</i> Species of flowering plant

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.

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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.

References

  1. 1 2 Compton, Richard G.; Batchelor-McAuley, Christopher; Ngamchuea, Kamonwad; Chaisiwamongkhol, Korbua (2016-10-31). "Electrochemical detection and quantification of gingerol species in ginger (Zingiber officinale) using multiwalled carbon nanotube modified electrodes". Analyst. 141 (22): 6321–6328. Bibcode:2016Ana...141.6321C. doi:10.1039/C6AN02254E. ISSN   1364-5528. PMID   27774555. S2CID   40241982.
  2. Harold McGee (2004). On Food and Cooking: The Science and Lore of the Kitchen (2nd ed.). New York: Scribner. pp. 425–426.
  3. Govindarajan, Sathyanarayana (1991). "Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences". Critical Reviews in Food Science and Nutrition. 29 (6): 435–474. doi:10.1080/10408399109527536. PMID   2039598.
  4. "Analysis of Chemical Properties of Edible and Medicinal Ginger by Metabolomics Approach : Table 1" . Retrieved 3 December 2016.
  5. NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography[ full citation needed ]
  6. Hung-Cheng Shih; et al. (March 2014). "Synthesis of Analogues of Gingerol and Shogaol, the Active Pungent Principles from the Rhizomes of Zingiber officinale and Evaluation of Their Anti-Platelet Aggregation Effects". International Journal of Molecular Sciences . 15 (3): 3926–3951. doi: 10.3390/ijms15033926 . PMC   3975376 . PMID   24599082.