Homodihydrocapsaicin

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Homodihydrocapsaicin
Homodihydrocapsaicin.svg
Names
Preferred IUPAC name
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-9-methyldecanamide
Other names
  • Homodihydrocapsaicin
  • N-Vanillyl-9-methyldecanamide
  • Vanillylamide of 9-methyldecanoic acid
  • HDHC
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C19H31NO3/c1-15(2)9-7-5-4-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h11-13,15,21H,4-10,14H2,1-3H3,(H,20,22) X mark.svgN
    Key: AKDLSISGGARWFP-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C19H31NO3/c1-15(2)9-7-5-4-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h11-13,15,21H,4-10,14H2,1-3H3,(H,20,22)
    Key: AKDLSISGGARWFP-UHFFFAOYAS
  • O=C(NCc1cc(OC)c(O)cc1)CCCCCCCC(C)C
Properties
C19H31NO3
Molar mass 321.461 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Homodihydrocapsaicin
HeatAbove peak
Scoville scale 8,600,000 [1] SHU

Homodihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers ( Capsicum ). Like capsaicin it is an irritant. Homodihydrocapsaicin accounts for about 1% of the total capsaicinoids mixture [2] and has about half the pungency of capsaicin. Pure homodihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It produces "numbing burn" in the throat and is one of the most prolonged and difficult to rinse out. On the Scoville scale it has 8,600,000 SHU (Scoville heat units). [1]

Contents

See also

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 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.

<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 and neurotoxin 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, probably as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent, crystalline to waxy solid compound.

<span class="mw-page-title-main">Bell pepper</span> Group of fruits of Capsicum annuum

The bell pepper is the fruit of plants in the Grossum Group of the species Capsicum annuum. Cultivars of the plant produce fruits in different colors, including red, yellow, orange, green, white, chocolate, candy cane striped, and purple. Bell peppers are sometimes grouped with less pungent chili varieties as "sweet peppers". While they are botanically fruits—classified as berries—they are commonly used as a vegetable ingredient or side dish. Other varieties of the genus Capsicum are categorized as chili peppers when they are cultivated for their pungency, including some varieties of Capsicum annuum.

<span class="mw-page-title-main">Chili pepper</span> Varieties of peppers belonging to several species of Capsicum genus

Chili peppers, from Nahuatl chīlli, are varieties of the berry-fruit of plants from the genus Capsicum, which are members of the nightshade family Solanaceae, cultivated for their pungency. Chili peppers are widely used in many cuisines as a spice to add "heat" to dishes. Capsaicin and related compounds known as capsaicinoids are the substances giving chili peppers their intensity when ingested or applied topically. Chili peppers exhibit a wide range of heat and flavor profiles. This diversity is the reason behind the availability of different types of paprika and chili powder, each offering its distinctive taste and heat level.

<span class="mw-page-title-main">Jalapeño</span> Hot pepper

The jalapeño is a medium-sized chili pepper pod type cultivar of the species Capsicum annuum. A mature jalapeño chili is 5–10 cm (2–4 in) long and hangs down with a round, firm, smooth flesh of 25–38 mm wide. It can have a range of pungency, with Scoville heat units of 4,000 to 8,500. Commonly picked and consumed while still green, it is occasionally allowed to fully ripen and turn red, orange, or yellow. It is wider and generally milder than the similar Serrano pepper.

<i>Capsicum pubescens</i> Species of plant

Capsicum pubescens is a plant of the genus Capsicum (pepper). The species name, pubescens, refers to the hairy leaves of this pepper. The hairiness of the leaves, along with the black seeds, make Capsicum pubescens distinguishable from other Capsicum species. Capsicum pubescens has pungent yellow, orange, red, green or brown fruits.

<span class="mw-page-title-main">Hot sauce</span> Chili pepper-based condiment

Hot sauce is a type of condiment, seasoning, or salsa made from chili peppers and other ingredients. Many commercial varieties of mass-produced hot sauce exist.

<i>Capsicum annuum <span style="font-style:normal;">var.</span> glabriusculum</i> Variety of chili pepper

Capsicum annuum var. glabriusculum, a chili-pepper variety of Capsicum annuum, is native to southern North America and northern South America. Common names include chiltepín, Indian pepper, chiltepe, and chile tepín, as well as turkey, bird’s eye, or simply bird peppers. Tepín is derived from a Nahuatl word meaning "flea". This variety is the most likely progenitor of the domesticated C. annuum var. annuum. Another similar-sized pepper, 'Pequin' is often confused with tepin, although the tepin fruit is round to oval where as the pequin's fruit is oval with a point, and the leaves, stems and plant structures are very different on each plant.

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

Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin, it is an irritant. It accounts for about 22% of the total capsaicinoid mixture and has the same pungency as capsaicin. Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is soluble in dimethyl sulfoxide and 100% ethanol.

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.

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">Shogaol</span> Chemical compound

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.

Capsinoids are alkaloid substances naturally present in chili peppers. Although they are structurally similar to capsaicin, the substance that causes pungency in hot peppers, they largely lack that characteristic. Capsinoids have an estimated "hot taste threshold" which is about 1/1000 that of capsaicin. Capsinoids were not reported in the scientific literature until 1989, when biologists first isolated them in a unique variety of chili peppers, CH-19 Sweet, which does not contain capsaicin. Capsinoids include capsiate, dihydrocapsiate, and nordihydrocapsiate.

<span class="mw-page-title-main">Carolina Reaper</span> Exceptionally hot cultivar of the Capsicum pepper

The Carolina Reaper chili pepper is a cultivar of the Capsicum chinense plant. Developed by American breeder Ed Currie, the pepper is red and gnarled, with a bumpy texture and small pointed tail. In 2013, Guinness World Records declared it as the hottest chili pepper in the world.

<span class="mw-page-title-main">Ghost pepper</span> Chili pepper cultivated in Northeast India

The ghost pepper, also known as bhut jolokia, is an interspecific hybrid chili pepper cultivated in Northeast India. It is a hybrid of Capsicum chinense and Capsicum frutescens.

<span class="mw-page-title-main">Hot pepper challenge</span>

The hot pepper challenge is an Internet viral video fad, consisting of a food challenge that involves filming oneself while eating and swallowing a chili pepper that is high on the Scoville scale and known for its piquant (spicy-hot) qualities, in particular the cayenne pepper, Thai pepper, habanero, ghost pepper, and the Trinidad moruga scorpion pepper; the video is then uploaded to the Internet. Hot pepper challenges have been featured on television series, including Man v. Food.

<i>Capsicum</i> Genus of flowering plants

Capsicum is a genus of flowering plants in the nightshade family Solanaceae, native to the Americas, cultivated worldwide for their chili pepper or bell pepper fruit.

<span class="mw-page-title-main">Habanero</span> Strain of chili (Capsicum)

The habanero is a hot variety of chili. Unripe habaneros are green, and they color as they mature. The most common color variants are orange and red, but the fruit may also be white, brown, yellow, green, or purple. Typically, a ripe habanero is 2–6 centimetres long. Habanero chilis are very hot, rated 100,000–350,000 on the Scoville scale. The habanero's heat, flavor, and floral aroma make it a popular ingredient in hot sauces and other spicy foods.

Pepper X is a cultivar of Capsicum chili pepper bred by Ed Currie, creator of the Carolina Reaper. Pepper X resulted from several cross breedings that produced an exceptionally high content of capsaicin in the locules of the pepper. The exceptional pungency of the chili was developed over 10 years of cultivation.

References

  1. 1 2 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.
  2. Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin". J. Chem. Soc. C: 442. doi:10.1039/j39680000442.