Capsaicin

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Capsaicin
Capsaicin.svg
Capsaicin-3D-vdW.png
Names
Pronunciation /kæpˈseɪsɪn/ or /kæpˈseɪəsɪn/
Preferred IUPAC name
(6E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Other names
(E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
8-Methyl-N-vanillyl-trans-6-nonenamide
trans-8-Methyl-N-vanillylnon-6-enamide
(E)-Capsaicin
Capsicine
Capsicin
CPS
Identifiers
3D model (JSmol)
2816484
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.337 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-969-8
KEGG
PubChem CID
UNII
  • InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+ Yes check.svgY
    Key: YKPUWZUDDOIDPM-SOFGYWHQSA-N Yes check.svgY
  • InChI=1/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
    Key: YKPUWZUDDOIDPM-SOFGYWHQBQ
  • O=C(NCc1cc(OC)c(O)cc1)CCCC/C=C/C(C)C
Properties
C18H27NO3
Molar mass 305.418 g·mol−1
AppearanceCrystalline white powder [1]
Odor Highly pungent
Melting point 62 to 65 °C (144 to 149 °F; 335 to 338 K)
Boiling point 210 to 220 °C (410 to 428 °F; 483 to 493 K) 0.01 Torr
0.0013 g/100 mL
Solubility
Vapor pressure 1.32×10−8 mm Hg at 25 °C [2]
UV-vis (λmax)280 nm
Structure
Monoclinic
Pharmacology
M02AB01 ( WHO ) N01BX04 ( WHO )
License data
Legal status
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H301, H302, H315, H318
P264, P270, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Safety data sheet (SDS) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Capsaicin
HeatAbove peak
(pure capsaicin is toxic) [2]
Scoville scale 16,000,000 [5] SHU

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) ( /kæpˈseɪsɪn/ or /kæpˈseɪəsɪn/ ) 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. [6] Pure capsaicin is a hydrophobic, colorless, highly pungent (i.e., spicy) crystalline solid. [2]

Natural function

Capsaicin is present in large quantities in the placental tissue (which holds the seeds), the internal membranes and, to a lesser extent, the other fleshy parts of the fruits of plants in the genus Capsicum . The seeds themselves do not produce any capsaicin, although the highest concentration of capsaicin can be found in the white pith of the inner wall, where the seeds are attached. [7]

The seeds of Capsicum plants are dispersed predominantly by birds. In birds, the TRPV1 channel does not respond to capsaicin or related chemicals but mammalian TRPV1 is very sensitive to it. This is advantageous to the plant, as chili pepper seeds consumed by birds pass through the digestive tract and can germinate later, whereas mammals have molar teeth which destroy such seeds and prevent them from germinating. Thus, natural selection may have led to increasing capsaicin production because it makes the plant less likely to be eaten by animals that do not help it disperse. [8] There is also evidence that capsaicin may have evolved as an anti-fungal agent. [9] The fungal pathogen Fusarium , which is known to infect wild chilies and thereby reduce seed viability, is deterred by capsaicin, which thus limits this form of predispersal seed mortality.

The vanillotoxin-containing venom of a certain tarantula species ( Psalmopoeus cambridgei) activates the same pathway of pain as is activated by capsaicin, an example of a shared pathway in both plant and animal anti-mammalian defense. [10]

Uses

Food

Curry dishes Karnatakadishes.jpg
Curry dishes

Because of the burning sensation caused by capsaicin when it comes in contact with mucous membranes, it is commonly used in food products to provide added spiciness or "heat" (piquancy), usually in the form of spices such as chili powder and paprika. [11] In high concentrations, capsaicin will also cause a burning effect on other sensitive areas, such as skin or eyes. [12] The degree of heat found within a food is often measured on the Scoville scale. [11]

There has long been a demand for capsaicin-spiced products like chili pepper, and hot sauces such as Tabasco sauce and Mexican salsa. [11] It is common for people to experience pleasurable and even euphoric effects from ingesting capsaicin. [11] Folklore among self-described "chiliheads" attribute this to pain-stimulated release of endorphins, a different mechanism from the local receptor overload that makes capsaicin effective as a topical analgesic. [12]

Research and pharmaceutical use

Capsaicin is used as an analgesic in topical ointments and dermal patches to relieve pain, typically in concentrations between 0.025% and 0.1%. [13] It may be applied in cream form for the temporary relief of minor aches and pains of muscles and joints associated with arthritis, backache, strains and sprains, often in compounds with other rubefacients. [13]

It is also used to reduce the symptoms of peripheral neuropathy, such as post-herpetic neuralgia caused by shingles. [13] A capsaicin transdermal patch (Qutenza) for the management of this particular therapeutic indication (pain due to post-herpetic neuralgia) was approved in 2009, as a therapeutic by both the U.S. Food and Drug Administration (FDA) [14] [15] and the European Union. [16] A subsequent application to the FDA for Qutenza to be used as an analgesic in HIV neuralgia was refused. [17] One 2017 review of clinical studies having limited quality found that high-dose topical capsaicin (8%) compared with control (0.4% capsaicin) provided moderate to substantial pain relief from post-herpetic neuralgia, HIV-neuropathy, and diabetic neuropathy. [18]

Although capsaicin creams have been used to treat psoriasis for reduction of itching, [13] [19] [20] a review of six clinical trials involving topical capsaicin for treatment of pruritus concluded there was insufficient evidence of effect. [21] Oral capsaicin decreases LDL cholesterol levels moderately. [22]

There is insufficient clinical evidence to determine the role of ingested capsaicin on several human disorders, including obesity, diabetes, cancer and cardiovascular diseases. [13]

Pepper spray and pests

Capsaicinoids are also an active ingredient in riot control and personal defense pepper spray agents. [2] When the spray comes in contact with skin, especially eyes or mucous membranes, it produces pain and breathing difficulty in the affected individual. [2]

Capsaicin is also used to deter pests, specifically mammalian pests. Targets of capsaicin repellants include voles, deer, rabbits, squirrels, bears, insects, and attacking dogs. [23] Ground or crushed dried chili pods may be used in birdseed to deter rodents, [24] taking advantage of the insensitivity of birds to capsaicin. The Elephant Pepper Development Trust claims that using chili peppers as a barrier crop can be a sustainable means for rural African farmers to deter elephants from eating their crops. [25]

An article published in the Journal of Environmental Science and Health Part B in 2006 states that "Although hot chili pepper extract is commonly used as a component of household and garden insect-repellent formulas, it is not clear that the capsaicinoid elements of the extract are responsible for its repellency." [26]

The first pesticide product using solely capsaicin as the active ingredient was registered with the U.S. Department of Agriculture in 1962. [23]

Equestrian sports

Capsaicin is a banned substance in equestrian sports because of its hypersensitizing and pain-relieving properties. [27] At the show jumping events of the 2008 Summer Olympics, four horses tested positive for capsaicin, which resulted in disqualification. [27]

Irritant effects

Acute health effects

Capsaicin is a strong irritant requiring proper protective goggles, respirators, and proper hazardous material-handling procedures. Capsaicin takes effect upon skin contact (irritant, sensitizer), eye contact (irritant), ingestion, and inhalation (lung irritant, lung sensitizer). The LD50 in mice is 47.2 mg/kg. [28] [29]

Painful exposures to capsaicin-containing peppers are among the most common plant-related exposures presented to poison centers. [30] They cause burning or stinging pain to the skin and, if ingested in large amounts by adults or small amounts by children, can produce nausea, vomiting, abdominal pain, and burning diarrhea. Eye exposure produces intense tearing, pain, conjunctivitis, and blepharospasm. [31]

Treatment after exposure

The primary treatment is removal of the offending substance. Plain water is ineffective at removing capsaicin. [28] Capsaicin is soluble in alcohol, which can be used to clean contaminated items. [28]

When capsaicin is ingested, cold milk may be an effective way to relieve the burning sensation due to caseins in milk, and the water of milk acts as a surfactant, allowing the capsaicin to form an emulsion with it. [32]

Weight loss and regain

As of 2007, there was no evidence showing that weight loss is directly correlated with ingesting capsaicin. Well-designed clinical research had not been performed because the pungency of capsaicin in prescribed doses under research prevented subjects from complying in the study. [33] A 2014 meta-analysis of further trials found weak evidence that consuming capsaicin before a meal might slightly reduce the amount of food consumed, and might drive food preference toward carbohydrates. [34]

Peptic ulcer

One 2006 review concluded that capsaicin may relieve symptoms of a peptic ulcer rather than being a cause of it. [35]

Death

Ingestion of high quantities of capsaicin can be deadly, [36] particularly in people with heart problems. [37] Even healthy young people can suffer adverse health effects like myocardial infarction after ingestion of capsaicin capsules. [38]

Mechanism of action

The burning and painful sensations associated with capsaicin result from "defunctionalization" of nociceptor nerve fibers by causing a topical hypersensitivity reaction in the skin. [2] [39] As a member of the vanilloid family, capsaicin binds to a receptor on nociceptor fibers called the vanilloid receptor subtype 1 (TRPV1). [39] [40] [41] TRPV1, which can also be stimulated with heat, protons and physical abrasion, permits cations to pass through the cell membrane when activated. [39] The resulting depolarization of the neuron stimulates it to send impulses to the brain. [39] By binding to TRPV1 receptors, capsaicin produces similar sensations to those of excessive heat or abrasive damage, such as warming, tingling, itching, or stinging, explaining why capsaicin is described as an irritant on the skin and eyes or by ingestion. [39]

Clarifying the mechanisms of capsaicin effects on skin nociceptors was part of awarding the 2021 Nobel Prize in Physiology or Medicine, as it led to the discovery of skin sensors for temperature and touch, and identification of the single gene causing sensitivity to capsaicin. [42] [43]

History

The compound was first extracted in impure form in 1816 by Christian Friedrich Bucholz (1770–1818). [44] [lower-alpha 1] In 1873 German pharmacologist Rudolf Buchheim [54] [55] [56] (1820–1879) and in 1878 the Hungarian doctor Endre Hőgyes [57] [58] stated that "capsicol" (partially purified capsaicin [59] ) caused the burning feeling when in contact with mucous membranes and increased secretion of gastric acid.

Capsaicinoids

The most commonly occurring capsaicinoids are capsaicin (69%), dihydrocapsaicin (22%), nordihydrocapsaicin (7%), homocapsaicin (1%), and homodihydrocapsaicin (1%). [60]

Capsaicin and dihydrocapsaicin (both 16.0 million SHU) are the most pungent capsaicinoids. Nordihydrocapsaicin (9.1 million SHU), homocapsaicin and homodihydrocapsaicin (both 8.6 million SHU) are about half as hot. [5]

There are six natural capsaicinoids (table below). Although vanillylamide of n-nonanoic acid (Nonivamide, VNA, also PAVA) is produced synthetically for most applications, it does occur naturally in Capsicum species. [61]

Capsaicinoid nameAbbrev.Typical
relative
amount		 Scoville
heat units		Chemical structure
CapsaicinCPS 69%16,000,000 Kapsaicyna.svg
Dihydrocapsaicin DHC22%16,000,000 Dihydrocapsaicin.svg
Nordihydrocapsaicin NDHC7%9,100,000 Nordihydrocapsaicin chemical structure.png
Homocapsaicin HC1%8,600,000 Homocapsaicin.svg
Homodihydrocapsaicin HDHC1%8,600,000 Homodihydrocapsaicin.svg
Nonivamide PAVA9,200,000 Nonivamide.svg

Biosynthesis

Chili peppers BhutJolokia09 Asit.jpg
Chili peppers
Vanillamine is a product of the phenylpropanoid pathway. Vanillamine biosynthesis.gif
Vanillamine is a product of the phenylpropanoid pathway.
Valine enters the branched fatty acid pathway to produce 8-methyl-6-nonenoyl-CoA. 8-methyl-6-nonenoyl biosynthesis.gif
Valine enters the branched fatty acid pathway to produce 8-methyl-6-nonenoyl-CoA.
Capsaicin synthase condenses vanillamine and 8-methyl-6-nonenoyl-CoA to produce capsaicin. Condensation to capsaicin.gif
Capsaicin synthase condenses vanillamine and 8-methyl-6-nonenoyl-CoA to produce capsaicin.

History

The general biosynthetic pathway of capsaicin and other capsaicinoids was elucidated in the 1960s by Bennett and Kirby, and Leete and Louden. Radiolabeling studies identified phenylalanine and valine as the precursors to capsaicin. [62] [63] Enzymes of the phenylpropanoid pathway, phenylalanine ammonia lyase (PAL), cinnamate 4-hydroxylase (C4H), caffeic acid O-methyltransferase (COMT) and their function in capsaicinoid biosynthesis were identified later by Fujiwake et al., [64] [65] and Sukrasno and Yeoman. [66] Suzuki et al. are responsible for identifying leucine as another precursor to the branched-chain fatty acid pathway. [67] It was discovered in 1999 that pungency of chili peppers is related to higher transcription levels of key enzymes of the phenylpropanoid pathway, phenylalanine ammonia lyase, cinnamate 4-hydroxylase, caffeic acid O-methyltransferase. Similar studies showed high transcription levels in the placenta of chili peppers with high pungency of genes responsible for branched-chain fatty acid pathway. [68]

Biosynthetic pathway

Plants exclusively of the genus Capsicum produce capsaicinoids, which are alkaloids. [69] Capsaicin is believed to be synthesized in the interlocular septum of chili peppers and depends on the gene AT3, which resides at the pun1 locus, and which encodes a putative acyltransferase. [70]

Biosynthesis of the capsaicinoids occurs in the glands of the pepper fruit where capsaicin synthase condenses vanillylamine from the phenylpropanoid pathway with an acyl-CoA moiety produced by the branched-chain fatty acid pathway. [63] [71] [72] [73]

Capsaicin is the most abundant capsaicinoid found in the genus Capsicum , but at least ten other capsaicinoid variants exist. [74] Phenylalanine supplies the precursor to the phenylpropanoid pathway while leucine or valine provide the precursor for the branched-chain fatty acid pathway. [63] [71] To produce capsaicin, 8-methyl-6-nonenoyl-CoA is produced by the branched-chain fatty acid pathway and condensed with vanillylamine. Other capsaicinoids are produced by the condensation of vanillylamine with various acyl-CoA products from the branched-chain fatty acid pathway, which is capable of producing a variety of acyl-CoA moieties of different chain length and degrees of unsaturation. [75] All condensation reactions between the products of the phenylpropanoid and branched-chain fatty acid pathway are mediated by capsaicin synthase to produce the final capsaicinoid product. [63] [71]

Evolution

The Capsicum genus split from Solanaceae 19.6 million years ago, 5.4 million years after the appearance of Solanaceae, and is native only to the Americas. [76] Chilies only started to quickly evolve in the past 2 million years into markedly different species. This evolution can be partially attributed to a key compound found in peppers, 8-methyl-N-vanillyl-6-nonenamide, otherwise known as capsaicin. Capsaicin evolved similarly across species of chilies that produce capsaicin. Its evolution over the course of centuries is due to genetic drift and natural selection, across the genus Capsicum . Despite the fact that chilies within the Capsicum genus are found in diverse environments, the capsaicin found within them all exhibit similar properties that serve as defensive and adaptive features. Capsaicin evolved to preserve the fitness of peppers against fungi infections, insects, and granivorous mammals. [77]

Antifungal properties

Capsaicin acts as an antifungal agent in four primary ways. First, capsaicin inhibits the metabolic rate of the cells that make up the fungal biofilm. [78] This inhibits the area and growth rate of the fungus, since the biofilm creates an area where a fungus can grow and adhere to the chili in which capsaicin is present. [79] Capsaicin also inhibits fungal hyphae formation, which impacts the amount of nutrients that the rest of the fungal body can receive. [80] Thirdly, capsaicin disrupts the structure [81] of fungal cells and the fungal cell membranes. This has consequential negative impacts on the integrity of fungal cells and their ability to survive and proliferate. Additionally, the ergosterol synthesis of growing fungi decreases in relation to the amount of capsaicin present in the growth area. This impacts the fungal cell membrane, and how it is able to reproduce and adapt to stressors in its environment. [82]

Insecticidal properties

Capsaicin deters insects in multiple ways. The first is by deterring insects from laying their eggs on the pepper due to the effects capsaicin has on these insects. [83] Capsaicin can cause intestinal dysplasia upon ingestion, disrupting insect metabolism and causing damage to cell membranes within the insect. [84] [85] This in turn disrupts the standard feeding response of insects.

Seed dispersion and deterrents against granivorous mammals

Granivorous mammals pose a risk to the propagation of chilies because their molars grind the seeds of chilies, rendering them unable to grow into new chili plants. [86] [8] As a result, modern chilies evolved defense mechanisms to mitigate the risk of granivorous mammals. While capsaicin is present at some level in every part of the pepper, the chemical has its highest concentration in the tissue near the seeds within chilies. [7] Birds are able to eat chilies, then disperse the seeds in their excrement, enabling propagation. [8]

Adaptation to varying moisture levels

Capsaicin is a potent defense mechanism for chilies, but it does come at a cost. Varying levels of capsaicin in chilies currently appear to be caused by an evolutionary split between surviving in dry environments, and having defense mechanisms against fungal growth, insects, and granivorous mammals. [87] Capsaicin synthesis in chilies places a strain on their water resources. [88] This directly affects their fitness, as it has been observed that standard concentration of capsaicin of peppers in high moisture environments in the seeds and pericarps of the peppers reduced the seeds production by 50%. [89]

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">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, also spelled chile or chilli, 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 that give chili peppers their intensity when ingested or applied topically. Chili peppers exhibit a range of heat and flavors. This diversity is the reason behind the availability of different types of paprika and chili powder, each offering its own 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 25–38 mm wide, and hangs down from the plant. The pungency of jalapeño peppers varies, but is usually between 4,000 and 8,500 units on the Scoville scale. 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.

<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, grove 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.

<i>Capsicum annuum</i> Species of flowering plant in the nightshade family

Capsicum annuum, commonly known as paprika, chili pepper, red pepper, sweet pepper, jalapeño, cayenne, or bell pepper, is a fruiting plant from the family Solanaceae (nightshades), within the genus Capsicum which is native to the northern regions of South America and to southwestern North America. The plant produces berries of many colors including red, green, and yellow, often with pungent taste. It is also one of the oldest cultivated crops, with domestication dating back to around 6,000 years ago in regions of Mexico. The genus Capsicum has over 30 species but Capsicum annuum is the primary species in its genus, as it has been widely cultivated for human consumption for a substantial amount of time and has spread across the world. This species has many uses in culinary applications, medicine, self defense, and can even be ornamental.

<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).

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 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.

<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">Poblano</span> Mild chili pepper originating in Puebla, Mexico

The poblano is a mild chili pepper originating in Puebla, Mexico. Dried, it is called ancho or chile ancho, from the Spanish word ancho (wide). Stuffed fresh and roasted, it is popular in chiles rellenos poblanos.

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

Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge, a cactus-like plant commonly found in Morocco, and in Euphorbia poissonii found in northern Nigeria. It is a potent functional analog of capsaicin, the active ingredient in chili peppers.

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.

Capsinoids are non-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">Pungency</span> Sharp smell or flavor

Pungency refers to the taste of food commonly referred to as spiciness, hotness or heat, found in foods such as chili peppers. Highly pungent tastes may be experienced as unpleasant. The term piquancy is sometimes applied to foods with a lower degree of pungency that are "agreeably stimulating to the palate". Examples of piquant food include mustard and curry. The primary substances responsible for pungent taste are capsaicin, piperine and allyl isothiocyanate.

<span class="mw-page-title-main">Padrón pepper</span> Variety of pepper from Padrón, Spain

Padrón pepper, also called Herbón pepper, is a landrace variety of pepper from the municipality of Padrón in northwestern Spain.

<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 edible fruit, which are generally known as "peppers" or "capsicum". Sweet or bell peppers and some chili peppers belong to the Capsicum annuum species, making it the most cultivated species from the genus.

<span class="mw-page-title-main">Paprika</span> Spice made from red peppers

Paprika is a spice made from dried and ground red peppers. It is traditionally made from Capsicum annuum varietals in the Longum group, including chili peppers. Paprika can have varying levels of heat, but the chili peppers used for hot paprika tend to be milder and have thinner flesh than those used to produce chili powder. In some languages, but not English, the word paprika also refers to the plant and the fruit from which the spice is made, as well as to peppers in the Grossum group.

References

  1. ↑ "Capsaicin". ChemSpider, Royal Society of Chemistry, Cambridge, UK. 2018. Retrieved 9 June 2018.
  2. 1 2 3 4 5 6 7 "Capsaicin". PubChem, US National Library of Medicine. 27 May 2023. Retrieved 1 June 2023.
  3. ↑ "Qutenza- capsaicin kit". DailyMed. 10 January 2023. Retrieved 22 February 2023.
  4. ↑ "Drug Approval Package: Qutenza (capsaicin) NDA #022395". U.S. Food and Drug Administration (FDA). 3 October 2013. Retrieved 22 February 2023.
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  45. ↑ In a series of articles, J. C. Thresh obtained capsaicin in almost pure form:
    • Thresh JC (1876). "Isolation of capsaicin". The Pharmaceutical Journal and Transactions. 3rd Series. 6: 941–947.
    • Thresh JC (8 July 1876). "Capsaicin, the active principle in Capsicum fruits". The Pharmaceutical Journal and Transactions. 3rd Series. 7 (315): 21. [Note: This article is summarized in: "Capsaicin, the active principle in Capsicum fruits". The Analyst. 1 (8): 148–149. 1876. Bibcode:1876Ana.....1..148.. doi:10.1039/an876010148b.
    • Year Book of Pharmacy… (1876), pages 250 and 543;
    • Thresh JC (1877). "Note on Capsaicin". Year Book of Pharmacy: 24–25.
    • Thresh JC (1877). "Report on the active principle of Cayenne pepper". Year Book of Pharmacy: 485–488.
  46. ↑ Obituary notice of J. C. Thresh: "John Clough Thresh, M.D., D.Sc., D.P.H". British Medical Journal. 1 (3726): 1057–1058. June 1932. doi:10.1136/bmj.1.3726.1057-c. PMC   2521090 . PMID   20776886.
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Notes

  1. ↑ History of early research on capsaicin:
    1. Maurach B (1816). "Pharmaceutisch-chemische Untersuchung des spanischen Pfeffers" [Pharmaceutical-chemical investigation of Spanish peppers]. Berlinisches Jahrbuch für die Pharmacie (in German). 17: 63–73. Abstracts of Maurach's paper appear in: (i) Repertorium für die Pharmacie, vol. 6, page 117-119 (1819); (ii) Allgemeine Literatur-Zeitung, vol. 4, no. 18, page 146 (February 1821); (iii) "Spanischer oder indischer Pfeffer", System der Materia medica ..., vol. 6, pages 381–386 (1821) (this reference also contains an abstract of Bucholz's analysis of peppers).
    2. Henri Braconnot, French chemist Braconnot H (1817). "Examen chemique du Piment, de son principe âcre, et de celui des plantes de la famille des renonculacées" [Chemical investigation of the chili pepper, of its pungent principle [constituent, component], and of that of plants of the family Ranunculus]. Annales de Chimie et de Physique (in French). 6: 122- 131.
    3. Johann Georg Forchhammer, Danish geologist Oersted HC (1820). "Sur la découverte de deux nouveaux alcalis végétaux" [On the discovery of two new plant alkalis]. Journal de physique, de chemie, d'histoire naturelle et des arts[Journal of Physics, Chemistry, Natural History and the Arts] (in French). 90: 173–174.
    4. Ernst Witting, German apothecary Witting E (1822). "Considerations sur les bases vegetales en general, sous le point de vue pharmaceutique et descriptif de deux substances, la capsicine et la nicotianine" [Thoughts on the plant bases in general from a pharmaceutical viewpoint, and description of two substances, capsicin and nicotine]. Beiträge für die Pharmaceutische und Analytische Chemie[Contributions to Pharmaceutical and Analytical Chemistry] (in French). 3: 43. He called it "capsicin", after the genus Capsicum from which it was extracted. John Clough Thresh (1850–1932), who had isolated capsaicin in almost pure form, [45] [46] gave it the name "capsaicin" in 1876. [47] Karl Micko isolated capsaicin in its pure form in 1898. [48] [49] Capsaicin's chemical composition was first determined in 1919 by E. K. Nelson, who also partially elucidated capsaicin's chemical structure. [50] Capsaicin was first synthesized in 1930 by Ernst Spath and Stephen F. Darling. [51] In 1961, similar substances were isolated from chili peppers by the Japanese chemists S. Kosuge and Y. Inagaki, who named them capsaicinoids. [52] [53]

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