Capsaicin

Capsaicin
Heat	Above peak
Scoville scale	15,000,000–16,000,000 SHU

Capsaicin
Names
	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
;
	[show]
	SMILES[show]
Properties
Chemical formula	C18H27NO3
Molar mass	305.42 g·mol−1
Appearance	crystalline white powder
Odor	highly volatile and 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
Solubility in water	0.0013 g/100 mL
Solubility	soluble in alcohol, ether, benzene; slightly soluble in CS2, HCl, petroleum
Vapor pressure	1.32×10−8 mm Hg at 25 °C
UV-vis (λmax)	280 nm
Structure
Crystal structure	monoclinic
Pharmacology
ATC code	M02AB01 (WHO) N01BX04 (WHO)
License data	EU EMA: by INN;
Hazards
Main hazards	Toxic (T)
Safety data sheet	Capsaicin, Natural MSDS
R-phrases(outdated)	R24/25
S-phrases(outdated)	S26, S36/37/39, S45
NFPA 704	1 2 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Capsaicin (/kæpˈseɪ.ɪsɪn/ (INN); 8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related compounds are called capsaicinoidsand are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi.^[3]Pure capsaicin is a hydrophobic, colorless, highly pungent,^[2] crystalline to waxy compound.

History[edit]

The compound was first extracted in impure form in 1816 by Christian Friedrich Bucholz (1770–1818).^[4] 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,^[5]^[6] gave it the name "capsaicin" in 1876.^[7] Karl Micko isolated capsaicin in its pure form in 1898.^[8]^[9] Capsaicin's chemical composition was first determined by E. K. Nelson in 1919, who also partially elucidated capsaicin's chemical structure.^[10] Capsaicin was first synthesized in 1930 by Ernst Spath and Stephen F. Darling.^[11] In 1961, similar substances were isolated from chili peppers by the Japanese chemists S. Kosuge and Y. Inagaki, who named them capsaicinoids.^[12]^[13]

In 1873 German pharmacologist Rudolf Buchheim^[14] (1820–1879) and in 1878 the Hungarian doctor Endre Hőgyes^[15]stated that "capsicol" (partially purified capsaicin^[16]) caused the burning feeling when in contact with mucous membranesand increased secretion of gastric acid.

Capsaicinoids[edit]

The most commonly occurring capsaicinoids are capsaicin (69%), dihydrocapsaicin (22%), nordihydrocapsaicin (7%), homocapsaicin (1%), and homodihydrocapsaicin (1%) ^[17]

Besides the five natural capsaicinoids (table below), one synthetic member of the capsaicinoid family exists: vanillylamide of n-nonanoic acid (VNA, also PAVA) used as a reference substance for determining the relative pungency of capsaicinoids.^{[citation needed]}

Capsaicinoid name	Abbrev.	Typical relative amount	Scoville heat units
Capsaicin	C	69%	16,000,000
Dihydrocapsaicin	DHC	22%	15,000,000
Nordihydrocapsaicin	NDHC	7%	9,100,000
Homodihydrocapsaicin	HDHC	1%	8,600,000
Homocapsaicin	HC	1%	8,600,000
Nonivamide	PAVA		9,200,000

Biosynthesis[edit]

History[edit]

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.^[18]^[19]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.,^[20]^[21] and Sukrasno and Yeoman.^[22] Suzuki et al. are responsible for identifying leucine as another precursor to the branched-chain fatty acid pathway.^[23] 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.^[24]

Biosynthetic pathway[edit]

Plants exclusively of the Capsicum genus produce capsaicinoids, which are alkaloids.^[25] 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.^[26]

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.^[27]^[28]^[29]^[30]

Capsaicin is the most abundant capsaicinoid found in the Capsicum genus, but at least ten other capsaicinoid variants exist.^[31] Phenylalanine supplies the precursor to the phenylpropanoid pathway while leucine or valine provide the precursor for the branched-chain fatty acid pathway.^[27]^[28] To produce capsaicin, 8-methyl-6-nonenoyl-CoA is produced by the branched-chain fatty acid pathway and condensed with vanillamine. Other capsaicinoids are produced by the condensation of vanillamine 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.^[32] All condensation reactions between the products of the phenylpropanoid and branched-chain fatty acid pathway are mediated by capsaicin synthase to produce the final capsacinoid product.^[27]^[28]

Vanillamine is a product of the phenylpropanoid pathway

Valine enters the branched fatty acid pathway to produce 8-methyl-6-nonenoyl-CoA

Capsaicin synthase condenses vanillamine and 8-methy-6-nonenoyl CoA to produce capsaicin

Natural function[edit]

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.^[33]

The seeds of Capsicum plants are dispersed predominantly by birds: in birds, the TRPV1 channel does not respond to capsaicin or related chemicals (avian vs. mammalian TRPV1 show functional diversity and selective sensitivity). 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.^[34] There is also evidence that capsaicin may have evolved as an anti-fungal agent:^[35] 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.

In 2006, it was discovered that the venom of a certain tarantula species activates the same pathway of pain as is activated by capsaicin; this was the first demonstrated case of such a shared pathway in both plant and animal anti-mammal defense.^[36]

Uses[edit]

Food[edit]

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 spice or "heat" (piquancy), usually in the form of spices such as chili powder and paprika.^[37]In high concentrations, capsaicin will also cause a burning effect on other sensitive areas, such as skin or eyes.^[38] The degree of heat found within a food is often measured on the Scoville scale.^[37] Because people enjoy the heat,^[37] there has long been a demand for capsaicin-spiced products like curry, chili con carne, and hot sauces such as Tabasco sauce and salsa.^[37]

It is common for people to experience pleasurable and even euphoric effects from ingesting capsaicin.^[37] Folklore among self-described "chiliheads" attributes this to pain-stimulated release of endorphins, a different mechanism from the local receptor overload that makes capsaicin effective as a topical analgesic.^[38]

Research and pharmaceutical use[edit]

Capsaicin is used as an analgesic in topical ointments, nasal sprays (Sinol-M), and dermal patches to relieve pain, typically in concentrations between 0.025% and 0.1%.^[39] 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.^[39]

It is also used to reduce the symptoms of peripheral neuropathy such as post-herpetic neuralgia caused by shingles.^[39]Capsaicin transdermal patch (Qutenza) for the management of this particular therapeutic indication (pain due to post-herpetic neuralgia) was approved as a therapeutic by the U.S. FDA,^[40] but a subsequent application for Qutenza to be used as an analgesic in HIV neuralgia was refused.^[41]

Although capsaicin creams have been used to treat psoriasis for reduction of itching,^[39]^[42]^[43] a review of six clinical trialsinvolving topical capsaicin for treatment of pruritus concluded there was insufficient evidence of effect.^[44]

There is insufficient clinical evidence to determine the role of ingested capsaicin on a variety of human disorders, including obesity, diabetes, cancer and cardiovascular diseases.^[39]

Pepper spray and pests[edit]

Capsaicin is also an active ingredient in riot control and personal defense pepper spray agents.^[45]^[46]^[47] When the spray comes in contact with skin, especially eyes or mucous membranes, it produces pain and breathing difficulty, discouraging protestors and assailants. Refer to the Scoville scale for a comparison of pepper spray to other sources of capsaicin.

Capsaicin is also used to deter pests, specifically mammalian pests. Targets of capsaicin repellants include voles, deer, rabbits, squirrels, bears, insects, and attacking dogs.^[48] Ground or crushed dried chili pods may be used in birdseed to deter rodents,^[49] taking advantage of the insensitivity of birds to capsaicin. The Elephant Pepper Development Trust claims the use of chili peppers to improve crop security for rural African communities^{[citation needed]}. Notably, an article published in the Journal of Environmental Science and Health 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."^[50]

The first pesticide product using solely capsaicin as the active ingredient was registered with the U.S. Department of Agriculture in 1962.^[48]

Equestrian sports[edit]

Capsaicin is a banned substance in equestrian sports because of its hypersensitizing and pain-relieving properties. At the show jumping events of the 2008 Summer Olympics, four horses tested positive for the substance, which resulted in disqualification.^[51]

Mechanism of action[edit]

The burning and painful sensations associated with capsaicin result from its chemical interaction with sensory neurons. Capsaicin, as a member of the vanilloid family, binds to a receptor called the vanilloid receptor subtype 1 (TRPV1).^[52] First cloned in 1997, TRPV1 is an ion channel-type receptor.^[53] TRPV1, which can also be stimulated with heat, protons and physical abrasion, permits cations to pass through the cell membrane when activated. The resulting depolarization of the neuron stimulates it to signal the brain. By binding to the TRPV1 receptor, the capsaicin molecule produces similar sensations to those of excessive heat or abrasive damage, explaining why the spiciness of capsaicin is described as a burning sensation.

Early research showed capsaicin to evoke a long-onset current in comparison to other chemical agonists, suggesting the involvement of a significant rate-limiting factor.^[54] Subsequent to this, the TRPV1 ion channel has been shown to be a member of the superfamily of TRP ion channels, and as such is now referred to as TRPV1. There are a number of different TRP ion channels that have been shown to be sensitive to different ranges of temperature and probably are responsible for our range of temperature sensation. Thus, capsaicin does not actually cause a chemical burn, or indeed any direct tissue damage at all, when chili peppers are the source of exposure. The inflammation resulting from exposure to capsaicin is believed to be the result of the body's reaction to nerve excitement. For example, the mode of action of capsaicin in inducing bronchoconstriction is thought to involve stimulation of C fibers^[55] culminating in the release of neuropeptides. In essence, the body inflames tissues as if it has undergone a burn or abrasion and the resulting inflammation can cause tissue damage in cases of extreme exposure, as is the case for many substances that cause the body to trigger an inflammatory response.

Toxicity[edit]

Acute health effects[edit]

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). LD₅₀ in mice is 47.2 mg/kg.^[56]^[57]

Painful exposures to capsaicin-containing peppers are among the most common plant-related exposures presented to poison centers.^[58] 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.^[59]

When used for weight loss in capsules, there has been a report of heart attack; this was thought to be due to excess sympathetic output.^[60]

Treatment after exposure[edit]

The primary treatment is removal from exposure. Contaminated clothing should be removed and placed in airtight bags to prevent secondary exposure.

For external exposure, bathing the mucous membrane surfaces that have contacted capsaicin with oily compounds such as vegetable oil, paraffin oil, petroleum jelly(Vaseline), creams, or polyethylene glycol is the most effective way to attenuate the associated discomfort;^{[citation needed]} since oil and capsaicin are both hydrophobic hydrocarbons the capsaicin that has not already been absorbed into tissues will be picked up into solution and easily removed. Capsaicin can also be washed off the skin using soap, shampoo, or other detergents. Plain water is ineffective at removing capsaicin,^[56] as are bleach, sodium metabisulfite and topical antacidsuspensions.^{[citation needed]} Capsaicin is soluble in alcohol, which can be used to clean contaminated items.^[56]

When capsaicin is ingested, cold milk is an effective way to relieve the burning sensation (due to caseins having a detergent effect on capsaicin^[61]); and room-temperature sugar solution (10%) at 20 °C (68 °F) is almost as effective.^[62] The burning sensation will slowly fade away over several hours if no actions are taken.

Capsaicin-induced asthma might be treated with oral antihistamines or corticosteroids.^[59]

Effects on weight loss and regain[edit]

There is no evidence showing that weight loss is directly correlated with ingesting capsaicin. Well-designed clinical studies have not been performed because the pungency of capsaicin in prescribed doses under research prevents subject compliance

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Pepper	Scoville Heat Units	Description
Cherry	500	Typically measures 4 inches long and 4 inches wide, with a shape that resembles a heart. The heat is very mild.
Anaheim	1,000 to 5,000	Maroon in color and has a long, skinny body. The flavor is only slightly hotter than the cherry variety.
Jalapeño	2,000 to 8,000	This pepper is usually red or green, with a length of 2 to 3 inches. Many people agree that it gives off the right amount of spiciness, leading to its popularity.
Serrano	10,000 to 25,000	The appearance is similar to the jalapeño, but with a hotter taste.
Cayenne	25,000 to 50,000	This pepper is popular for spicy food lovers because it adds a noticeable amount of heat.
Tabasco	30,000 to 60,000	This special type of pepper is used to produce the popular Tabasco hot sauce. A single pepper usually measures 2 inches long, and can come in green, red, yellow or orange.
Thai	50,000 to 100,000	Typically measuring less than an inch per pepper, Thai peppers pack serious heat. It’s mainly added to spicy Thai dishes.
Rocoto	100,000 to 250,000	The rocoto pepper has a large size similar to the bell pepper, but is rounder and only comes in red or green. It’s usually used to make special hot sauces.
Habanero	150,000 to 350,000	The habanero is well-known for being one of the spiciest peppers. It can come in various colors, and measures only 3 centimeters in length.
Ghost	1,000,000	Recognized as one of the hottest peppers in the market, a single seed from a ghost pepper can leave your mouth scorching for up to 30 minutes.

Pain Relief As mentioned previously, capsaicin may help relieve pain by exhausting your body’s supply of substance P, a chemical found in your nerve cells that plays a role in transmitting pain signals to your brain. In one study, heartburn sufferers were given 2.5 grams of red chili peppers per day. They noted that at the beginning of the treatment, pain slightly worsened, but gradually improved over time.12	Weight Management Spicy foods, quite literally, can help burn fat and help you lose weight. In a study published in the Journal of Nutritional Science and Vitaminology, participants were given 10 grams of red pepper during a meal. After eating, the researchers monitored the participants’ energy expenditure and learned that chili peppers increased it after consumption.13 It is believed that your body can burn an extra 50 calories per day if you consume capsaicin regularly.14
Reduce Hunger Several studies have shown that capsaicin may help reduce hunger, helping prevent overeating and excess weight gain.15,16,17,18 According to a study published in the European Journal of Nutrition, capsaicin works by reducing the production of ghrelin, the hormone responsible for triggering hunger.19	Blood Pressure Maintenance Capsaicin may help promote long-term heart health. According to one study, mice affected with high blood pressure experienced relief after they consumed food mixed with capsaicin. The researchers went on to suggest that capsaicin activates the transient receptor potential vanilloid 1 (TRPV1), which contributes to vasorelaxation and lowered blood pressure.20
Boost Digestive Health Aside from reducing hunger, capsaicin may help promote a well-functioning digestive tract. One study found that it enhanced the buffering component of gastric secretory responses and gastric emptying, as well as prevention of gastric mucosal damage from ethanol-based beverages.21 Another study suggested that capsaicin can help promote the healing of gastric ulcers by inhibiting acid secretion, as well as stimulating alkali and mucus production and gastric blood flow.22	May Lower the Risk of Cancer Capsaicin may have the ability to fight against cancer by attacking pathways in the growth of cancer cells. In a related study, capsaicin has been shown to induce apoptosis in prostate23 and in another study, breast cancer cells were tested.24

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