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Capsaicin

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Capsaicin
Capsaicin.png320px-Capsaicin-3D-vdW.png
General
Systematic name N-(4-hydroxy-3-methoxybenzyl)-
8-methylnon-trans-6-enamide
Other names (E)-N-(4-Hydroxy-3-methoxybenzyl)

-8-methylnon-6-enamide,
trans-8-Methyl-N-vanillylnon -6-enamide,
(E)-Capsaicin, CPS, C

Molecular formula C18H27NO3
SMILES OC1=C(C=C(C=C1)CNC
(=O)CCCC/C=C/C(C)C)OC
Molar mass Molar mass::305.41 g/mol
Appearance white or light yellow acicular crystals
CAS number CAS number::404-86-4
Properties
phase solid
Solubility in water

10.3 mg/L at 25 °C

Melting point Melting point::63 °C
Boiling point Boiling point::215 °C
Hazards
MSDS Material safety data sheet
Main hazards Toxic
NFPA 704

NFPA 704 svg.png

1
2
0
Flash point 263.1 °C
R/S statement R: R24/25
S: S26, S36/37/39, S45

Capsaicin is an organic compound perhaps best known for causing the prolonging burning sensation encountered when eating chili peppers. It is used for many different things like pest repellent, fighting cancer or even to lose weight. The Mayans used the intensity of capsaicin to their advantage during battle by throwing gourds filled with extract from peppers through the air. Today, it is used in a chemical weapon known as pepper spray. [1] Chili peppers come across as hot because capsaicin lets calcium ions enter the cell membrane, this action makes the pain known and it is sent to the next cell.Taking in a lot of capsaicin produces endorphins, this makes the spiciness more pleasurable and can even be addicting to some people.

Properties

This is a picture of chili peppers, where capsaicin is most active.

Capsaicin is the spicy and heated part of chili peppers. It is made of seven related alkaloid or capsaicinoids. Three of the seven mechanisms cause somewhat of a bite toward the back of the throat and two other components cause the prolonged burn on the tongue. This compound is insoluble in water, odorless, and tasteless. This chemical compound is found and created in the white veins of the chili pepper pod.Cite error: Invalid <ref> tag; invalid names, e.g. too many Capsaicin's molecular weight is the highest compared to most vanilloids. Even though this shocking liquid contains only 10 parts to the million, Capsaicin is still very noticeable in foods because of it's overwhelming, spicy flavor. This molecule has a very long hydrocarbon tail, which has the fiery flavor. The plumpy tail lets it move through cell membranes that are rich with lipids, this causes the burning sensation to be more intense and last longer. Some people may wonder why some chilies burn in their mouth when some burn in the throat. This is because there are some compounds like capsaicin found in chilies that contain some structural differences in the hydrocarbon tail. This changes their ability to fasten to the receptors and go through layers of receptors on the throat, tongue and mouth[1].

History

Above are baskets of peppers that contain capsaicin.

Chili peppers, where capsaicin is found, are native to Central and South America. A long time ago, around 7500 B.C., there is proof that shows that chili peppers were eaten regularly. In the 16th century, Portuguese and Spanish explorers brought these peppers into South Asia. From that time on, chili peppers became more and more popular. In the beginning, they were used for flavoring food and as a medicine for the natives and in warfare. Some people even used it to get rid of pests. Capsaicin seeds were spread by birds which were not affected by the drastic spice.[2] Christian Friedrich Bucholz isolated the most vigorous ingredient in chili peppers in 1816. Capsaicin was purified for the first time in 1846 by John Thresh. Up until 1919, the chemical structure was not known and it was named after the group Capsicum.[3]A chemist, Wilbur Scoville, developed a method to measure the exact level of heat of chilies in 1912. Scoville blended a sugar-water solution with a pure ground chilies. A panel of testers tested the solution until they reached the point where the solutions didn't burn the mouth any longer. A number was given to each according on how much water needed to be added before you couldn't taste the heat. This measurement of the many drops of sugar and water is converted to Scoville Heat Units. Much better versions of this test have been created since 1912 and it was named the Scoville Organoleptic Test.Cite error: Invalid <ref> tag; invalid names, e.g. too many

Uses

Prometheous Springs, a drink that contains a healthy dose of capsaicin.

Capsaicin can be used as a warming instrument on skin. It is combined with castor oil to help relieve joint pain caused by arthritis. It is also the main ingredient in pepper spray, which is used for security purposes all around the world. Believe it or not, capsaicin is also used for joint relief in horses. During the 2008 Beijing Olympics, the substance was found in four very successful horses so they banned it from equestrian sports.[2] Capsaicin is used to repel pests like voles, deer, skunks, raccoons, cats, dogs, rabbits, and squirrels. It is also used on vegetation such as crops and trees, garbage containers and buildings. Capsaicin is used as an attack prevention for dogs and bears.[4] Capsaicin can be used on the skin as a cream to relieve pain, the pain may increase but it soon decreases after the first use. When applied to the skin, it could relieve pain from skin conditions, joint problems, mouth sores, headaches, nervous system, pain disorders and pain after a surgery. If capsaicin is included in your eating habits, it can help the digestive system and stop diarrhea. Some people use it to loosen mucus from the lungs and it can help prevent heart disease, lower blood sugar, and cholesterol. Capsaicin is also used as an antioxidant and protects the body from bacterial infections.Cite error: Invalid <ref> tag; invalid names, e.g. too manyIt can be found as a gel, lotion, stick, cream, ointment, pad, or lotion. Capsaicin has many brand names including Icy Hot Arthritis Therapy, Zostrix, Arthricare for Women, and Capsagel. There is a lot of pain associated with osteoarthritis, rheumatoid arthritis, and diabetic neuropathy, capsaicin can help with any of these. Although it may seem like you need a prescription for capsaicin, capsaicin is available over the counter at most pharmacies. It can be used as a pain relief for arthritis but the relief is not immediate[5] Capsaicin is also known to help prevent gaining weight by killing fat cells. People who eat Thai or Indian food on a regular basis take in the most capsaicin because of the high level of capsaicin that is present in a lot of the food. It is even used to fight cancer because it endorses the regular series of cell death, this is called apoptosis.[6]

Side Effects

Some people may have an allergic reaction to capsaicin. Ulcers may occur if too much capsaicin is taken, but it is very rare.Cite error: Invalid <ref> tag; invalid names, e.g. too many Capsaicin has some common side effects, but they may vary for different people. Most people get a stinging sensation after using the cream form of capsaicin, but it should go away after a few days. There also more rare side effects that happen to be a lot more serious. Such as, blistering, redness, difficulty swallowing, or breathing, and irritation[7]. If using a topical capsaicin, some possible side effects would be cough, sore throat, stuffy or runny nose, tightness of the chest. Some less common side effects include: headache, pounding in the ears, blurred sight, and dizziness. By talking to your doctor, it is possible to try and prevent some of these side effects.[8]

References

  1. 1.0 1.1 Senese, Fred. Fire and Spice General Chemistry Online'. Web. January 26, 2012 (or access).
  2. 2.0 2.1 Unknown. The Strange, Pain-Relieving History of Capsaicin Castiva. Web. January 18, 2012 (or access).
  3. Liddell, Amy. Discovery of Capsaicin LiveStrong.com. Web. January 28, 2012 (or access).
  4. Gervais, J. A. Capsaicin Technical Fact Sheet Nation Pesticide Information Center. Web. January 28, 2012 (or access).
  5. Eustice, Carol. Capsaicin - 10 Things You Should Know About.com. Web. January 28, 2012 (or access).
  6. Whitney, M.T. Capsaicin from chili peppers may help prevent obesity, weight gain NaturalNews.com. Web. January 29, 2012 (or access).
  7. Unknown. Capsaicin Side Effects Drugs.com. Web. January 28, 2012 (or access).
  8. Unknown. Capsaicin (Topical Route) Mayo Clinic. Web. January 18, 2012 (or access).