Capsaicin; The Power of Peppers

Ben Moore

Chemistry 496

What is Capsaicin?

HO

H3CO

H2C HN C

OH2C CH CH CH

CH3

CH34

MW 305.42 bp 210-220oC melt temp 65oC

N(4-hydroxy-3methoxybenzyl)-8methlnon-trans-6-enamide

Capsaicin has no taste or odor

It’s detectable at 16 ppm by humans

Used as an additive to analgesics

What are the Properties?

Capsaicin or Capcinoids

There are many capcinoids that make

peppers hot Capsaicin 69%, Dihydrocapsaicin

22%, Nordihydrocapsaicin 7%, Homocapsaicin

and Dihomocapsaicin each 1%.

How Do They Work?

Capcinoids are all in the vaniloid family

They stimulate nerve cells to increase the flow of calcium

In large amounts this can cause nerve damage and burns

Is it lethal? Not really LD50 estimates based on rats showA 150 pound person would have to eat 13 grams

How Hot is Too Hot

0-100 - most Bell/Sweet pepper varieties.

500-1000 - New Mexican peppers 1,000-1,500 - Espanola peppers 1,000-2,000 - Ancho Pasilla peppers 1,000-2,500 - Cascabel Cherry peppers 2,500-5,000 - Jalapeno Mirasol peppers 5,000-15,000 - Serrano peppers 15,000-30,000 - de Arbol peppers 30,000-50,000 - Cayenne Tabasco50,000-100,000 - Chiltepin peppers 100,000-350,000 - Scotch Bonnet Thai200,000 to 500,000 - Habanero peppers

Around 16,000,000 Scoville Units is Pure Capsaicin

Stopping the Burn

Soluble in alcohols, fats, oils

Drinking water just makes it worse

Industrial uses

Pepper spray of course!

Repellant for squirrels, dogs and cats.

Treats arthritis pain, psoriasis, shingles, has been shown to reduce cancerous growth.

Brand names include Therma Patch, Penecine and Zostrix.

References

http://www.fiery-foods.com/dave/capsaicin.asp

http://www.fiery-foods.com/dave/cap2000.html

http://student.biology.arizona.edu/honors98/group12/pepper.html

http://www.chem.ox.ak.uk/mom/capsaicin/capsaicin.html