Question

Day 1:

1. What is Oil wintergreen? Name the plant source for Oil of Wintergreen.
2. Draw the structure of the major component in Oil of Wintergreen.
3. Mention three biological activities of Oil of winter green.
4. Using REAXYS tool, find a synthetic protocol for the synthesis of ether derivative of Oil of Winter green.
5. List the starting materials and their quantities required to prepare the given ether derivative.
6. Write the mechanism involved in the proposed reaction.
7. Document the search including screen shots / pictures and submit for grading.

Day 2:

1. Propose a method to purify the synthesized ether derivative.
2. List the materials required for the purification and their quantities
3. Propose a method to estimate the purity of the synthesized ether derivative.
4. Document the search including screen shots / pictures and submit for grading.

Day 3:

1. Find a protocol to test the antioxidant activity of Oil of Wintergreen and its derivatives.
2. List the reagents and chemical required for the procedure. Include the quantities of the materials required.
3. Include equations, screen shots of your search in the pre lab report.

Answer 1

1. Wintergreen oil is a pale yellow or pinkish fluid liquid that is strongly aromatic with a sweet, woody odor (components: methyl salicylate (about 98%), α-pinene, myrcene, delta-3-carene, limonene, 3,7-guaiadiene, and delta-cadinene) that gives such plants a distinctive "medicinal" smell whenever bruised.

Wintergreen oil comes from a big plant source of methyl salicylate – wintergreen plants. Easily distilled from plant leaves, oil of wintergreen is 96-99% methyl salicylate and very pungent. Besides smelling minty, methyl salicylate also tastes minty, but wintergreens aren’t mints. Wintergreen plants are members of the genus Gaultheria, while mint plants like peppermint and spearmint, are of the genus Mentha.

2. Methyl Salicylate:

3. Wintergreen oil acts in a similar way as aspirin in that it can produce analgesic effect when topically applied on skin. It also shows antipyretic actions when the essence of wintergreen is mixed with alcohol. Is very effectual against intermittent fever. This can also be used to treat sexually transmitted disease as gonorrhea and in gonorrheal & other rheumatism. Wintergreen oil can be used for trigeminal neuralgia, and in subcutaneous and chronic cystitis.This oil is used as liniments and ointments for reliving pains in above mentioned cases.

4.  Aspirin (also known as acetyl salicylic acid) is in a group of drugs called salicylates. It works by reducing substances in the body that cause pain, fever, and inflammation. It is also known to treat mild to moderate pain, and also to reduce fever or inflammation. It is sometimes used to treat or prevent heart attacks, strokes, and angina.On the other hand, the oil of wintergreen or methyl salicylate also came from the same active ingredient, salicylic acid. Commercially, it is used as a flavoring for candies and chewing gum and in the treatment of muscular aches and pains. When synthesized and sold as the oil of wintergreen itself, it can be sold as beverage.The two compounds indicated are both organic esters. An ester is a compound that is formed when an acid (containing the COOH group) reacts with an alcohol (a compound containing an -OHgroup). In this experiment the experimenters will prepare two esters of o-hydroxy benzoic acid, more commonly known as salicylic acid. One of the esters, acetyl salicylic acid, is aspirin, the common analgesic. They will synthesize aspirin by mixing salicylic acid with acetic anhydride. The second ester product is oil of wintergreen, or methyl salicylate, which we prepare by allowing salicylic acid to react with methyl alcohol. This compound, which has a familiar odor, is used as a flavoring agent and in rubbing ointments.