1. Menthol
Marco Casanova
John Ceballos
CHM 2210
December 03, 2010
John 1

2. Chemical Properties Chemical Formula: C10H20O IUPAC Name:
(1R,2S,5R)-2-Isopropyl-5-Methylcyclohexanol
Molar Mass: g/mol
Density: g  cm-3
Marco 2

3. Chemical Properties Boiling Point: 212 °C Melting Point: 36-38 °C
Solid at room temperature
Waxy, crystalline substance
Clear or White in color
John 3

4. Medicinal Uses
Marco
Digestive Tract………The menthol in peppermint.. Also stimulates the production of bile
Hot cup of tea, great way to settle the stomach after a big meal. n
Used very often as a flavoring agent
Chewing gum, candy
Menthol Vapors are famous for relieving nasal, sinus and chest congestion.
Also, the steam from the same tea that you made to soothe your digestive tract, will relieve some congestion
Vicks Vaporub, Mentholatum
Antipruritic to releve itching
Topical Analgesic to relieve minor aches and pains such as muscle cramps, sprains & headaches
Icy Hot, Tiger Balm & Knee/elbow sleeves
In certain medications to treat sunburns
Cooling sensation (often associated w/ aloe)
Found in chloroform sprays for the relief of localized pain 4

5. Products Found In
In cigarettes for flavor and to reduce throat and sinus irritation caused by smoking
Ricqles contains 80% alcohol and is used to alleviate nausea, in particular motion sickness.
Achieved by pouring a few drops on a lump of sugar.
In Japan, they sell fever reducing patches that children would put on their forehead to achieve a cooling feeling.
Excellent breath freshener
Increase effectiveness by adding anise, caraway or cinnamo 5

6. Cooling effects Binds to the TRPM8 receptor TRPM8 receptor ≈ 8-28°C
Na+ & Ca+ flow into cell
Causes electrical change in cell
Brain registers cool
John 6

7. Structural Isomers
John
What do + and – mean? Significance? 7

8. Naturally Occurring Isomers
The Isopropyl must always be in the trans orientation to both the methyl and hydroxyl groups.
All of these representations are correct!
Notice how all three bulky groups are in the equatorial position, making (-)Menthol and it’s enantiomer the two moststable isomers out of the eight. 8

9. Synthesis
Marco
As is the case w/ many widely used natural products, the demand for menthol greatly exceeds the natural supply.
Manufactured as a single enantiomer (94%) on the scale of 3,000 tons per year by takasago International Corporation.
Developed by a team that is led by Ryoji Noyori.
Know if the compound is e or z in each compound 9

10. Possible Reactions From Menthol
Marco
Menthone
Has been oxidized by Chromium Trioxide
Oxidation an also be achieved by using other oxidizing agents such as Chromic acid or dichromate
Bottom Left
Oxidation has caused the ring to break open
3-Menthene
Can be easily dehydrated to achieve 3-Menthene
This H2SO4 is 2% Sulfuric Acid
CrO3 = Chromium Trioxide
CH3COOH = Acetic Acid
PCL5 = Phosphorus Pentachloride
Substitution
Which is stronger? Dil H2SO4 or H2SO4
Remember to look up what it means for a compound to undergo oxidation?!? 10

11. References
Cotton, Simon.”Menthol”2006http:// nthol/mentholh.htm
Harringson, Karl.”Menthol”.3dchem.2005http:// cules.asp?ID=202
Leffingwell, John P.H.D.”cool without menthol”Leffingwell and associates.2010http:// enthol.htm
Foster, Nicki. “What is menthol”.WiseGeek.2010http:// is-menthol.htm 11

12. Acknowledgments Marco Casanova John Ceballos Cary Pellizzeri
Professor Renee Becker
last 12