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****** Menthol Background ******

 Laevo- or (-)-menthol is one of the most important flavoring chemicals. Menthol is used extensively in pharmaceuticals, cosmetics, toothpastes, chewing gum, and other toilet goods as well as in cigarettes. The current annual world production is estimated to be in excess of 19,000 metric tons.

The majority of (-)-menthol is obtained by freezing the oil of Mentha arvensis to crystallize the menthol present. This "natural" menthol is then physically separated by centrifuging the supernatant liquid (called dementholized cornmint oil) away from the menthol crystals. Any residual impurities are due to traces of Mentha arvensis oil, and these often impart a slight peppermint aroma to the menthol crystals.

 Considerable effort has been devoted to the production of (-)-menthol by synthetic or seini-synthetic means from other more readily available raw materials. Historically, the price of naturally derived (-)-menthol has fluctuated widely. This situation is now buffered to a degree by the two major comercial synthetic sources of (-)-menthol (Symrise and Takasago). However as the production of menthol in India continues to soar --- and raw material costs continue to increase for the synthetic producers, it appears that India will continue to increase market share with increasing margin pressure on Symrise & Takasago.

In 2007, Clark4 estimated the world production of natural menthol at 12,870 metric tons and synthetic menthol at 6,300 metric tons for a total of 19,170 metric tons. Although, the exact production in each area are rough estimates, the producing exporting sources are estimated to be:

Source (2007)
Metric Tons

India (natural)

9,700

China (natural)

2,120

Symrise (synthetic)

3,600

Takasago (synthetic)

1,500

Other synthetic*

1,200

Brazil (natural)**

..450

Taiwan (natural)**

..300

Japan (natural)**

..300

Total

19,170

*Other (synthetic) produced primarily from reduction of menthone ex Mentha arvensis oil primarily from India - may possibly be blended into natural menthol, in some cases.

** Primarily produced from crude menthol and/or Mentha arvensis oil from India or China

In 2007, worldwide consumption of (-)-menthol, by product area, was estimated to be4:

Oral hygiene

28.0%

Pharmaceuticals

26.6%

Tobacco

25.3%

Confectionaries

11.0%

Shaving products

7.0%

Miscellaneous

2.1%

In 1998, Clark5 estimated the world production of menthol at 11,800 metric tons. Although, the exact production in each area are rough estimates, the producing exporting sources are estimated to be:

Source (1998)
Metric Tons

India

5,630

China

2,500

Haarmann & Reimer

1,450

Takasago

.. 950

Others

..770

Brazil/Paraguay

..500

Total

11,800

In 1992, the major producing exporting sources were estimated to be:

Source (1992)

Metric Tons

China

2,300

Haarmann & Reimer

1,600

India

..750

Takasago

..650

Others

..650

Brazil/Paraguay

..350

Total

6,300

Figures on this page are adapted from information in references 2 & 3 found below.

References

1. Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974

2. Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993).

3. Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

4. Clark, G.S., Aroma Chemical Profile: Menthol, Perfumer & Flavorist, Vol. 32 (12), 38-47 (2007).

5. Clark, G.S., Menthol, Perfumer & Flavorist, Vol. 23 (5), 33-46 (1998).

 

 

 

 

 

Menthol Background & 

Menthol Enantiomers - Organoleptic Properties


The absolute configuration number nomeclature in the chart above follows that of IUPAC rules. However, much of the earlier literature for the menthol isomers used that of the p-Menthane numbering system. Both naming conventions are valid. The table below shows both ways.

IUPAC Numbering
p-Menthane Numbering

(1R,2R,5R)-(+)-NeoisoMenthol = (1R,2R,5R)-(+)- 2-Isopropyl-5-methylcyclohexanol

(1R,3R,4R)-(+)-NeoisoMenthol = (1R,3R,4R)-(+)-p-Menthan-3-ol

(1S,2R,5R)-(+)-IsoMenthol = (1S,2R,5R)-(+)-2-isopropyl-5-methylcyclohexanol

(1R,3S,4R)-(+)-IsoMenthol = (1R,3S,4R)-(+)-p-Menthan-3-ol

(1S,2S,5R)-(+)-NeoMenthol = (1S,2S,5R)-(+)-2-isopropyl-5-methylcyclohexanol

(1R,3S,4S)-(+)-NeoMenthol = (1R,3S,4S)-(+)-p-Menthan-3-ol

(1R,2S,5R)-(-)-Menthol = (1R,2S,5R)-(-)-2-isopropyl-5-methylcyclohexanol

(1R,2R,4S)-(-)-Menthol = (1R,2S,5R)-(-)-p-Menthan-3-ol

(1S,2S,5S)-(-)- NeoisoMenthol = (1S,2S,5S)-(-) -2-isopropyl-5-methylcyclohexanol

(1S,3S,4S)-(-)-NeoisoMenthol = (1S,3S,4S)-(-)-p-Menthan-3-ol

(1R,2S,5S)-(-)-Isomenthol = (1R,2S,5S)-(-)-2-isopropyl-5-methylcyclohexanol

(1S,3R,4S)-(-)-Isomenthol = (1S,3R,4S)-(-)-p-Menthan-3-ol

(1R,2R,5S)-(-)-NeoMenthol = (1R,2R,5S)-(-)-2-isopropyl-5-methylcyclohexanol

(1S,3R,4R)-(-)-NeoMenthol = (1S,3R,4R)-(-)-p-Menthan-3-ol

(1S,2R,5S)-(+)-Menthol = (1S,2R,5S)-(+)-2-isopropyl-5-methylcyclohexanol

(1S,3S,4R)-(+)-Menthol = (1S,3S,4R)-(+)-p-Menthan-3-ol

 

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Menthol - Page 1 (Background & Organoleptic Propertites)
H&R (-)-Menthol Synthesis from m-Cresol / Thymol
Takasago (-)-Menthol Synthesis from Myrcene
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Synthesis of (-)-Menthol from (+)-Citronellal
Synthesis of (-)-Menthol from (+)-Pulegone
Synthesis of (-)-Menthol from (-)-Piperitone
SCM-GLIDCO (-)Menthol Synthesis from (-)-beta-Phellandrene
(-)-Menthol Synthesis from (-)-delta-3-Carene
(-)-Menthol Synthesis from (+)-Limonene
(-)-Menthol Synthesis from (-)-beta-Pinene
(-)-Menthol via Lipase Resolution
(-)-Menthol from Mesityl oxide via Piperitenone

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