Difference between revisions of "Menthol"
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(Created page with "{{Chembox | Name = Menthol | Reference = | IUPACName = (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol | PIN = | SystematicName = | OtherNames = 3-p-Menthanol<br>5-methyl-2-(1-met...") |
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| HenryConstant = | | HenryConstant = | ||
| LogP = | | LogP = | ||
| − | | MolarMass = | + | | MolarMass = 156.27 g/mol |
| MeltingPt = | | MeltingPt = | ||
| MeltingPtC = 36-38 | | MeltingPtC = 36-38 | ||
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| pKa = | | pKa = | ||
| pKb = | | pKb = | ||
| − | | Solubility = | + | | Solubility = 1.35799 g/100 ml (at 25 °C)<ref>Ajisaka; Hara; Mikuni; Hashimoto; Bioscience, biotechnology, and biochemistry; vol. 64; nb. 4; (2000); p. 731 - 734</ref> |
| − | | SolubleOther = | + | | SolubleOther = Soluble in glacial [[acetic acid]], [[chloroform]], [[diethyl ether]], anhydrous [[ethanol]], [[hexane]], [[petroleum ether]]<br>Slightly soluble in [[methanol]] |
| − | | | + | | Solubility1 = 0.1 g/100 ml |
| − | | VaporPressure = | + | | Solvent1 = methanol |
| + | | VaporPressure = 7.67x10<sup>-3</sup> mmHg at 25 °C | ||
}} | }} | ||
| Section3 = {{Chembox Structure | | Section3 = {{Chembox Structure | ||
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}} | }} | ||
}} | }} | ||
| − | '''Menthol''' is an organic compound, found in various plants, such as peppermint, widely used in medicine and in food industry. Menthol | + | '''Menthol''' is an organic compound, found in various plants, such as peppermint, widely used in medicine and in food industry. Menthol is available as several isomers, with the '''(−)-menthol''' enantiomer form being the most common form in nature. |
==Properties== | ==Properties== | ||
| Line 114: | Line 115: | ||
===Physical=== | ===Physical=== | ||
| − | Menthol is a colorless, waxy crystalline solid at room temperature, with a strong pleasant smell. It is | + | Menthol is a colorless, waxy crystalline solid at room temperature, with a strong pleasant smell. It is slightly soluble in water, but more so in organic solvents. There are many different values for the water solubility in literature, mostly due to the different racemic composition, as well as traces of other organic contaminants. Is is also soluble in glacial [[acetic acid]], [[chloroform]], [[diethyl ether]], anhydrous [[ethanol]], [[methanol]] (100 mg/ml), [[petroleum ether]]. |
==Availability== | ==Availability== | ||
Menthol is sold by various chemical suppliers, and is available either as racemic mixture or as individual isomers. | Menthol is sold by various chemical suppliers, and is available either as racemic mixture or as individual isomers. | ||
| − | Menthol is also sold in various pharmacies as an alcoholic solution, as a weak local anesthetic and counterirritant. | + | Menthol is also sold in various pharmacies as an alcoholic solution, as a weak local anesthetic and counterirritant. It is also sold by soap and natural product companies, in pure crystalline form. |
Menthol can be extracted form various plants, such as peppermint, though you will need a large amount of plant material to obtain useful quantities of menthol. | Menthol can be extracted form various plants, such as peppermint, though you will need a large amount of plant material to obtain useful quantities of menthol. | ||
| Line 129: | Line 130: | ||
*Make beautiful large crystals | *Make beautiful large crystals | ||
*Make an air freshener | *Make an air freshener | ||
| + | *Make [[sodium]] metal | ||
==Handling== | ==Handling== | ||
| Line 142: | Line 144: | ||
==References== | ==References== | ||
<references/> | <references/> | ||
| + | ===Sciencemadness Library=== | ||
| + | *[http://library.sciencemadness.org/library/books/the_chemistry_of_essential_oils_and_artificial_perfumes_i.pdf The Chemistry of essential oils and perfumes vol I, by Ernest J. Parry, 1921] | ||
| + | *[http://library.sciencemadness.org/library/books/the_chemistry_of_essential_oils_and_artificial_perfumes_ii.pdf The Chemistry of essential oils and perfumes vol II, by Ernest J. Parry, 1922] | ||
| + | |||
===Relevant Sciencemadness threads=== | ===Relevant Sciencemadness threads=== | ||
*[http://www.sciencemadness.org/talk/viewthread.php?tid=16977 Menthol extraction from peppermint] | *[http://www.sciencemadness.org/talk/viewthread.php?tid=16977 Menthol extraction from peppermint] | ||
*[http://www.sciencemadness.org/talk/viewthread.php?tid=10606 menthol extraction] | *[http://www.sciencemadness.org/talk/viewthread.php?tid=10606 menthol extraction] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=155198 Use For Menthol?] | ||
[[Category:Chemical compounds]] | [[Category:Chemical compounds]] | ||
| Line 151: | Line 158: | ||
[[Category:Biologically-derived compounds]] | [[Category:Biologically-derived compounds]] | ||
[[Category:Materials available as food grade]] | [[Category:Materials available as food grade]] | ||
| + | [[Category:Fragrant compounds]] | ||
Latest revision as of 08:55, 5 August 2021
| |
| Names | |
|---|---|
| IUPAC name
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
| |
| Other names
3-p-Menthanol
5-methyl-2-(1-methylethyl)cyclohexanol Hexahydrothymol Menthomenthol Peppermint camphor | |
| Identifiers | |
| Jmol-3D images | Image |
| |
| Properties | |
| C10H20O | |
| Molar mass | 156.27 g/mol |
| Density | 0.890 g/cm3 (racemic or (−)-isomer) |
| Melting point | 36–38 °C (97–100 °F; 309–311 K) racemic 42–45°C, (-)-isomer, α crystalline form |
| Boiling point | 212 °C (414 °F; 485 K) |
| 1.35799 g/100 ml (at 25 °C)[1] | |
| Solubility | Soluble in glacial acetic acid, chloroform, diethyl ether, anhydrous ethanol, hexane, petroleum ether Slightly soluble in methanol |
| Solubility in methanol | 0.1 g/100 ml |
| Vapor pressure | 7.67x10-3 mmHg at 25 °C |
| Hazards | |
| Safety data sheet | ScienceLab |
| Flash point | 93 °C |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Menthol is an organic compound, found in various plants, such as peppermint, widely used in medicine and in food industry. Menthol is available as several isomers, with the (−)-menthol enantiomer form being the most common form in nature.
Contents
Properties
Chemical
Menthol can be oxidized with chromium trioxide to menthone. Diluted sulfuric acid dehydrates menthol to 3-menthene.
Physical
Menthol is a colorless, waxy crystalline solid at room temperature, with a strong pleasant smell. It is slightly soluble in water, but more so in organic solvents. There are many different values for the water solubility in literature, mostly due to the different racemic composition, as well as traces of other organic contaminants. Is is also soluble in glacial acetic acid, chloroform, diethyl ether, anhydrous ethanol, methanol (100 mg/ml), petroleum ether.
Availability
Menthol is sold by various chemical suppliers, and is available either as racemic mixture or as individual isomers.
Menthol is also sold in various pharmacies as an alcoholic solution, as a weak local anesthetic and counterirritant. It is also sold by soap and natural product companies, in pure crystalline form.
Menthol can be extracted form various plants, such as peppermint, though you will need a large amount of plant material to obtain useful quantities of menthol.
Preparation
Synthesizing menthol is a long and costly process, and you're better off extracting it from peppermint.
Projects
- Make beautiful large crystals
- Make an air freshener
- Make sodium metal
Handling
Safety
Menthol has low toxicity when inhaled, though it's best to avoid consuming large quantities of it.
Storage
Menthol should be stored in closed bottles, at temperatures lower than 35-40 °C. It can also be stored in the fridge.
Disposal
Menthol has low toxicity and can be poured down the drain, dumped in trash or poured in the soil.
References
- ↑ Ajisaka; Hara; Mikuni; Hashimoto; Bioscience, biotechnology, and biochemistry; vol. 64; nb. 4; (2000); p. 731 - 734
Sciencemadness Library
- The Chemistry of essential oils and perfumes vol I, by Ernest J. Parry, 1921
- The Chemistry of essential oils and perfumes vol II, by Ernest J. Parry, 1922
Relevant Sciencemadness threads
Categories:
- Chemical pages without CAS Registry Number
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Articles containing unverified chemical infoboxes
- Chemical compounds
- Organic compounds
- Alcohols
- Biologically-derived compounds
- Materials available as food grade
- Fragrant compounds
