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Isopulegol

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Identification
Molecular formula
C10H18O
CAS number
89-79-2
IUPAC name
(1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanol
State
State

Isopulegol is a liquid at room temperature, typically used in the production of perfumes and flavors due to its aroma characteristics.

Melting point (Celsius)
-6.50
Melting point (Kelvin)
266.65
Boiling point (Celsius)
212.00
Boiling point (Kelvin)
485.15
General information
Molecular weight
156.27g/mol
Molar mass
156.2680g/mol
Density
0.9324g/cm3
Appearence

Isopulegol is a colorless liquid with a pleasant, peppermint-like odor. It has a viscous consistency and is often seen in essential oils.

Comment on solubility

Solubility of (1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanol

The solubility of the compound (1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanol can be intriguing to analyze, particularly given its structural features. This compound showcases the ability to interact with solvents in specific ways owing to its functional groups.

  • Hydrophilicity: The presence of the hydroxyl group (-OH) significantly enhances its affinity for polar solvents like water. This is due to the ability of the hydroxyl group to engage in hydrogen bonding.
  • Hydrophobic Characteristics: The cyclohexanol structure contributes to a hydrophobic portion, which can lead to lower solubility in non-polar solvents.
  • Miscibility: As a result of its dual nature, the compound may exhibit partial miscibility across different solvent systems, particularly in solvents like ethanol or methanol but potentially limited in more hydrophobic solvents.

In summary, the solubility of this compound can be described as moderate to good in polar solvents due to the hydroxyl group’s influence, while being relatively poor in non-polar environments. Understanding such solubility characteristics is crucial for applications in pharmaceuticals, environmental science, and materials chemistry.

Interesting facts

Interesting Facts about (1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanol

This intriguing compound, classified as a tertiary alcohol, showcases a unique arrangement of atoms that brings about various intriguing properties and potential applications.

Chemical Characteristics

  • Stereochemistry: The specific stereochemistry of this compound is notable, as its (1R,2R,5R) configuration can influence its reactivity and interaction with biological systems. Such chirality often plays a crucial role in pharmacology and biochemical activities.
  • Functional Groups: The presence of the hydroxyl (-OH) group makes this compound an alcohol, which often contributes to properties such as hydrogen bonding and solubility in polar solvents.
  • Cyclohexanol Derivative: Being a derivative of cyclohexanol, this compound can be explored for its potential in creating various cyclic compounds that may have significant applications in pharmaceutical chemistry.

Applications and Importance

Due to its structure and functional groups, this compound could potentially serve in various fields, including:

  • Pharmaceuticals: Tertiary alcohols like this one can act as intermediates in drug synthesis, presenting opportunities for developing new therapeutic agents.
  • Aromas and Fragrances: The unique structure may lend itself to applications in fragrance chemistry, contributing to the development of novel scents.
  • Surfactants: This compound could also find utility in the formulation of surfactants utilized in cleaning and emulsifying processes.

Conclusion

The chemical complexity of (1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanol opens up a myriad of exploration opportunities. As we delve deeper into the study of such compounds, the potential for innovation and discovery goes hand in hand with the fundamental principles of organic chemistry.

Synonyms
Menthoglycol
3564-98-5
trans-p-Menthane-3,8-diol
(1R,2R,5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
Isopulegol hydrate
(-)-3,8-p-Menthanediol
PMD38
91739-72-9
(1R,3R,4R)-p-menthane-3,8-diol
p-MENTHANE-3,8-DIOL, cis-1,3,trans-1,4-
AAL436QJ5W
1beta,3beta,4alpha-p-menthane-3,8-diol
EB999AF32A
(+/-)-trans-p-Menthane-3,8-diol
(1R,2R,5R)-2-(1-hydroxy-1-methylethyl)-5-methylcyclohexanol
(1R,3R,4R)-2-hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol
Cyclohexanemethanol, 2-hydroxy-.alpha.,.alpha.,4-trimethyl-, (1R,2R,4R)-
8-hydroxymenthol
( inverted exclamation markA)-p-Menthane-3,8-trans-diol
rel-(1R,2R,4R)-2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol
(+-)-Isopulegol hydrate
UNII-AAL436QJ5W
EPA Pesticide Chemical Code 011550
UNII-EB999AF32A
rel-(1R,2R,4R)-2-Hydroxy-?,?,4-trimethylcyclohexanemethanol; (+/-)-Isopulegol Hydrate
Menthoglycol [WHO-DD]
trans-2-(2-Hydroxypropan-2-yl)-5-methylcyclohexanol
1,4-menthane-3,8-diol
Cyclohexanemethanol, 2-hydroxy-alpha,alpha,4-trimethyl-, (1-alpha,2-beta,4-beta)-
SCHEMBL80732
(1R,2R,5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexanol
GTPL2472
Cyclohexanemethanol, 2-hydroxy-.alpha.,.alpha.,4-trimethyl-, (1R,2R,4E)-
DTXSID5035084
CHEBI:16053
MENTHOGLYCOL, (+/-)-
DTXSID801033610
(+/-)-ISOPULEGOL HYDRATE
Cyclohexanemethanol, 2-hydroxy-.alpha.,.alpha.,4-trimethyl-, (1-.alpha.,2-.beta.,4-.beta.)-
Cyclohexanemethanol, 2-hydroxy-alpha,alpha,4-trimethyl-, (1R,2R,4R)-
AKOS037646772
Cyclohexanemethanol, 2-hydroxy-alpha,alpha,4-trimethyl-, (1R,2R,4E)-rel-
3,8-P-MENTHANEDIOL, (-)-
HY-W436777
LMPR0102090063
AS-70737
1beta,3beta,4alpha--p-menthane-3,8-diol
1beta,3beta,4alpha-para-menthane-3,8-diol
CS-0543232
NS00115909
p-Menthane-3,8-diol (cis-1,3,trans-1,4)
C02904
Q27088421
2-(1-hydroxy-1-methyl-ethyl)-5-methyl-cyclohexan-1-ol
(1R,2R,4R)-2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol
rel-(1R,2R,4R)-2-Hydroxy-|A,|A,4-trimethylcyclohexanemethanol
cyclohexanemethanol, 2-hydroxy-alpha,alpha,4-trimethyl-, (1R,2R, 4E)-rel
CYCLOHEXANEMETHANOL, 2-HYDROXY-.ALPHA.,.ALPHA.,4-TRIMETHYL-, (1R,2R,4R)-REL-
cyclohexanemethanol, 2-hydroxy-alpha,alpha,4-trimethyl-, (1- alpha,2-beta,4-beta)
CYCLOHEXANEMETHANOL, 2-HYDROXY-.ALPHA.,.ALPHA.,4-TRIMETHYL-, (1.ALPHA.,2.BETA.,4.BETA.)-
CYCLOHEXANEMETHANOL, 2-HYDROXY-.ALPHA.,.ALPHA.,4-TRIMETHYL-, (1R-(1.ALPHA.,2.BETA.,4.BETA.))-