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Menthol

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Identification
Molecular formula
C10H20O
CAS number
1490-04-6
IUPAC name
(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol
State
State

At room temperature, menthol is a solid. It is stable under normal conditions and exhibits a characteristic cooling sensation when applied or consumed. The compound is a popular ingredient in various products due to its aromatic and sensory properties.

Melting point (Celsius)
38.00
Melting point (Kelvin)
311.15
Boiling point (Celsius)
212.00
Boiling point (Kelvin)
485.15
General information
Molecular weight
156.27g/mol
Molar mass
156.2680g/mol
Density
0.8900g/cm3
Appearence

Menthol appears as colorless or white crystals. It is often found in a waxy, crystalline form. The compound has a strong minty odor, which is characteristic and makes it easily recognizable. The crystalline form can appear needle-like or in flake form.

Comment on solubility

Solubility of (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol

(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol is an interesting compound when it comes to solubility. Its unique molecular structure can influence its interactions with solvents and the environment. Here are some key points regarding its solubility:

  • Polarity: The presence of hydroxyl (-OH) groups in the molecular structure enhances the polarity of this compound, which typically increases solubility in polar solvents such as water.
  • Hydrophobic Characteristics: The alkyl groups (isopropyl and methyl) provide hydrophobic characteristics, which can lead to limited solubility in polar solvents while increasing solubility in non-polar solvents like hexane or benzene.
  • Temperature Influence: Solubility can also vary with temperature. Typically, an increase in temperature will enhance the solubility of organic compounds in organic solvents.
  • pH Sensitivity: Being a chiral alcohol, its solubility may also be influenced by the pH of the solution, especially in biological systems.

In conclusion, while (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol demonstrates notable solubility characteristics, the exact solubility can be dependent on the solvent environment, temperature, and other physicochemical factors. Therefore, it is crucial to consider these elements when evaluating its solubility for practical applications.

Interesting facts

Exploring (1R,2S,5R)-2-Isopropyl-5-Methyl-Cyclohexanol

(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol is a fascinating compound renowned for its unique structural configuration and its applications in the fragrance industry. Below are some compelling points that highlight its significance:

  • Stereochemistry: This compound showcases an interesting array of stereoisomers due to its multiple chiral centers. Understanding these configurations provides insights into how molecular shapes influence properties and reactivity.
  • Fragrance Component: It is often used as a component in perfumes and scents, contributing to the overall olfactory profile. Chemists study this compound to safely create fragrances that resonate with consumers.
  • Biological Relevance: Compounds similar to (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol are frequently studied for their potential biological activities, including antimicrobial properties.
  • Synergistic Effects: When blended with other fragrance compounds, it may enhance or stabilize various scent notes, making it an essential player in the formulation of complex fragrances.

Applications and Research

Researching (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol extends beyond the confines of perfumery. It plays a role in:

  • Chemical Synthesis: Its unique structure makes it a valuable intermediate for synthesizing other complex organic molecules.
  • Flavoring Agents: Similar derivatives are investigated for use as food flavorings, adding delicious and aromatic notes to various products.

In conclusion, (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol is not only a compound of keen interest due to its structural features but also plays a vital role in both chemistry and industry. As researchers continue to uncover its properties and potential, there is no doubt that this compound will remain a topic of discussion in the fields of organic chemistry and material science.

Synonyms
l-Menthol
(-)-menthol
2216-51-5
Levomenthol
l-(-)-Menthol
Menthomenthol
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
Menthacamphor
Peppermint camphor
(1r,2s,5r)-(-)-menthol
U.S.P. Menthol
Levomentholum
Racementhol
Hexahydrothymol
(-)-Menthyl alcohol
Menthol racemic
(1R)-(-)-Menthol
d,l-Menthol
(-)-(1R,3R,4S)-Menthol
89-78-1
(R)-(-)-Menthol
D-(-)-Menthol
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-
p-Menthan-3-ol
(-)-trans-p-Menthan-cis-ol
rac-Menthol
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
1-Menthol
(L)-MENTHOL
Menthol(-)
levomentol
Menthol natural
Menthol, (1R,3R,4S)-(-)-
(1R,3R,4S)-(-)-MENTHOL
Menthol, dl-
NCI-C50000
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel-
1R-Menthol
NSC 62788
Racementol
Racemic menthol
Water-soluble menthol
(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
(1R,2S,5R)-Menthol
MFCD00062979
(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol
BZ1R15MTK7
(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanol
(+/-)-Menthol
(1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol
CHEMBL470670
YS08XHA860
DTXSID1020805
DTXSID1022180
CHEBI:15409
NSC2603
Headache crystals
NSC-2603
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol
rel-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
FEMA No. 2665
NSC-62788
Menthol (VAN)
Racementholum
Thymomenthol
Menthol, cis-1,3,trans-1,4-
l-Menthol (natural)
NSC 2603
(+-)-Menthol
I-menthol
Menthol racemique
Levomenthol; (-)-Menthol
Levomenthol [INN:BAN]
Racementhol [INN:BAN]
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1R-(1.alpha.,2.beta.,5.alpha.)]-
Menthol natural, brazilian
Menthol, l-
Racementol [INN-Spanish]
Levomentholum [INN-Latin]
Menthol racemique [French]
Racementholum [INN-Latin]
DTXCID802180
Tra-kill tracheal mite killer
(1alpha,2beta,5alpha)-5-methyl-2(1-methylethyl)cyclohexanol
DTXCID101305276
MEGGEZONE
CAS-89-78-1
CCRIS 375
CAS-2216-51-5
l-Menthol (TN)
CCRIS 3728
CCRIS 4666
HSDB 5662
SR-05000001936
(-)-p-Menthan-3-ol
EINECS 201-939-0
EINECS 218-690-9
EINECS 239-388-3
UNII-BZ1R15MTK7
(1R,2S,5R)-rel-2-Isopropyl-5-methylcyclohexanol
BRN 1902288
BRN 3194263
UNII-YS08XHA860
(+-)-(1R*,3R*,4S*)-Menthol
AI3-52408
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.beta.,5.alpha.)-
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R-(1alpha,2beta,5alpha))-
CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, (1R-(1.ALPHA.,2.BETA.,5.ALPHA.))-
L-Menthol natural
1 -menthol
NCGC00159382-02
98167-53-4
L-MENTHOLUM
l-Menthol (JP18)
Spectrum_000305
DL-Menthol (Standard)
LEVOMENTHOL [II]
MENTHOL [MI]
5-Methyl-2-(1-methylethyl)cyclohexanol, (1alpha,2beta,5alpha)-
L-MENTHOL [JAN]
Menthol, (+/-)-
Spectrum2_000855
Spectrum3_001561
Spectrum5_001060
LEVOMENTHOL [INN]
RACEMENTHOL [INN]
M0545
DL-MENTHOL [JAN]
Menthol,3,trans-1,4-
(-)-Menthol (Standard)
LEVOMENTHOL [HSDB]
RACEMENTHOL [HSDB]
pound - pound(c)-Menthol
EC 201-939-0
EC 218-690-9
SCHEMBL4613
BSPBio_003062
KBioSS_000785
LEVOMENTHOL [WHO-DD]
2-06-00-00052 (Beilstein Handbook Reference)
4-06-00-00151 (Beilstein Handbook Reference)
MLS002207256
DivK1c_000820
MENTHOL RACEMATE [MI]
SPECTRUM1503134
Menthol,3R,4S)-(-)-
SPBio_000869
GTPL2430
NPO-11
(-)-Menthol, USP, 97%
HMS502I22
HY-Y1683R
KBio1_000820
KBio2_000785
KBio2_003353
KBio2_005921
KBio3_002562
NOOLISFMXDJSKH-KXUCPTDWSA-
MSK1669
(-)-Menthol, analytical standard
NINDS_000820
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,3R,4S)-
HMS1922G13
HMS2092L14
HMS3885J18
LEVOMENTHOL [EP MONOGRAPH]
Pharmakon1600-01503134
NSC62788
L-Menthol, >=99%, FCC, FG
Tox21_111620
Tox21_201823
Tox21_201919
Tox21_202608
Tox21_302999
Tox21_303028
WLN: L6TJ AY1&1 BQ D1
BDBM50318482
CCG-40300
Cyclohexanol, 2-isopropyl-5-methyl-
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1alpha,2beta,5alpha)-
HY-75161R
NSC758395
s4714
AKOS016842647
(1R, 2S, 5R-)-(-)-Menthol
1ST1669
BS-3863
DB00825
FM44476
FR15930
LMPR0102090001
NSC-758395
SDCCGMLS-0066659.P001
(-)-TRANS-P-METHAN-CIS-3-OL
IDI1_000820
WLN: L6TJ AY1&1 DQ D1 -L
NCGC00164247-01
NCGC00164247-02
NCGC00164247-03
NCGC00256525-01
NCGC00256561-01
NCGC00259372-01
NCGC00259468-01
NCGC00260156-01
FEMA NO. 2665, (-)-
SMR001306785
L-Menthol, natural, >=99%, FCC, FG
SBI-0051777.P002
NS00068027
NS00102112
S5868
EN300-92163
FEMA NO. 2665, (+/-)-
Menthol (racemic) 100 microg/mL in Methanol
(+/-)-(1R*,3R*,4S*)-MENTHOL
(1R,2S,5R)-(-)-Menthol, synthetic pellets
C00400
Cyclohexanol, (1.alpha.,2.beta.,5.alpha.)-
D00064
D70313
(-)-Menthol;Natural menthol crystal;Levomenthol
AB00052320_02
L-Menthol|Levomenthol|Menthomenthol|Menthacamphor
(1R,2S,5R)-(-)-Menthol, >=99%, sublimed
Q407418
SR-05000001936-1
SR-05000001936-2
(-)-Menthol, primary pharmaceutical reference standard
(1R,2S,5R)-(-)-Menthol, ReagentPlus(R), 99%
2-Isopropyl-5-methylcyclohexanol-, (1R,2S,5R)- #
BRD-K50329370-001-08-2
BRD-K50329370-001-09-0
Cyclohexanol, [1R-(1.alpha.,2.beta.,5.alpha.)]-
(1R,2S,5R)-5-methyl-2-propan-2-yl-cyclohexan-1-ol
Z1255438640
(1R,2S,5R)-(-)-Menthol, Vetec(TM) reagent grade, 98%
6C6A4A8C-A054-468C-A1F0-F29E39838CF2
(1R, 2S, 5R)-5-methyl-2-(1-methylethyl)cyclohexyl alcohol
Menthol, United States Pharmacopeia (USP) Reference Standard
(1R,2S,5R)-REL-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANOL
L-Menthol, Pharmaceutical Secondary Standard; Certified Reference Material
(-)-Menthol, puriss., meets analytical specification of Ph. Eur., BP, USP, 98.0-102.0%
(1R,2S,5R)-rel-5-Methyl-2-(1-methylethyl)cyclohexanol;Hexahydrothymol;Menthacamphor;Menthol
(1R-(1-.alpha.,2-.beta.,5-.alpha.))-5-Methyl-2-(1-methylethyl)cyclohexanol
114376-98-6
InChI=1/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
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