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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-12 19:15:31 UTC

Update Date

2023-02-21 17:16:37 UTC

HMDB ID

HMDB0003352

Secondary Accession Numbers

HMDB03352

Metabolite Identification

Common Name

Menthol

Description

Menthol is an alcohol produced from mint oils or prepared synthetically. Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0003352
     RDKit          3D
Menthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.4893   -0.2512    1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    0.3752   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -0.3313   -1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    0.2796   -0.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1323   -1.1308   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531   -1.1647   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0986   -0.2923    0.4170 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5508   -0.2350   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499    1.1312    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777    1.0109    0.7827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4860    2.2780    0.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704   -1.3264    1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071   -0.1681    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    0.2289    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920    1.4485   -0.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500    0.1708   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -0.1682   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.3942   -1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    0.7824   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -1.6998    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -1.6311   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6886   -2.2178   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -0.9447   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.6910    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822   -1.1275    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.2675   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0058    0.7136    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    1.6748    1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719    1.5713   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    0.4332    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185    2.9429    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END

HMDB0003352
     RDKit          3D
Menthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.4893   -0.2512    1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    0.3752   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -0.3313   -1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    0.2796   -0.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1323   -1.1308   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531   -1.1647   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0986   -0.2923    0.4170 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5508   -0.2350   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499    1.1312    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777    1.0109    0.7827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4860    2.2780    0.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704   -1.3264    1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071   -0.1681    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    0.2289    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920    1.4485   -0.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500    0.1708   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -0.1682   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.3942   -1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    0.7824   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -1.6998    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -1.6311   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6886   -2.2178   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -0.9447   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.6910    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822   -1.1275    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.2675   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0058    0.7136    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    1.6748    1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719    1.5713   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    0.4332    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185    2.9429    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END

COMPND    HMDB0003352
HETATM    1  C1  UNL     1      -2.489  -0.251   1.220  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.104   0.375  -0.101  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.857  -0.331  -1.198  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.627   0.280  -0.340  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.132  -1.131  -0.374  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.353  -1.165  -0.553  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.099  -0.292   0.417  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.551  -0.235  -0.002  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.550   1.131   0.416  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.078   1.011   0.783  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.486   2.278   0.942  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.270  -1.326   1.207  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.607  -0.168   1.313  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.008   0.229   2.079  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.392   1.448  -0.112  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.650   0.171  -2.184  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.946  -0.168  -0.989  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.614  -1.394  -1.265  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.360   0.782  -1.276  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.379  -1.700   0.539  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.588  -1.631  -1.255  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.689  -2.218  -0.355  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.683  -0.945  -1.590  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.048  -0.691   1.452  1.00  0.00           H  
HETATM   25  H14 UNL     1       4.082  -1.128   0.411  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.599  -0.268  -1.105  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.006   0.714   0.338  1.00  0.00           H  
HETATM   28  H17 UNL     1       2.092   1.675   1.217  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.672   1.571  -0.574  1.00  0.00           H  
HETATM   30  H19 UNL     1      -0.009   0.433   1.723  1.00  0.00           H  
HETATM   31  H20 UNL     1       0.019   2.943   0.402  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   10   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   24
CONECT    8   25   26   27
CONECT    9   10   28   29
CONECT   10   11   30
CONECT   11   31
END

HMDB0003352
     RDKit          3D
Menthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.4893   -0.2512    1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    0.3752   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -0.3313   -1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    0.2796   -0.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1323   -1.1308   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531   -1.1647   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0986   -0.2923    0.4170 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5508   -0.2350   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499    1.1312    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777    1.0109    0.7827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4860    2.2780    0.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704   -1.3264    1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071   -0.1681    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    0.2289    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920    1.4485   -0.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500    0.1708   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -0.1682   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.3942   -1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    0.7824   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -1.6998    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -1.6311   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6886   -2.2178   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -0.9447   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.6910    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822   -1.1275    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.2675   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0058    0.7136    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    1.6748    1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719    1.5713   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    0.4332    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185    2.9429    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-(1R,3R,4S)-Menthol	ChEBI
(1alpha,2beta,5alpha)-5-Methyl-2(1-methylethyl)cyclohexanol	ChEBI
(1R,3R,4S)-(-)-Menthol	ChEBI
(1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol	ChEBI
L-Menthol	ChEBI
Levomenthol	ChEBI
Levomentholum	ChEBI
Levomentol	ChEBI
(1a,2b,5a)-5-Methyl-2(1-methylethyl)cyclohexanol	Generator
(1Α,2β,5α)-5-methyl-2(1-methylethyl)cyclohexanol	Generator
(1R-(1-a,2-b,5-a))-5-Methyl-2-(1-methylethyl)cyclohexanol	Generator
(1R-(1-Α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanol	Generator
(-)-Menthyl alcohol	HMDB
(-)-trans-p-Menthan-cis-ol	HMDB
(1R)-(-)-Menthol	HMDB
(1R,2S,5R)-(-)-Menthol	HMDB
(R)-(-)-Menthol	HMDB
1-Menthol	HMDB
2-Isopropyl-5-methylcyclohexanol	HMDB
5-Methyl-2-(1-methylethyl)cyclohexanol	HMDB
5-Methyl-2-propan-2-ylcyclohexan-1-ol	HMDB
D-(-)-Menthol	HMDB
Hexahydrothymol	HMDB
L-(-)-Menthol	HMDB
Menthacamphor	HMDB
Menthomenthol	HMDB
p-Menthan-3-ol	HMDB
Peppermint camphor	HMDB
U.S.p. menthol	HMDB
Kerasal	HMDB
Menthol, (1alpha,2beta,5alpha)-isomer	HMDB
Menthol	MeSH

Chemical Formula

C₁₀H₂₀O

Average Molecular Weight

156.269

Monoisotopic Molecular Weight

156.151415264

IUPAC Name

(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

Traditional Name

menthol

CAS Registry Number

2216-51-5

SMILES

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

InChI Identifier

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1

InChI Key

NOOLISFMXDJSKH-KXUCPTDWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexanol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

p-menthan-3-ol (CHEBI:15409 )
Menthane monoterpenoids (C00400 )
Cyclic monoterpenes (C00400 )
Menthane monoterpenoids (LMPR0102090001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0003352)
Extracellular (HMDB: HMDB0003352)

Cell

Nerve cell (HMDB: HMDB0003352)
Neuron (HMDB: HMDB0003352)

Stratum Corneum (HMDB: HMDB0003352)

Organ

Bladder (HMDB: HMDB0003352)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0003352)

Organ substructure

Mouth (HMDB: HMDB0003352)

Source

Exogenous

Exogenous (HMDB: HMDB0003352)

Food

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	43 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.49 mg/mL at 25 °C	Not Available
LogP	3.40	GRIFFIN,S ET AL. (1999)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.56 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.66	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.45 m³·mol⁻¹	ChemAxon
Polarizability	19.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.808	31661259
DarkChem	[M-H]-	135.56	31661259
DeepCCS	[M+H]+	143.205	30932474
DeepCCS	[M-H]-	140.847	30932474
DeepCCS	[M-2H]-	175.177	30932474
DeepCCS	[M+Na]+	150.213	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.4	32859911
AllCCS	[M+NH4]+	139.8	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	141.3	32859911
AllCCS	[M+Na-2H]-	143.0	32859911
AllCCS	[M+HCOO]-	145.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Menthol	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O	1626.6	Standard polar	33892256
Menthol	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O	1167.3	Standard non polar	33892256
Menthol	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O	1195.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Menthol,1TMS,isomer #1	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[Si](C)(C)C	1244.5	Semi standard non polar	33892256
Menthol,1TBDMS,isomer #1	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[Si](C)(C)C(C)(C)C	1470.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Menthol GC-MS (1 TMS)	splash10-0006-1900000000-cc06fe70d7649d059f92	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Menthol EI-B (Non-derivatized)	splash10-00ea-9100000000-0be605183591bf5f33a0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Menthol EI-B (Non-derivatized)	splash10-00ea-9100000000-977cf0c036d597693beb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Menthol GC-MS (Non-derivatized)	splash10-0006-1900000000-cc06fe70d7649d059f92	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Menthol GC-EI-Q (Non-derivatized)	splash10-00ym-9100000000-ff2f7ebe48769147a112	2020-07-08	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9600000000-fcf4b2a96455b111f889	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthol GC-MS (1 TMS) - 70eV, Positive	splash10-01w0-9520000000-26cc8cab97979ec9fb4d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00ea-9100000000-602436010653202a4da9	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Menthol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-053r-9300000000-d9c35833e73c8655fb23	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Menthol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0ldl-9000000000-abf2f837df49fbedc53c	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Menthol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0007-9000000000-adee6385265c6606326d	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Menthol EI-B (JEOL JMS-D-3000) , Positive-QTOF	splash10-00ea-9100000000-e3f1b7b69a021063fabb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Menthol EI-B (JEOL JMS-DX-300) , Positive-QTOF	splash10-00ea-9100000000-d69777874c9615b7e751	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 10V, Positive-QTOF	splash10-052r-0900000000-39d327015211bdc2b4e8	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 20V, Positive-QTOF	splash10-052r-6900000000-67e6c41c2a8d759d6caf	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 40V, Positive-QTOF	splash10-0aor-9200000000-88888989ba15a9dc0269	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 10V, Negative-QTOF	splash10-0a4i-0900000000-3a700dc611fb070e6b45	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 20V, Negative-QTOF	splash10-0a4i-0900000000-86ed17c709dc4636ad41	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 40V, Negative-QTOF	splash10-0bti-6900000000-fc116bf41f068d3f6f75	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 10V, Positive-QTOF	splash10-05mk-9800000000-bb8a9e58bdc61e2654e6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 20V, Positive-QTOF	splash10-053e-9100000000-6405f7fe35f6f6bdc8c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 40V, Positive-QTOF	splash10-0006-9000000000-fee5c7d55bf523973cbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 10V, Negative-QTOF	splash10-0a4i-0900000000-f6034c6a8245c68a37ac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 20V, Negative-QTOF	splash10-0a4i-0900000000-7efa42d43b7858e2c2ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthol 40V, Negative-QTOF	splash10-0zfr-0900000000-b6eef0a7f66ac7e97e78	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Bladder
Epidermis
Neuron
Skeletal Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.064 (0.033 - 0.159) uM	Adult (>18 years old)	Both	Normal	15342616	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24922509	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24657864	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zhang, S., Liu, L...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) non progressor	24922509	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) progressor	24922509	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Nonalcoholic fatty liver disease	23454028	details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Celiac disease	24657864	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Pervasive developmental disorder not otherwise specified
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Celiac disease
Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

DB00825

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Menthol

METLIN ID

Not Available

PubChem Compound

16666

PDB ID

Not Available

ChEBI ID

15409

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bergner, Eike Johannes; Ebel, Klaus; Johann, Thorsten; Loeber, Oliver. Method for the production of menthol. PCT Int. Appl. (2006), 32 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. [PubMed:12654248 ]
Stein RJ, Santos S, Nagatomi J, Hayashi Y, Minnery BS, Xavier M, Patel AS, Nelson JB, Futrell WJ, Yoshimura N, Chancellor MB, De Miguel F: Cool (TRPM8) and hot (TRPV1) receptors in the bladder and male genital tract. J Urol. 2004 Sep;172(3):1175-8. [PubMed:15311065 ]
Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. [PubMed:7529306 ]
Haeseler G, Maue D, Grosskreutz J, Bufler J, Nentwig B, Piepenbrock S, Dengler R, Leuwer M: Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol. Eur J Anaesthesiol. 2002 Aug;19(8):571-9. [PubMed:12200946 ]
Stich HF, Stich W: Chromosome-damaging activity of saliva of betel nut and tobacco chewers. Cancer Lett. 1982 Mar-Apr;15(3):193-202. [PubMed:7116324 ]
Haahr AM, Bardow A, Thomsen CE, Jensen SB, Nauntofte B, Bakke M, Adler-Nissen J, Bredie WL: Release of peppermint flavour compounds from chewing gum: effect of oral functions. Physiol Behav. 2004 Sep 15;82(2-3):531-40. [PubMed:15276819 ]
Mukerji G, Yiangou Y, Corcoran SL, Selmer IS, Smith GD, Benham CD, Bountra C, Agarwal SK, Anand P: Cool and menthol receptor TRPM8 in human urinary bladder disorders and clinical correlations. BMC Urol. 2006 Mar 6;6:6. [PubMed:16519806 ]
Rohacs T, Lopes CM, Michailidis I, Logothetis DE: PI(4,5)P2 regulates the activation and desensitization of TRPM8 channels through the TRP domain. Nat Neurosci. 2005 May;8(5):626-34. Epub 2005 Apr 24. [PubMed:15852009 ]
Valdez JS, Martin DK, Mayersohn M: Sensitive and selective gas chromatographic methods for the quantitation of camphor, menthol and methyl salicylate from human plasma. J Chromatogr B Biomed Sci Appl. 1999 Jun 11;729(1-2):163-71. [PubMed:10410939 ]
Gelal A, Jacob P 3rd, Yu L, Benowitz NL: Disposition kinetics and effects of menthol. Clin Pharmacol Ther. 1999 Aug;66(2):128-35. [PubMed:10460066 ]
Grigoleit HG, Grigoleit P: Pharmacology and preclinical pharmacokinetics of peppermint oil. Phytomedicine. 2005 Aug;12(8):612-6. [PubMed:16121523 ]
Xu H, Blair NT, Clapham DE: Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci. 2005 Sep 28;25(39):8924-37. [PubMed:16192383 ]
Narishetty ST, Panchagnula R: Effect of L-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine. J Control Release. 2005 Jan 20;102(1):59-70. [PubMed:15653134 ]
Prescott J: The generalizability of capsaicin sensitization and desensitization. Physiol Behav. 1999 Jul;66(5):741-9. [PubMed:10405101 ]
Liu Y, Ye X, Feng X, Zhou G, Rong Z, Fang C, Chen H: Menthol facilitates the skin analgesic effect of tetracaine gel. Int J Pharm. 2005 Nov 23;305(1-2):31-6. Epub 2005 Oct 10. [PubMed:16219435 ]

Enzymes

Enzyme Details

1. Transient receptor potential cation channel subfamily M member 8

General function:: Involved in ion channel activity
Specific function:: Receptor-activated non-selective cation channel involved in detection of sensations such as coolness, by being activated by cold temperature below 25 degrees Celsius. Activated by icilin, eucalyptol, menthol, cold and modulation of intracellular pH. Involved in menthol sensation. Permeable for monovalent cations sodium, potassium, and cesium and divalent cation calcium. Temperature sensing is tightly linked to voltage-dependent gating. Activated upon depolarization, changes in temperature resulting in graded shifts of its voltage-dependent activation curves. The chemical agonists menthol functions as a gating modifier, shifting activation curves towards physiological membrane potentials. Temperature sensitivity arises from a tenfold difference in the activation energies associated with voltage-dependent opening and closing
Gene Name:: TRPM8
Uniprot ID:: Q7Z2W7
Molecular weight:: 127684.0

References

Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. [PubMed:12654248 ]
Behrendt HJ, Germann T, Gillen C, Hatt H, Jostock R: Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. Br J Pharmacol. 2004 Feb;141(4):737-45. Epub 2004 Feb 2. [PubMed:14757700 ]
Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, Earley TJ, Patapoutian A: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57. [PubMed:15046718 ]
Andersson DA, Chase HW, Bevan S: TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH. J Neurosci. 2004 Jun 9;24(23):5364-9. [PubMed:15190109 ]
Stein RJ, Santos S, Nagatomi J, Hayashi Y, Minnery BS, Xavier M, Patel AS, Nelson JB, Futrell WJ, Yoshimura N, Chancellor MB, De Miguel F: Cool (TRPM8) and hot (TRPV1) receptors in the bladder and male genital tract. J Urol. 2004 Sep;172(3):1175-8. [PubMed:15311065 ]
Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. [PubMed:7529306 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Kappa-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:: OPRK1
Uniprot ID:: P41145
Molecular weight:: 42644.7

References

Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A, Ghelardini C: Menthol: a natural analgesic compound. Neurosci Lett. 2002 Apr 12;322(3):145-8. [PubMed:11897159 ]
Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. [PubMed:7851817 ]

Enzyme Details

3. Transient receptor potential cation channel subfamily V member 3

General function:: Involved in calcium channel activity
Specific function:: Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 degrees Celsius. Activation exhibits an outward rectification. May associate with TRPV1 and may modulate its activity
Gene Name:: TRPV3
Uniprot ID:: Q8NET8
Molecular weight:: 90635.1

References

Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM: More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43. Epub 2006 Jul 7. [PubMed:16829128 ]

Enzyme Details

4. Transient receptor potential cation channel subfamily A member 1

General function:: Not Available
Specific function:: Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function. Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes. Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)- tetrahydrocannabinol (THC), the psychoactive component of marijuana. Not involved in menthol sensation. May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system
Gene Name:: TRPA1
Uniprot ID:: O75762
Molecular weight:: 127485.8

References

Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. [PubMed:12654248 ]
Namer B, Seifert F, Handwerker HO, Maihofner C: TRPA1 and TRPM8 activation in humans: effects of cinnamaldehyde and menthol. Neuroreport. 2005 Jun 21;16(9):955-9. [PubMed:15931068 ]
Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM: More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43. Epub 2006 Jul 7. [PubMed:16829128 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Menthol (HMDB0003352)

MOL for HMDB0003352 (Menthol)

3D MOL for HMDB0003352 (Menthol)

3D SDF for HMDB0003352 (Menthol)

3D-SDF for HMDB0003352 (Menthol)

PDB for HMDB0003352 (Menthol)

3D PDB for HMDB0003352 (Menthol)

SMILES for HMDB0003352 (Menthol)

INCHI for HMDB0003352 (Menthol)

Structure for HMDB0003352 (Menthol)

3D Structure for HMDB0003352 (Menthol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

References

References