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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:08 UTC

Update Date

2022-03-07 02:52:12 UTC

HMDB ID

HMDB0029557

Secondary Accession Numbers

HMDB29557

Metabolite Identification

Common Name

Dihydroisophorol

Description

Dihydroisophorol, also known as homomenthol, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Dihydroisophorol is a cool, mentholic, and mint tasting compound. Based on a literature review very few articles have been published on Dihydroisophorol.

Structure

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

COMPND    HMDB0029557
HETATM    1  C1  UNL     1       2.308  -1.111   0.110  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.423  -0.216  -0.763  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.480   1.156  -0.191  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.453   1.435   0.861  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.457   2.811   1.102  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.917   0.998   0.515  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.032  -0.344  -0.124  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.319  -1.358   0.968  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.301  -0.299  -0.983  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.083  -0.796  -0.963  1.00  0.00           C  
HETATM   11  H1  UNL     1       2.759  -1.937  -0.501  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.113  -0.515   0.588  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.649  -1.575   0.857  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.995  -0.154  -1.739  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.486   1.310   0.301  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.416   1.961  -0.951  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.794   0.960   1.815  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.110   3.226   0.405  1.00  0.00           H  
HETATM   19  H9  UNL     1      -1.517   1.005   1.469  1.00  0.00           H  
HETATM   20  H10 UNL     1      -1.392   1.783  -0.113  1.00  0.00           H  
HETATM   21  H11 UNL     1      -2.342  -1.723   0.973  1.00  0.00           H  
HETATM   22  H12 UNL     1      -0.652  -2.257   0.856  1.00  0.00           H  
HETATM   23  H13 UNL     1      -1.132  -0.915   1.985  1.00  0.00           H  
HETATM   24  H14 UNL     1      -2.448  -1.309  -1.384  1.00  0.00           H  
HETATM   25  H15 UNL     1      -3.151   0.071  -0.386  1.00  0.00           H  
HETATM   26  H16 UNL     1      -2.117   0.412  -1.803  1.00  0.00           H  
HETATM   27  H17 UNL     1       0.186  -1.917  -0.842  1.00  0.00           H  
HETATM   28  H18 UNL     1      -0.173  -0.702  -2.062  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   10   14
CONECT    3    4   15   16
CONECT    4    5    6   17
CONECT    5   18
CONECT    6    7   19   20
CONECT    7    8    9   10
CONECT    8   21   22   23
CONECT    9   24   25   26
CONECT   10   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3,5-Trimethyl-1-cyclohexanol	ChEBI
Homomenthol	ChEBI
1-Methyl-3-dimethylcyclohexanol-5	HMDB
3,3,5-Trimethyl-(1R,5S)-rel-cyclohexanol	HMDB
3,3,5-Trimethyl-cis-cyclohexanol	HMDB
3,3,5-Trimethyl-cyclohexanol	HMDB
3,3,5-Trimethyl-trans-cyclohexanol	HMDB
3,3,5-Trimethylcyclohexanol (c,t)	HMDB
3,3,5-Trimethylcyclohexanol,camp t	HMDB
3,5,5-Trimethylcyclohexanol	HMDB
cis-3,3,5-Trimethylcyclohexanol	HMDB
Cyclonol	HMDB
dihydro-Isophorol	HMDB
FEMA 3962	HMDB
TMC	HMDB
trans-3,3,5-Trimethylcyclohexanol	HMDB
trans-3,5,5-Trimethylcyclohexan-1-ol	HMDB
Trimethylcyclohexanol	HMDB
Dihydroisophorol	ChEBI
3,3,5-Trimethylcyclohexanol, (cis)-isomer	MeSH
3,3,5-Trimethylcyclohexanol, (trans)-isomer	MeSH

Chemical Formula

C₉H₁₈O

Average Molecular Weight

142.2386

Monoisotopic Molecular Weight

142.135765198

IUPAC Name

3,3,5-trimethylcyclohexan-1-ol

Traditional Name

3,3,5-trimethylcyclohexanol

CAS Registry Number

116-02-9

SMILES

CC1CC(O)CC(C)(C)C1

InChI Identifier

InChI=1S/C9H18O/c1-7-4-8(10)6-9(2,3)5-7/h7-8,10H,4-6H2,1-3H3

InChI Key

BRRVXFOKWJKTGG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

Alternative Parents

Substituents

Cyclohexanol
Cyclic alcohol
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:59065 )
cyclohexanols (CHEBI:59065 )

Ontology

Cell membrane (HMDB: HMDB0029557)

Cellular substructure

Membrane (HMDB: HMDB0029557)

Source

Endogenous

Endogenous (HMDB: HMDB0029557)

Exogenous

Food

Food (HMDB: HMDB0029557)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0029557)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	30.00 to 34.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	80.00 °C. @ 20.00 mm Hg	The Good Scents Company Information System
Water Solubility	840.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.734 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.33 g/L	ALOGPS
logP	2.86	ALOGPS
logP	2.15	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	18.96	ChemAxon
pKa (Strongest Basic)	-1.1	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	0	ChemAxon
Refractivity	42.85 m³·mol⁻¹	ChemAxon
Polarizability	17.64 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]+	131.567	31661259
DarkChem	[M-H]-	128.421	31661259
DeepCCS	[M+H]+	141.073	30932474
DeepCCS	[M-H]-	138.422	30932474
DeepCCS	[M-2H]-	174.973	30932474
DeepCCS	[M+Na]+	150.251	30932474
AllCCS	[M+H]+	130.8	32859911
AllCCS	[M+H-H2O]+	126.3	32859911
AllCCS	[M+NH4]+	134.9	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	134.0	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	138.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroisophorol	CC1CC(O)CC(C)(C)C1	1606.9	Standard polar	33892256
Dihydroisophorol	CC1CC(O)CC(C)(C)C1	1032.8	Standard non polar	33892256
Dihydroisophorol	CC1CC(O)CC(C)(C)C1	1064.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroisophorol,1TMS,isomer #1	CC1CC(O[Si](C)(C)C)CC(C)(C)C1	1115.8	Semi standard non polar	33892256
Dihydroisophorol,1TBDMS,isomer #1	CC1CC(O[Si](C)(C)C(C)(C)C)CC(C)(C)C1	1365.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dihydroisophorol EI-B (Non-derivatized)	splash10-0a4i-9300000000-244f20d79cae6e7e51b3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydroisophorol EI-B (Non-derivatized)	splash10-0a4i-9300000000-244f20d79cae6e7e51b3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroisophorol GC-MS (Non-derivatized) - 70eV, Positive	splash10-005a-9300000000-d7f74ae639a6d7f7fe0d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroisophorol GC-MS (1 TMS) - 70eV, Positive	splash10-006t-9700000000-98677d3381cb7d575de1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroisophorol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 10V, Positive-QTOF	splash10-004l-0900000000-1b18235f590ccbf61da2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 20V, Positive-QTOF	splash10-004l-3900000000-9026fc236779085d8ccf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 40V, Positive-QTOF	splash10-05nb-9200000000-8c94db27037d76dff113	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 10V, Negative-QTOF	splash10-0006-0900000000-524e1240924affa73e1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 20V, Negative-QTOF	splash10-0006-0900000000-ea27540a52f91b77ca9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 40V, Negative-QTOF	splash10-002g-9700000000-f11d1ab2b3606dbc2527	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 10V, Positive-QTOF	splash10-052f-9400000000-a2c3605f4c1480924a6d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 20V, Positive-QTOF	splash10-0a4i-9200000000-2d34cfe7f27ebee54314	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 40V, Positive-QTOF	splash10-0apl-9000000000-6b72ba755ce195c7f0a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 10V, Negative-QTOF	splash10-0006-0900000000-31a4c0b614cfbc7c3156	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 20V, Negative-QTOF	splash10-0006-0900000000-3962cd1a6f44a7191826	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisophorol 40V, Negative-QTOF	splash10-0006-0900000000-1bd0f7af6c59ba043f8e	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000708

KNApSAcK ID

Not Available

Chemspider ID

7997

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8298

PDB ID

Not Available

ChEBI ID

59065

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1023671

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Dihydroisophorol (HMDB0029557)

MOL for HMDB0029557 (Dihydroisophorol)

3D MOL for HMDB0029557 (Dihydroisophorol)

3D SDF for HMDB0029557 (Dihydroisophorol)

3D-SDF for HMDB0029557 (Dihydroisophorol)

PDB for HMDB0029557 (Dihydroisophorol)

3D PDB for HMDB0029557 (Dihydroisophorol)

SMILES for HMDB0029557 (Dihydroisophorol)

INCHI for HMDB0029557 (Dihydroisophorol)

Structure for HMDB0029557 (Dihydroisophorol)

3D Structure for HMDB0029557 (Dihydroisophorol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra