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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:59:41 UTC

Update Date

2023-02-21 17:24:34 UTC

HMDB ID

HMDB0035054

Secondary Accession Numbers

HMDB35054

Metabolite Identification

Common Name

(1S,4R)-p-Mentha-2,8-dien-1-ol

Description

(1S,4R)-p-Mentha-2,8-dien-1-ol 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. Based on a literature review a small amount of articles have been published on (1S,4R)-p-Mentha-2,8-dien-1-ol.

Structure

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

COMPND    HMDB0035054
HETATM    1  C1  UNL     1       2.761   0.779   1.049  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.288  -0.227   0.345  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.068  -1.474   0.126  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.919  -0.141  -0.268  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.036  -1.210   0.218  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.250  -1.058   0.418  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.931   0.230   0.167  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.176  -0.089  -0.667  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.391   0.795   1.356  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.079   1.174  -0.622  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.285   1.191   0.061  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.753   0.691   1.481  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.193   1.671   1.201  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.130  -1.324   0.342  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.890  -1.771  -0.940  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.660  -2.275   0.789  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.028  -0.206  -1.372  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.474  -2.197   0.427  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.854  -1.921   0.788  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.988   0.601  -0.380  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.502  -1.128  -0.496  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.901   0.006  -1.756  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.044   1.510   1.118  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.492   2.209  -0.624  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.908   0.812  -1.655  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.147   1.305   1.136  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.885   2.047  -0.318  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6    6   18
CONECT    6    7   19
CONECT    7    8    9   10
CONECT    8   20   21   22
CONECT    9   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-cis-P-Mentha-2,8-dien-1-ol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol

Traditional Name

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol

CAS Registry Number

22972-51-6

SMILES

CC(=C)[C@@H]1CC[C@](C)(O)C=C1

InChI Identifier

InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10+/m0/s1

InChI Key

MKPMHJQMNACGDI-VHSXEESVSA-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
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	18 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	448.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.97 g/L	ALOGPS
logP	2.58	ALOGPS
logP	2.03	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	18.25	ChemAxon
pKa (Strongest Basic)	-1.4	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	48.35 m³·mol⁻¹	ChemAxon
Polarizability	18 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]+	138.061	31661259
DarkChem	[M-H]-	132.584	31661259
DeepCCS	[M+H]+	136.186	30932474
DeepCCS	[M-H]-	133.79	30932474
DeepCCS	[M-2H]-	167.673	30932474
DeepCCS	[M+Na]+	142.261	30932474
AllCCS	[M+H]+	131.9	32859911
AllCCS	[M+H-H2O]+	127.4	32859911
AllCCS	[M+NH4]+	136.1	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	137.3	32859911
AllCCS	[M+HCOO]-	139.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1S,4R)-p-Mentha-2,8-dien-1-ol	CC(=C)[C@@H]1CC[C@](C)(O)C=C1	1619.5	Standard polar	33892256
(1S,4R)-p-Mentha-2,8-dien-1-ol	CC(=C)[C@@H]1CC[C@](C)(O)C=C1	1126.2	Standard non polar	33892256
(1S,4R)-p-Mentha-2,8-dien-1-ol	CC(=C)[C@@H]1CC[C@](C)(O)C=C1	1131.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1S,4R)-p-Mentha-2,8-dien-1-ol,1TMS,isomer #1	C=C(C)[C@H]1C=C[C@@](C)(O[Si](C)(C)C)CC1	1268.6	Semi standard non polar	33892256
(1S,4R)-p-Mentha-2,8-dien-1-ol,1TBDMS,isomer #1	C=C(C)[C@H]1C=C[C@@](C)(O[Si](C)(C)C(C)(C)C)CC1	1506.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-9500000000-e23ae80878d4e866f016	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol GC-MS (1 TMS) - 70eV, Positive	splash10-059l-9320000000-34c08eff2d1d5871315e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 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 - (1S,4R)-p-Mentha-2,8-dien-1-ol 10V, Positive-QTOF	splash10-0f79-0900000000-6e5429b970b50045594f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 20V, Positive-QTOF	splash10-0f79-5900000000-73d286d3392ad6eec010	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 40V, Positive-QTOF	splash10-0gb9-9200000000-55c6fe5f6141ae369840	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 10V, Negative-QTOF	splash10-0udi-0900000000-a931fddf6f76ffb52f18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 20V, Negative-QTOF	splash10-0udi-0900000000-e7155fded3abd51b6ea0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 40V, Negative-QTOF	splash10-0k9l-5900000000-f8457f95373cdd01f3e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 10V, Positive-QTOF	splash10-000m-8900000000-ca2176873451eccadaa1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 20V, Positive-QTOF	splash10-002f-9000000000-08f9899643afc6dea2d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 40V, Positive-QTOF	splash10-0fvi-9000000000-dd4d2e99b68d0c5cb5a6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 20V, Negative-QTOF	splash10-0ue9-1900000000-70633168765f61f178b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,4R)-p-Mentha-2,8-dien-1-ol 40V, Negative-QTOF	splash10-014i-9300000000-51890339d15dded3c59d	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB013676

KNApSAcK ID

C00010887

Chemspider ID

9280686

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11105550

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1847361

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (1S,4R)-p-Mentha-2,8-dien-1-ol (HMDB0035054)

MOL for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

3D MOL for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

3D SDF for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

3D-SDF for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

PDB for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

3D PDB for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

SMILES for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

INCHI for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

Structure for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

3D Structure for HMDB0035054 ((1S,4R)-p-Mentha-2,8-dien-1-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra