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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:37:06 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034715

Secondary Accession Numbers

HMDB34715

Metabolite Identification

Common Name

p-Mentha-1(6),8-dien-3-ol

Description

p-Mentha-1(6),8-dien-3-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 significant number of articles have been published on p-Mentha-1(6),8-dien-3-ol.

Structure

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

COMPND    HMDB0034715
HETATM    1  C1  UNL     1      -3.049   0.024  -0.517  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.754   0.150  -0.276  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.291   1.436   0.325  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.814  -0.957  -0.597  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.148  -0.592  -1.706  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.169   0.340  -1.226  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.622   0.261  -0.002  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.664   1.241   0.426  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.156  -0.739   0.958  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.072  -1.471   0.594  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.970  -1.449   1.680  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.721   0.827  -0.282  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.455  -0.885  -0.953  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.152   2.077   0.596  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.654   2.023  -0.348  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.771   1.236   1.308  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.423  -1.797  -0.991  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.677  -1.553  -1.971  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.368  -0.279  -2.619  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.541   1.101  -1.917  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.649   1.424   1.510  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.516   2.222  -0.075  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.678   0.882   0.094  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.031  -0.221   1.946  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.998  -1.479   1.098  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.141  -2.569   0.435  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.496  -1.253   2.508  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   10   17
CONECT    5    6   18   19
CONECT    6    7    7   20
CONECT    7    8    9
CONECT    8   21   22   23
CONECT    9   10   24   25
CONECT   10   11   26
CONECT   11   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methyl-6-(1-methylethenyl)-3-cyclohexen-1-ol, 9ci	HMDB
P-Mentha-1,8-dien-5-ol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

3-methyl-6-(prop-1-en-2-yl)cyclohex-3-en-1-ol

Traditional Name

3-methyl-6-(prop-1-en-2-yl)cyclohex-3-en-1-ol

CAS Registry Number

20019-62-9

SMILES

CC(=C)C1CC=C(C)CC1O

InChI Identifier

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

InChI Key

ZTDBSRAQWPKHIO-UHFFFAOYSA-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
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0034715)

Food

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	372.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.450 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.19 g/L	ALOGPS
logP	2.45	ALOGPS
logP	1.91	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	19.37	ChemAxon
pKa (Strongest Basic)	-0.89	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	48.07 m³·mol⁻¹	ChemAxon
Polarizability	18.37 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]+	135.331	31661259
DarkChem	[M-H]-	131.381	31661259
DeepCCS	[M+H]+	139.997	30932474
DeepCCS	[M-H]-	137.352	30932474
DeepCCS	[M-2H]-	173.525	30932474
DeepCCS	[M+Na]+	148.927	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.2	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.1	32859911
AllCCS	[M-H]-	136.4	32859911
AllCCS	[M+Na-2H]-	137.9	32859911
AllCCS	[M+HCOO]-	139.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.45 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6003 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.64 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1866.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	353.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	76.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	398.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	550.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	920.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	355.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1005.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	410.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	26.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Mentha-1(6),8-dien-3-ol	CC(=C)C1CC=C(C)CC1O	1663.9	Standard polar	33892256
p-Mentha-1(6),8-dien-3-ol	CC(=C)C1CC=C(C)CC1O	1183.7	Standard non polar	33892256
p-Mentha-1(6),8-dien-3-ol	CC(=C)C1CC=C(C)CC1O	1199.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-Mentha-1(6),8-dien-3-ol,1TMS,isomer #1	C=C(C)C1CC=C(C)CC1O[Si](C)(C)C	1258.4	Semi standard non polar	33892256
p-Mentha-1(6),8-dien-3-ol,1TBDMS,isomer #1	C=C(C)C1CC=C(C)CC1O[Si](C)(C)C(C)(C)C	1497.6	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 - p-Mentha-1(6),8-dien-3-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udu-9400000000-347d1697d554664b7c94	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Mentha-1(6),8-dien-3-ol GC-MS (1 TMS) - 70eV, Positive	splash10-05a9-9520000000-86fb25fa6b661eb47edc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Mentha-1(6),8-dien-3-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 - p-Mentha-1(6),8-dien-3-ol 10V, Positive-QTOF	splash10-0f79-1900000000-c405df4fd0f5b254c851	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 20V, Positive-QTOF	splash10-0f79-6900000000-3e0157297df47bee86c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 40V, Positive-QTOF	splash10-0pvi-9100000000-ff681d24b2af18453aba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 10V, Negative-QTOF	splash10-0udi-0900000000-c3809af54a4a440e63aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 20V, Negative-QTOF	splash10-0udi-0900000000-5d82677cfa4e5710b470	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 40V, Negative-QTOF	splash10-0btl-6900000000-5dacea1244d861f13ef5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 20V, Negative-QTOF	splash10-0ue9-0900000000-fa4349f879d2333c1571	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 40V, Negative-QTOF	splash10-014i-9800000000-ba7cdd1975b283687aea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 10V, Positive-QTOF	splash10-03dr-4900000000-4c6dd37ca6dd1eb453ed	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 20V, Positive-QTOF	splash10-014m-9200000000-a4e64d913e552910e058	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-1(6),8-dien-3-ol 40V, Positive-QTOF	splash10-0006-9000000000-6e4533d1d749320bedbc	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB013251

KNApSAcK ID

Not Available

Chemspider ID

35013776

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14844669

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1126721

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 p-Mentha-1(6),8-dien-3-ol (HMDB0034715)

MOL for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

3D MOL for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

3D SDF for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

3D-SDF for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

PDB for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

3D PDB for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

SMILES for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

INCHI for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

Structure for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

3D Structure for HMDB0034715 (p-Mentha-1(6),8-dien-3-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra