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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:09:21 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036087

Secondary Accession Numbers

HMDB36087

Metabolite Identification

Common Name

(R)-p-Mentha-1,8-dien-7-ol

Description

(R)-p-Mentha-1,8-dien-7-ol, also known as (4R)-perillyl alcohol, 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 (R)-p-Mentha-1,8-dien-7-ol.

Structure

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

COMPND    HMDB0036087
HETATM    1  C1  UNL     1      -2.930   1.208  -0.209  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.278   0.084  -0.062  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.020  -1.214  -0.038  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.805  -0.009   0.089  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.224  -0.893  -0.958  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.255  -0.844  -0.894  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.920   0.027  -0.192  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.433  -0.045  -0.224  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.826  -1.088  -1.044  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.247   1.070   0.625  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.128   1.341   0.055  1.00  0.00           C  
HETATM   12  H1  UNL     1      -4.005   1.194  -0.313  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.465   2.186  -0.236  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.940  -1.122   0.572  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.250  -1.505  -1.088  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.428  -2.035   0.399  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.601  -0.447   1.088  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.573  -1.930  -0.759  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.513  -0.559  -1.983  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.827  -1.600  -1.484  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.819  -0.212   0.791  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.856   0.892  -0.638  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.701  -0.904  -2.003  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.077   0.616   1.644  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.851   1.981   0.736  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.000   1.727  -0.981  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.652   2.084   0.692  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   18   19
CONECT    6    7    7   20
CONECT    7    8   10
CONECT    8    9   21   22
CONECT    9   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-Perillyl alcohol	ChEBI
(4R)-Perillyl alcohol	ChEBI
(R)-Perillyl alcohol	ChEBI
D-Perillyl alcohol	ChEBI
(R)-(+)-Perillyl alcohol	HMDB
(R)-4-(1-Methylethenyl)-1-cyclohexene-1-methanol	HMDB
4-(1-Methylethenyl)-(4R)-1-cyclohexene-1-methanol	HMDB
(-)-p-Mentha-1,8-dien-7-ol	MeSH
(S)-Perillyl alcohol	MeSH
p-Mentha-1,8-dien-7-ol	MeSH
4-Isopropenyl-cyclohex-1-ene-1-methanol	MeSH
Perilla alcohol, (S)-isomer	MeSH
Dihydrocuminyl alcohol	MeSH
Perilla alcohol	MeSH
Perilla alcohol, (R)-isomer	MeSH
Cyclohex-1-ene-1-methanol, 4(1-methylethenyl)	MeSH
Perillyl alcohol	MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

[(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

Traditional Name

[(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

CAS Registry Number

57717-97-2

SMILES

CC(=C)[C@@H]1CCC(CO)=CC1

InChI Identifier

InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m0/s1

InChI Key

NDTYTMIUWGWIMO-JTQLQIEISA-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
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036088)
Membrane (HMDB: HMDB0036088)

Source

Exogenous

Exogenous (HMDB: HMDB0036088)

Endogenous

Endogenous (HMDB: HMDB0036088)

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	119.00 to 121.00 °C. @ 11.00 mm Hg	The Good Scents Company Information System
Water Solubility	471 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.17	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.9 g/L	ALOGPS
logP	2.5	ALOGPS
logP	1.94	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	16.86	ChemAxon
pKa (Strongest Basic)	-2	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	2	ChemAxon
Refractivity	48.26 m³·mol⁻¹	ChemAxon
Polarizability	18.18 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]+	135.559	31661259
DarkChem	[M-H]-	131.791	31661259
DeepCCS	[M+H]+	142.007	30932474
DeepCCS	[M-H]-	139.498	30932474
DeepCCS	[M-2H]-	174.913	30932474
DeepCCS	[M+Na]+	149.864	30932474
AllCCS	[M+H]+	133.8	32859911
AllCCS	[M+H-H2O]+	129.3	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.1	32859911
AllCCS	[M-H]-	137.5	32859911
AllCCS	[M+Na-2H]-	139.0	32859911
AllCCS	[M+HCOO]-	140.8	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.	4.41 minutes	32390414
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.	4.95 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7119 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.32 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-p-Mentha-1,8-dien-7-ol	CC(=C)[C@@H]1CCC(CO)=CC1	1996.8	Standard polar	33892256
(R)-p-Mentha-1,8-dien-7-ol	CC(=C)[C@@H]1CCC(CO)=CC1	1263.1	Standard non polar	33892256
(R)-p-Mentha-1,8-dien-7-ol	CC(=C)[C@@H]1CCC(CO)=CC1	1286.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-p-Mentha-1,8-dien-7-ol,1TMS,isomer #1	C=C(C)[C@H]1CC=C(CO[Si](C)(C)C)CC1	1368.0	Semi standard non polar	33892256
(R)-p-Mentha-1,8-dien-7-ol,1TMS,isomer #1	C=C(C)[C@H]1CC=C(CO[Si](C)(C)C)CC1	1368.0	Semi standard non polar	33892256
(R)-p-Mentha-1,8-dien-7-ol,1TBDMS,isomer #1	C=C(C)[C@H]1CC=C(CO[Si](C)(C)C(C)(C)C)CC1	1601.0	Semi standard non polar	33892256
(R)-p-Mentha-1,8-dien-7-ol,1TBDMS,isomer #1	C=C(C)[C@H]1CC=C(CO[Si](C)(C)C(C)(C)C)CC1	1601.0	Semi standard non polar	33892256

Spectra

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

FDB014924

KNApSAcK ID

C00010884

Chemspider ID

9963072

KEGG Compound ID

Not Available

BioCyc ID

CPD-17084

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11788398

PDB ID

Not Available

ChEBI ID

145806

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1108581

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 (R)-p-Mentha-1,8-dien-7-ol (HMDB0036087)

MOL for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

3D MOL for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

3D SDF for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

3D-SDF for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

PDB for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

3D PDB for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

SMILES for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

INCHI for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

Structure for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

3D Structure for HMDB0036087 ((R)-p-Mentha-1,8-dien-7-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized