Terpinen-4-ol (YMDB01790)

Identification

YMDB ID

YMDB01790

Name

Terpinen-4-ol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

p-Menth-1-en-4-ol, also known as terpinen-4-ol or 1-para-menthen-4-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-Menth-1-en-4-ol.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-Isopropyl-4-methyl-3-cyclohexen-1-ol
1-Methyl-4-isopropyl-1-cyclohexen-4-ol
1-methyl-4-isopropyl-1-cyclohexen-4-ol (4-terpineol)
1-para-Menthen-4-ol
1-Terpinen-4-ol
3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-
3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, (R)-
3-Cyclohexen-1-ol, 4-methyl-1-[methylethyl]-
4-Carvomenthenol
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol
4-Methyl-1-(methylethyl)-3-cyclohexen-1-ol
4-methyl-1-isopropyl-3-cyclohexen-1-ol
4-Terpeneol
4-Terpinenol
4-Terpineol
alpha-Terpinen-4-ol
I-4-terpineol
p-Menth-1-en-4-ol
p-Menth-1-en-4-ol, (R)-(-)-
para-Menth-1-en-4-ol
Terpene-4-ol
Terpin-4-en-1-ol
Terpin-4-ol
Terpine-4-ol
Terpinen-4-ol [4S-(+), 4R-(-)]
Terpinene-4-ol
Terpinenol-4
Terpinenolu-4
Terpineol-4
(+-)-p-Menth-1-en-4-ol
1-Isopropyl-4-methylcyclohex-3-en-1-ol
1-Menthene-4-ol
1-p-Menthen-4-ol
Terpinen-4-ol
a-Terpinen-4-ol
Α-terpinen-4-ol
alpha -Terpinen-4-ol
FEMA 2248
Origanol
(R)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol

CAS number

562-74-3

Weight

Average: 154.2493
Monoisotopic: 154.135765198

InChI Key

WRYLYDPHFGVWKC-UHFFFAOYSA-N

InChI

InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3

IUPAC Name

4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol

Traditional IUPAC Name

terpinen-4-ol

Chemical Formula

C₁₀H₁₈O

SMILES

CC(C)C1(O)CCC(C)=CC1

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

tertiary alcohol (CHEBI:78884 )
terpineol (CHEBI:78884 )
Menthane monoterpenoids (C17073 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	3.26 [GRIFFIN,S ET AL. (1999)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	2.5 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.33	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	20	ChemAxon
pKa (Strongest Basic)	-0.61	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	48.31 m³·mol⁻¹	ChemAxon
Polarizability	18.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Earth	FDB014601
Must	FDB014601
Musty	FDB014601
Nutmeg	FDB014601
Pepper	FDB014601
Sweet	FDB014601
Turpentine	FDB014601
Woody	FDB014601

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006x-9100000000-575f0430fad8f36207fc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-022l-9500000000-3f2e9ea1f5b3757fe0ee	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006x-9100000000-575f0430fad8f36207fc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-022l-9500000000-3f2e9ea1f5b3757fe0ee	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-9200000000-dad36a705047932a9123	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01xc-9310000000-a2afa37a32f9557366b3	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-9300000000-2b45d3d3c266789085c9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-675dc6e443ac10550c9f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-53271a36732e55f24c0d	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-6ab97f1e60330835e91d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-6900000000-04567bac2f7cdff17fbb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-100r-9200000000-348297fc0a82a249f6ce	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-cf6571639c99834988f8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-08b8295cc319afc2225c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gw0-8900000000-e34fafe0d516af6cb77f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-8900000000-442df4d2c1c1a44d9f26	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0015-9300000000-08286b81fc833490c00b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d2fb56949f102920a8d5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-317e3f90e7716a16fe35	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9800000000-e9742125cfbf7b82348a	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9200000000-42c59760ac8ce71b2738	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	78884
HMDB ID	HMDB0035833
Pubchem Compound ID	11230
Kegg ID	C17073
ChemSpider ID	10756
FOODB ID	FDB014601
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xacc05664>