Showing Compound p-Menth-1-en-4-ol (FDB014601)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:22 UTC

Update date

2025-11-19 00:48:11 UTC

Primary ID

FDB014601

Secondary Accession Numbers

FDB007057
FDB003818

Chemical Information

FooDB Name

p-Menth-1-en-4-ol

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.

CAS Number

562-74-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(+-)-p-Menth-1-en-4-ol	ChEBI
1-Isopropyl-4-methylcyclohex-3-en-1-ol	ChEBI
1-Menthene-4-ol	ChEBI
1-Methyl-4-isopropyl-1-cyclohexen-4-ol	ChEBI
1-p-Menthen-4-ol	ChEBI
1-Para-menthen-4-ol	ChEBI
1-Terpinen-4-ol	ChEBI
4-Carvomenthenol	ChEBI
4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol	ChEBI
4-Methyl-1-isopropyl-3-cyclohexen-1-ol	ChEBI
alpha-Terpinen-4-ol	ChEBI
Terpene-4-ol	ChEBI
Terpin-4-en-1-ol	ChEBI
Terpinen-4-ol	ChEBI
Terpinene-4-ol	ChEBI
Terpinenol-4	ChEBI
Terpineol-4	ChEBI
a-Terpinen-4-ol	Generator
Α-terpinen-4-ol	Generator
1-Isopropyl-4-methyl-3-cyclohexen-1-ol	HMDB
4-Terpineol	HMDB
alpha -Terpinen-4-ol	HMDB
FEMA 2248	HMDB
Origanol	HMDB
p-Menth-1-en-4-ol	ChEBI
(R)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol	MeSH
α-Terpinen-4-ol	biospider
3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-	biospider
4-methyl-1-isopropyl-3-cyclohexen-1-ol	biospider

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H18O

IUPAC name

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

InChI Identifier

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

InChI Key

WRYLYDPHFGVWKC-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

154.253

Monoisotopic Molecular Weight

154.1357652

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Feces

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 77.87%; H 11.76%; O 10.37%	DFC
Melting Point	Not Available
Boiling Point	Boiling Pt : 209 oC
Experimental Water Solubility	Not Available
Experimental logP	3.26	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9200000000-42c59760ac8ce71b2738	2015-03-01	View Spectrum
GC-MS	1,4-Terpinenol, non-derivatized, GC-MS Spectrum	splash10-006x-9100000000-575f0430fad8f36207fc	Spectrum
GC-MS	1,4-Terpinenol, non-derivatized, GC-MS Spectrum	splash10-022l-9500000000-3f2e9ea1f5b3757fe0ee	Spectrum
GC-MS	1,4-Terpinenol, non-derivatized, GC-MS Spectrum	splash10-006x-9100000000-575f0430fad8f36207fc	Spectrum
GC-MS	1,4-Terpinenol, non-derivatized, GC-MS Spectrum	splash10-022l-9500000000-3f2e9ea1f5b3757fe0ee	Spectrum
Predicted GC-MS	1,4-Terpinenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014l-9200000000-dad36a705047932a9123	Spectrum
Predicted GC-MS	1,4-Terpinenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01xc-9310000000-a2afa37a32f9557366b3	Spectrum
Predicted GC-MS	1,4-Terpinenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,4-Terpinenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-9300000000-2b45d3d3c266789085c9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-675dc6e443ac10550c9f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-53271a36732e55f24c0d	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-6ab97f1e60330835e91d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-6900000000-04567bac2f7cdff17fbb	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-100r-9200000000-348297fc0a82a249f6ce	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-cf6571639c99834988f8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-08b8295cc319afc2225c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gw0-8900000000-e34fafe0d516af6cb77f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-8900000000-442df4d2c1c1a44d9f26	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0015-9300000000-08286b81fc833490c00b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d2fb56949f102920a8d5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-317e3f90e7716a16fe35	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9800000000-e9742125cfbf7b82348a	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35833

CRC / DFC (Dictionary of Food Compounds) ID

JSW58-R:JSW58-R

EAFUS ID

548

Dr. Duke ID

BIGG ID

Not Available

KNApSAcK ID

C00029544

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

562-74-3

GoodScent ID

rw1021751

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Allelopathic		Biochemicals that inhibit growth, survival, or reproduction in other organisms, with potential therapeutic applications in weed control, antimicrobial, and anticancer treatments, and key medical uses in developing novel pesticides, antibiotics, and chemotherapeutics.	DUKE
Anti acetylcholinesterase	38462	An agent that inhibits acetylcholinesterase, increasing acetylcholine levels. It enhances cholinergic transmission, used therapeutically to treat Alzheimer's disease, myasthenia gravis, and glaucoma, improving cognitive function, muscle strength, and reducing intraocular pressure.	DUKE
Anti-acne	50177	An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin.	DUKE
Anti-allergic	50857	An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.	DUKE
Anti-asthmatic	49167	An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-spasmodic	52217	An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.	DUKE
Anti-tussive	52217	An agent that suppresses coughing, reducing the frequency and severity of coughs. It works by targeting the brain's cough center, providing therapeutic relief for dry, irritating coughs. Key medical uses include managing coughs associated with colds, flu, and other respiratory conditions.	DUKE
Anti ulcer	49201	An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.	DUKE
Bacteriostatic	33282	An agent that inhibits bacterial growth, preventing multiplication without killing existing cells. It plays a biological role in controlling microbial populations. Therapeutically, bacteriostatics are used to treat infections, with key medical applications in dermatology, ophthalmology, and respiratory medicine, often in combination with other antimicrobials.	DUKE
Diuretic	35498	An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.	DUKE
Name	48318	flavor	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Herbicide	24527	A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.	DUKE
Insectifuge	24852	A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.	DUKE
Irritant		An agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.	DUKE
Nematicide	25491	An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Renoirritant		An agent that causes irritation or inflammation of kidney tissue, potentially used to study kidney disease mechanisms. Therapeutically, it may be used to model kidney injury, but its primary role is as a research tool rather than a treatment. Key medical uses include nephrotoxicity studies and understanding kidney disease pathology.	DUKE
Spermicide		A contraceptive substance that destroys sperm, inserted vaginally prior to intercourse to prevent pregnancy, serving as a non-hormonal birth control method.	DUKE
Vulnerary	73336	An agent that promotes wound healing, tissue repair, and skin regeneration. It facilitates the biological process of recovery, reducing inflammation and infection. Therapeutically, vulneraries are used to treat cuts, burns, ulcers, and other skin injuries, supporting the body's natural healing mechanisms and minimizing scarring.	DUKE
Anti neoplastic	35610	An agent that inhibits or suppresses the growth and proliferation of cancer cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce apoptosis, prevent tumor progression, and enhance patient survival. Key medical uses include chemotherapy, radiation therapy, and targeted therapy for various types of cancer, such as leukemia, breast, lung, and colon cancer.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
turpentine	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
nutmeg	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
must	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
pepper	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earth	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.