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4-carvomenthenol

4-carvomenthenol, also known as terpinen-4-ol, is a natural terpene alcohol used in flavors and fragrances with spicy, woody, and cooling characteristics.
Chemical Structure

General Material Description

4-carvomenthenol, commonly known as terpinen-4-ol, is a naturally occurring monoterpene alcohol with the molecular formula C10H18O. It appears as a colorless to pale yellow liquid and exhibits characteristic woody, spicy, and menthol-like aroma traits. Terpinen-4-ol is a significant component in many essential oils and presents a range of sensory notes, including cooling and earthy aspects. This compound is listed in controlled vocabulary databases such as ChEBI. It is commonly sourced from the essential oils of various plants, including tea tree, marjoram, and eucalyptus.

Occurrence, Applicability & Uses

4-carvomenthenol is widely found in nature within numerous essential oils derived from plants such as tea tree (Melaleuca), marjoram, eucalyptus, oregano, and many spices. It occurs in varying concentrations, for example approximately 1.5% in cajuput oil and between trace to several percent in other botanical oils. The compound is employed primarily as a flavor and fragrance agent, contributing woody, spicy, herbal, and cooling notes in formulations. Its applicability is supported by standards such as FEMA (US), where it holds the number 2248. It serves as a replacer for cardamom and tarragon oils in flavoring and enhances aromatic profiles in both food and cosmetic products.

Physico-Chemical Properties Summary

4-carvomenthenol exhibits moderate volatility with a flash point around 79°C (175°F) and a logP value of approximately 3.26, indicating moderate lipophilicity suitable for fragrance and flavor applications. At 25°C, its density ranges between 0.928 and 0.934 g/mL. It shows slight water solubility, estimated at 386.6 mg/L, and good solubility in alcohols. Due to its physicochemical traits, it is stable when stored in cool, dry, and dark conditions within tightly sealed containers. The compound’s sensory efficacy is influenced by these properties, enabling substantive impact in formulations over extended periods of time.

FAQ

What is 4-carvomenthenol and how is it related to terpinen-4-ol?
4-carvomenthenol is a naturally occurring monoterpene alcohol. Terpinen-4-ol is a trivial and widely used synonym for the same chemical compound. Both names refer to a substance with the molecular formula C10H18O that possesses notable woody, spicy, and cooling aromatic properties. It is present in various essential oils and is used in flavor and fragrance formulations.
Where is 4-carvomenthenol found and what are its typical uses?
It occurs naturally in essential oils of plants such as tea tree, marjoram, eucalyptus, oregano, and several spice oils. Its concentration varies across these sources. 4-carvomenthenol is used as a flavoring agent to impart woody, spicy, and citrus-like notes and also serves as a fragrance ingredient with cooling and herbal characters. It can replace cardamom, tarragon, and thyme oils in formulations.
What regulations and safety considerations apply to 4-carvomenthenol?
4-carvomenthenol is recognized under FEMA (US) with the number 2248 and assessed by IFRA (Global) for safe usage levels, recommending maximum skin concentrations around 0.13% in fine fragrances and up to 5% in fragrance concentrates. It is classified as harmful if swallowed and irritating to eyes and skin per European safety data, thus requiring proper handling and protective measures. It is also listed by JECFA with specific food flavoring evaluations.

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Literature & References

Leffingwell:Chirality or Article
4-methyl-1-propan-2-ylcyclohex-3-en-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:562-74-3
Pubchem (cid):11230
Pubchem (sid):134978014
Flavornet:562-74-3
Pherobase:View
Publications by PubMed
The Biological Activity and Composition of the Essential Oil of Sclerorhachis leptoclada (Asteraceae-Anthemideae) from Iran.
Study on cinnamomum oils: compositional pattern of seven species grown in Vietnam.
Chemical Constituents and Activities of the Essential Oil from Myristica fragrans against Cigarette Beetle Lasioderma serricorne.
Essential oils from Schinus species of northwest Argentina: Composition and antifungal activity.
Investigation of terpinen-4-ol effects on vascular smooth muscle relaxation.
Monoterpenoid terpinen-4-ol exhibits anticonvulsant activity in behavioural and electrophysiological studies.
Essential oil from blackcurrant buds as chemotaxonomy marker and antimicrobial agent.
Molecular and phytochemical investigation of Angelica dahurica and Angelica pubescentis essential oils and their biological activity against Aedes aegypti, Stephanitis pyrioides, and Colletotrichum species.
Essential oil from leaves of Liquidambar formosana ameliorates inflammatory response in lipopolysaccharide-activated mouse macrophages.
In-vitro assessment of antioxidant and antimicrobial activities of methanol extracts and essential oil of Thymus hirtus sp. algeriensis.
Activity of tea tree (Melaleuca alternifolia) essential oil against L3 larvae of Anisakis simplex.
Terpinen-4-ol and alpha-terpineol (tea tree oil components) inhibit the production of IL-1β, IL-6 and IL-10 on human macrophages.
Toxicity of hiba oil constituents and spray formulations to American house dust mites and copra mites.
Influence of culture conditions on the biotransformation of (+)-limonene by Aspergillus niger.
Chemical composition of the essential oil from Croton kimosorum, an endemic species to Madagascar.
Antioxidant activity of fractions from oregano essential oils obtained by molecular distillation.
Exocrine secretions of wheel bugs (Heteroptera: Reduviidae: Arilus spp.): clarification and chemistry.
Essential oil from lemon peels inhibit key enzymes linked to neurodegenerative conditions and pro-oxidant induced lipid peroxidation.
Terpinen-4-ol induces autophagic and apoptotic cell death in human leukemic HL-60 cells.
Chemical analysis and calcium channel blocking activity of the essential oil of Perovskia abrotanoides.
Terpinen-4-ol is the Most Active Ingredient of Tea Tree Oil to Kill Demodex Mites.
In vitro genotoxicity of Melaleuca alternifolia essential oil in human lymphocytes.
Comparative in vivo antioxidant levels in Schistosoma mansoni infected mice treated with praziquantel or the essential oil of Melaleuca armillaris leaves.
Sedative and anesthetic activities of the essential oils of Hyptis mutabilis (Rich.) Briq. and their isolated components in silver catfish (Rhamdia quelen).
Antimicrobial activity of essential oils and five terpenoid compounds against Campylobacter jejuni in pure and mixed culture experiments.
Evaluation of volatiles from Ampelopsis brevipedunculata var. heterophylla using GC-olfactometry, GC-MS and GC-pulsed flame photometric detector.
Disruption of the PI3K/AKT/mTOR signaling cascade and induction of apoptosis in HL-60 cells by an essential oil from Monarda citriodora.
Aroma-impact compounds in dried spice as a quality index using solid phase microextraction with olfactometry and comprehensive two-dimensional gas chromatography.
Melaleuca alternifolia concentrate inhibits in vitro entry of influenza virus into host cells.
Vibrational spectroscopy as a rapid quality control method for Melaleuca alternifolia cheel (tea tree oil).
Mosquito larvicidal activity of thymol from essential oil of Coleus aromaticus Benth. against Culex tritaeniorhynchus, Aedes albopictus, and Anopheles subpictus (Diptera: Culicidae).
Volatile constituents of Saussurea costus roots cultivated in Uttarakhand Himalayas, India.
Chemical composition, antimicrobial properties and toxicity evaluation of the essential oil of Cupressus lusitanica Mill. leaves from Cameroon.
Isolation of terpenoids from Pimpinella anisum essential oil by high-performance counter-current chromatography.
Composition and in vitro anticancer activities of the leaf essential oil of Neolitsea variabillima from Taiwan.
Whitening and antioxidant activities of bornyl acetate and nezukol fractionated from Cryptomeria japonica essential oil.
In vitro and in vivo anti-tobacco mosaic virus activities of essential oils and individual compounds.
Encapsulation of plai oil/2-hydroxypropyl-β-cyclodextrin inclusion complexes in polyvinylpyrrolidone (PVP) electrospun nanofibers for topical application.
Suppression of inflammatory reactions by terpinen-4-ol, a main constituent of tea tree oil, in a murine model of oral candidiasis and its suppressive activity to cytokine production of macrophages in vitro.
Volatile constituents of Pinus roxburghii from Nepal.
Phytochemical diversity of Murraya koenigii (L.) Spreng. from Western Himalaya.
Behavioural and electroantennogram responses of the stable fly (Stomoxys calcitrans L.) to plant essential oils and their mixtures with attractants.
Essential oils from five species of Annonaceae from Vietnam.
Effect of habituation to tea tree (Melaleuca alternifolia) oil on the subsequent susceptibility of Staphylococcus spp. to antimicrobials, triclosan, tea tree oil, terpinen-4-ol and carvacrol.
Composition and in-vitro cytotoxic activities of the leaf essential oil of Beilschmiedia erythrophloia from Taiwan.
Plasma and dermal pharmacokinetics of terpinen-4-ol in rats following intravenous administration.
Southern pine beetle, Dendroctonus frontalis, antennal and behavioral responses to nonhost leaf and bark volatiles.
[Effects of inhibitory activity on mycelial growth of Candida albicans and therapy for murine oral candidiasis by the combined use of terpinen-4-ol and a middle-chain fatty acid, capric acid].
Gold nanoparticles-peptide based gas sensor arrays for the detection of food aromas.
Synergistic combinations of high hydrostatic pressure and essential oils or their constituents and their use in preservation of fruit juices.
Chemical and biological study on the essential oil of Artemisia caerulescens L. ssp. densiflora (Viv.).
Chemical compositions of essential oils from Xyloselinum vietnamense and X. selinum leonidii.
Antifungal and antibacterial activity of the essential oil of Chamaecyparis lawsoniana from Spain.
Effect of heat treatments on the essential oils of kumquat (Fortunella margarita Swingle).
Chemical diversity of wild growing Origanum majorana in Cyprus.
Cleavage of α-dicarbonyl compounds by terpene hydroperoxide.
Dermal pharmacokinetics of Terpinen-4-ol following topical administration of Zingiber cassumunar (plai) oil.
Distillation time alters essential oil yield, composition, and antioxidant activity of male Juniperus scopulorum trees.
A review of applications of tea tree oil in dermatology.
Induction of intrinsic and extrinsic apoptosis pathways in the human leukemic MOLT-4 cell line by terpinen-4-ol.
Comparison of chemical composition and antibacterial activity of lavender varieties from Poland.
Chemical composition, olfactory analysis and antibacterial activity of Thymus vulgaris chemotypes geraniol, 4-thujanol/terpinen-4-ol, thymol and linalool cultivated in southern France.
Plant essential oils and mastitis disease: their potential inhibitory effects on pro-inflammatory cytokine production in response to bacteria related inflammation.
Use of multiparameter flow cytometry to determine the effects of monoterpenoids and phenylpropanoids on membrane polarity and permeability in staphylococci and enterococci.
Culture conditions and salt effects on essential oil composition of sweet marjoram (Origanum majorana) from Tunisia.
Anti-plasmodial and insecticidal activities of the essential oils of aromatic plants growing in the Mediterranean area.
Antifungal, cytotoxic, and immunomodulatory properties of tea tree oil and its derivative components: potential role in management of oral candidosis in cancer patients.
Thymol nanospheres as an effective anti-bacterial agent.
The essential oil of Melaleuca alternifolia (tea tree oil) and its main component, terpinen-4-ol protect mice from experimental oral candidiasis.
A mobile olfactometer for fMRI-studies.
In Vitro Cytotoxic Potential of Essential Oils of Eucalyptus benthamii and Its Related Terpenes on Tumor Cell Lines.
Characterization, antibiofilm, and mechanism of action of novel PEG-stabilized lipid nanoparticles loaded with terpinen-4-ol.
Tea tree oil-induced transcriptional alterations in Staphylococcus aureus.
Fragrant volatile oil composition of Nutmeg Geranium (Pelargonium × fragrans Willd.) from India.
Chemical composition and amoebicidal activity of Croton pallidulus, Croton ericoides, and Croton isabelli (Euphorbiaceae) essential oils.
A comprehensive review of vaginitis phytotherapy.
Tea tree oil as a novel antipsoriasis weapon.
Degradation of terpenes and terpenoids from Mediterranean rangelands by mixed rumen bacteria in vitro.
Extraction and separation of volatile and fixed oils from seeds of Myristica fragrans by supercritical CO₂: chemical composition and cytotoxic activity on Caco-2 cancer cells.
Composition of the essential oils and antibacterial activities of Hymenocrater yazdianus, Stachys obtusicrena and Nepeta asterotricha three Labiatae herbs growing wild in Iran.
Comparative GC/MS analysis of essential oils extracted by 3 methods from the bud of Citrus aurantium L. var. amara Engl.
Acaricidal activities of Santolina africana and Hertia cheirifolia essential oils against the two-spotted spider mite (Tetranychus urticae).
Bioactivity of tea tree oil from Melaleuca alternifolia against sheep lice (Bovicola ovis Schrank) in vitro.
In vitro antifungal activity of terpinen-4-ol, eugenol, carvone, 1,8-cineole (eucalyptol) and thymol against mycotoxigenic plant pathogens.
Antimicrobial investigation of Linum usitatissimum for the treatment of acne.
Metabolism of (+)-terpinen-4-ol by cytochrome P450 enzymes in human liver microsomes.
Toxicity of essential and non-essential oils against the chewing louse, Bovicola (Werneckiella) ocellatus.
Steam sauna and mother roasting in Lao PDR: practices and chemical constituents of essential oils of plant species used in postpartum recovery.
In vitro activities of natural products against oral Candida isolates from denture wearers.
Multidimensional enantio gas chromtography/mass spectrometry and gas chromatography-combustion-isotopic ratio mass spectrometry for the authenticity assessment of lime essential oils (C. aurantifolia Swingle and C. latifolia Tanaka).
Effects of Melaleuca alternifolia (tea tree) essential oil and the major monoterpene component terpinen-4-ol on the development of single- and multistep antibiotic resistance and antimicrobial susceptibility.
Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes.
Volatile constituents of Origanum vulgare L., 'thymol' chemotype: variability in North India during plant ontogeny.
Distribution and chemical polymorphism of the essential oils of Achillea cartilaginea growing wild in Lithuania.
Chemical composition and herbicidal activity of the essential oil from a Cistus ladanifer L. population from Spain.
Chemical composition and antimicrobial activity of the essential oil of Anthemis altissima L. var. altissima.
Simultaneous determination of eight active components in Houttuynia cordata injection and its quality control in productive process.
Insecticidal and repellent effects of tea tree (Melaleuca alternifolia) oil against Lucilia cuprina.
Contact toxicity, feeding reduction, and repellency of essential oils from three plants from the ginger family (Zingiberaceae) and their major components against Sitophilus zeamais and Tribolium castaneum.
Chemical composition and acaricidal properties of Deverra scoparia essential oil (Araliales: Apiaceae) and blends of its major constituents against Tetranychus urticae (Acari: Tetranychidae).
Analysis of human male armpit sweat after fenugreek ingestion: Characterisation of odour active compounds by gas chromatography coupled to mass spectrometry and olfactometry.
Citrus essential oil of Nigeria. Part V: Volatile constituents of sweet orange leaf oil (Citrus sinensis).
Salt effects on Origanum majorana fatty acid and essential oil composition.
Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo.
Volatile compounds in the stem bark of Sclerocarya birrea (Anacardiaceae) possess antimicrobial activity against drug-resistant strains of Helicobacter pylori.
Insecticidal effect and chemical composition of the volatile oil from Bergenia ligulata.
Effect of the method of preparation on the composition and cytotoxic activity of the essential oil of Pituranthos tortuosus.
Antibiofilm activity of selected plant essential oils and their major components.
Essential oils of medicinal plants from the central andes of Argentina: chemical composition, and antifungal, antibacterial, and insect-repellent activities.
The inhibitory effect of Zingiber corallinum Hance essential oil on drug-resistant bacteria and evaluation of its acute toxicity.
2-undecanone rich leaf essential oil from Zanthoxylum armatum.
Comparison of Eucalyptus cinerea essential oils produced by hydrodistillation and supercritical carbon dioxide extraction.
Seasonal variation in the chemical composition and antimicrobial activity of volatile oils of three species of Leptospermum (Myrtaceae) grown in Brazil.
Herbicidal activity of Peumus boldus and Drimys winterii essential oils from Chile.
Antioxidant activity and chemical composition of essential oil from Atriplex undulata.
Cardiodepressive effect elicited by the essential oil of Alpinia speciosa is related to L-type Ca²+ current blockade.
Chemical investigation of the essential oil of Thymus linearis (Benth. ex Benth) from western Himalaya, India.
Activity of Melaleuca alternifolia (tea tree) oil on Influenza virus A/PR/8: study on the mechanism of action.
Evaluation of tea tree oil quality and ascaridole: a deep study by means of chiral and multi heart-cuts multidimensional gas chromatography system coupled to mass spectrometry detection.
Inhibitory effect of the essential oil from Chamaecyparis obtusa on the growth of food-borne pathogens.
Chemical diversity in the genus Alpinia (Zingiberaceae): comparative composition of four Alpinia species grown in Northern India.
Plasma-enhanced synthesis of bioactive polymeric coatings from monoterpene alcohols: a combined experimental and theoretical study.
Tea tree oil might combat melanoma.
Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.
Comparative analysis of essential oils of six Anthemis taxa from Serbia and Montenegro.
Acetylcholinesterase and butyrylcholinesterase inhibitory activity of Pinus species essential oils and their constituents.
Chemical composition and antimicrobial activity of the essential oils from New Caledonian Citrus macroptera and Citrus hystrix.
Compositional variability in essential oil from different parts of Alpinia speciosa from India.
Variation in volatile leaf oils of twelve eucalyptus species harvested from Hajeb Layoun arboreta (Tunisia).
Chemotypes of Pistacia atlantica leaf essential oils from Algeria.
Seasonal variation in the essential oil composition of Origanum majorana L. cultivated in Egypt.
Total phenolic content, radical scavenging properties, and essential oil composition of Origanum species from different populations.
Repellency of essential oils of Cryptomeria japonica (Pinaceae) against adults of the mosquitoes Aedes aegypti and Aedes albopictus (Diptera:Culicidae).
In vitro antiviral activity of Melaleuca alternifolia essential oil.
The effects of excipients for topical preparations on the human skin permeability of terpinen-4-ol contained in Tea tree oil: infrared spectroscopic investigations.
Supercritical fluid extraction of the volatile oil from Santolina chamaecyparissus.
Induction of necrosis and cell cycle arrest in murine cancer cell lines by Melaleuca alternifolia (tea tree) oil and terpinen-4-ol.
Host plant volatiles serve to increase the response of male European grape berry moths, Eupoecilia ambiguella, to their sex pheromone.
Comparative study on the antiviral activity of selected monoterpenes derived from essential oils.
Flower and root oils of the tunisian Daucus carota L. ssp. maritimus (Apiaceae): integrated analyses by GC, GC/MS, and 13C-NMR spectroscopy, and in vitro antibacterial activity.
Composition and biological activity of essential oil of Achillea ligustica All. (Asteraceae) naturalized in central Italy: ideal candidate for anti-cariogenic formulations.
Formulation study of tea tree oil patches.
Effects of the essential oil from leaves of Alpinia zerumbet on behavioral alterations in mice.
Antifungal and insecticidal activity of two Juniperus essential oils.
Acetylcholinesterase inhibitory activity and chemical composition of commercial essential oils.
Evaluation of the anticonvulsant activity of terpinen-4-ol.
Ovicidal and adulticidal activities of Origanum majorana essential oil constituents against insecticide-susceptible and pyrethroid/malathion-resistant Pediculus humanus capitis (Anoplura: Pediculidae).
Oriented responses of grapevine moth larvae Lobesia botrana to volatiles from host plants and an artificial diet on a locomotion compensator.
Composition and seasonal variation of essential oil in Alpinia zerumbet from Okinawa Island.
Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica.
Variability of the needle essential oils of Pinus peuce from different populations in Montenegro and Serbia.
Fragrance material review on 4-carvomenthenol.
Comparison of sugar, acids, and volatile composition in raspberry bushy dwarf virus-resistant transgenic raspberries and the wild type 'meeker' (rubus idaeus L.).
Free and hydrolytically released volatile compounds of Vitis vinifera L. cv. Fiano grapes as odour-active constituents of Fiano wine.
Volatile composition in raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry.
Toxicity of plant essential oils and their components against Lycoriella ingenua (Diptera: Sciaridae).
Comparison of the cidal activity of tea tree oil and terpinen-4-ol against clinical bacterial skin isolates and human fibroblast cells.
Commentary to the article "Human skin penetration of the major components of Australian tea tree oil applied in its pure form and as a 20% solution in vitro".
Role of the MexAB-OprM efflux pump of Pseudomonas aeruginosa in tolerance to tea tree (Melaleuca alternifolia) oil and its monoterpene components terpinen-4-ol, 1,8-cineole, and alpha-terpineol.
Chemical composition and antibacterial activity of essential oil from Artemisia feddei.
25 years of natural product R&D with New South Wales agriculture.
Comparative study of aromatic compounds in young red wines from cabernet sauvignon, cabernet franc, and cabernet gernischet varieties in China.
Human skin penetration of the major components of Australian tea tree oil applied in its pure form and as a 20% solution in vitro.
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).
Characterization of the volatile constituents in the essential oil of Pistacia lentiscus L. from different origins and its antifungal and antioxidant activity.
In vitro antifungal activity of the tea tree (Melaleuca alternifolia) essential oil and its major components against plant pathogens.
Response accuracy and odor sampling time in mice trained to discriminate between enantiomers of carvone and those of terpinen-4-ol.
Inhibitory effects of monoterpenes on seed germination and seedling growth.
A comparative evaluation of Origanum onites essential oil and its four major components as larvicides against the pine processionary moth, Thaumetopoea wilkinsoni Tams.
Analysis of aromatic and terpenic constituents of pepper extracts by capillary electrochromatography.
The effect of tea tree oil and antifungal agents on a reporter for yeast cell integrity signalling.
Gas chromatographic/mass spectrometric analysis of the essential oil of Houttuynia cordata Thunb by using on-column methylation with tetramethylammonium acetate.
Chemical composition and antimicrobial activity of the essential oil of Cryptomeria japonica.
Gas-chromatographic method for quantifying carvacrol, thymol, terpinen-4-ol, transl anethole, eugenol and trans-cinnamaldehyde in media simulating pig gut conditions.
Anticonflict effects of lavender oil and identification of its active constituents.
In vivo activity of terpinen-4-ol, the main bioactive component of Melaleuca alternifolia Cheel (tea tree) oil against azole-susceptible and -resistant human pathogenic Candida species.
Melaleuca alternifolia essential oil possesses potent anti-staphylococcal activity extended to strains resistant to antibiotics.
Discrimination between the enantiomers of carvone and of terpinen-4-ol odorants in normal rats and those with lesions of the olfactory bulbs.
Growth-inhibiting activity of active component isolated from Terminalia chebula fruits against intestinal bacteria.
Memory-enhancing effect of a supercritical carbon dioxide fluid extract of the needles of Abies koreana on scopolamine-induced amnesia in mice.
In vitro studies on release and human skin permeation of Australian tea tree oil (TTO) from topical formulations.
Susceptibility of pseudomonads to Melaleuca alternifolia (tea tree) oil and components.
Lethality of essential oil constituents towards the human louse, Pediculus humanus, and its eggs.
Lipolytic effects of citrus peel oils and their components.
Aqueous solubility of liquid monoterpenes at 293 K and relationship with calculated log P value.
Stratum corneum absorption and retention of linalool and terpinen-4-ol applied as gel or oily solution in humans.
Skin penetration of terpenes from essential oils and topical vehicles.
Supercritical carbon dioxide extraction of compounds with antimicrobial activity from Origanum vulgare L.: determination of optimal extraction parameters.
The essential oil constituents and antimicrobial activity of Anthemis aciphylla BOISS. var. discoidea BOISS.
Essential oil of the Persian sage, Salvia rhytidea Benth.
How does the type of vehicle influence the in vitro skin absorption and elimination kinetics of terpenes?
Topical use of tea tree oil reduces the dermal absorption of benzoic acid and methiocarb.
Effect of physicochemical properties of cyclic terpenes on their ex vivo skin absorption and elimination kinetics.
Chemical composition and anti-inflammatory activity of the volatile fractions from the bark of eight Mexican Bursera species.
A validated HPTLC method for determination of tea tree oil from cosmeceutical formulations.
Analysis of volatile components from Ziziphora taurica subsp. taurica by steam distillation, superheated-water extraction, and direct thermal desorption with GCxGC-TOFMS.
Terpinen-4-ol: mechanisms of relaxation on rabbit duodenum.
[Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation].
Enhancement of attraction and trap catches of the old-house borer, Hylotrupes bajulus (Coleoptera: Cerambycidae), by combination of male sex pheromone and monoterpenes.
Characteristic odor components of kumquat (Fortunella japonica Swingle) peel oil.
Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species.
Isolation and partial characterisation of a putative monoterpene synthase from Melaleuca alternifolia.
Application of multidimensional gas chromatography to the enantioselective characterisation of the essential oil of Eupatorium buniifolium Hooker et Arnott.
Tea tree oil concentration in follicular casts after topical delivery: determination by high-performance thin layer chromatography using a perfused bovine udder model.
Regulation of wheal and flare by tea tree oil: complementary human and rodent studies.
Tolerance of Pseudomonas aeruginosa to Melaleuca alternifolia (tea tree) oil is associated with the outer membrane and energy-dependent cellular processes.
Superheated water extraction, steam distillation and Soxhlet extraction of essential oils of Origanum onites.
Acaricidal activity of Melaleuca alternifolia (tea tree) oil: in vitro sensitivity of sarcoptes scabiei var hominis to terpinen-4-ol.
Composition and seasonal variation of the essential oils from two mandarin cultivars of southern Brazil.
Effect of storage on the essential oil composition of Piper nigrum L. fruits of different ripening states.
Inhibition of acetylcholinesterase by Tea Tree oil.
Aromatic components of the leaves of the New Zealand lemonwood tree Pittosporum eugenioides.
Terpinen-4-ol, the main component of Melaleuca alternifolia (tea tree) oil inhibits the in vitro growth of human melanoma cells.
Chemical and biological evaluation of the essential oils of different Melaleuca species.
Effect of the volatile constituents isolated from Thymus albicans, Th. mastichina, Th. carnosus and Thymbra capitata in sunflower oil.
Effects of monoterpenoids, acting alone or in pairs, on seed germination and subsequent seedling growth.
Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil.
Enantiomeric distribution of chiral compounds in orange juices according to their geographical origins.
Preferred age for assessment of qualitative and quantitative characteristics of the essential oil of tea tree (Melaleuca alternifolia) seedlings prior to plantation establishment.
Antihypertensive effects of the essential oil of Alpinia zerumbet and its main constituent, terpinen-4-ol, in DOCA-salt hypertensive conscious rats.
Characterization of volatiles in bullock's heart (Annona reticulata L.) fruit cultivars from Cuba.
Electroantennogram responses of Douglas-fir seed chalcids to plant volatiles.
Chemical composition and antifungal properties of essential oils of three Pistacia species.
Monoterpenoid accumulation in 1,8-cineole, terpinolene and terpinen-4-ol chemotypes of Melaleuca alternifolia seedlings.
Use of the enantiomeric composition for the assessment of the authenticity of fruit beverages.
Genetic control of monoterpene composition in the essential oil of Melaleuca alternifolia (Cheel).
[Chemical constituents in volatile oil from fruits of Alpinia oxyphylla Miq].
Cardiovascular effects of the essential oil of Alpinia zerumbet leaves and its main constituent, Terpinen-4-ol, in rats: role of the autonomic nervous system.
Compositions and the in vitro antimicrobial activities of the essential oils of Achillea setacea and Achillea teretifolia (Compositae).
Determination of monoterpene hydrocarbons and alcohols in Majorana hortensis Moench by micellar electrokinetic capillary chromatographic.
Tea tree oil reduces histamine-induced oedema in murine ears.
Tea tree oil reduces the swelling associated with the efferent phase of a contact hypersensitivity response.
Mechanism of action of Melaleuca alternifolia (tea tree) oil on Staphylococcus aureus determined by time-kill, lysis, leakage, and salt tolerance assays and electron microscopy.
Monoterpenoid accumulation in Melaleuca alternifolia seedlings.
Volatile oil comparison of cotyledon leaves of chemotypes of Melaleuca alternifolia.
Monoterpenic and norisoprenoidic glycoconjugates of Vitis vinifera L. cv. Melon B. as precursors of odorants in Muscadet wines.
Perceptual correlates of neural representations evoked by odorant enantiomers.
Essential oil composition of sea fennel (Crithmum maritimum) form Turkey.
Biotransformation of (R)- and (S)-terpinen-4-ol by the larvae of common cutworm (Spodoptera litura).
Composition and antimicrobial activity of the essential oils of two Origanum species.
Interactions between components of the essential oil of Melaleuca alternifolia.
Seasonal variation in chemical constituents of Santolina rosmarinifolia L. ssp. rosmarinifolia.
The water-soluble components of the essential oil of Melaleuca alternifolia (tea tree oil) suppress the production of superoxide by human monocytes, but not neutrophils, activated in vitro.
Comparison of eucalyptus camaldulensis Dehn. oils from Mozambique as obtained by hydrodistillation and supercritical carbon dioxide extraction.
Multidimensional Capillary GC-GC for the Analysis of Real Complex Samples. 3. Enantiomeric Distribution of Monoterpene Hydrocarbons and Monoterpene Alcohols of Mandarin Oils.
Terpinen-4-ol, the main component of the essential oil of Melaleuca alternifolia (tea tree oil), suppresses inflammatory mediator production by activated human monocytes.
Volatile oil variability in Thymus serpylloides ssp. gadorensis growing wild in Southeastern Spain.
Comparison of oil recovered from tea tree leaf by ethanol extraction and steam distillation.
In vitro effect of essential oils and isolated mono- and sesquiterpenes on Leishmania major and Trypanosoma brucei.
Isolation of the antiulcer compound in essential oil from the leaves of Cryptomeria japonica.
Comparison of headspace techniques for sampling volatile natural products in a dynamic system.
Chemotaxonomic study on Thymus villosus from Portugal.
Natural variation in the essential oil content of Melaleuca alternifolia Cheel (Myrtaceae).
Ethnobotany, volatile oils and secretion tissues of werneria poposa from Argentina.
Enhancement of Skin Penetration of Nonsteroidal Anti-Inflammatory Drugs from Extemporaneously Compounded Topical-Gel Formulations.
Biological activity of Melaleuca alternifola (Tea Tree) oil component, terpinen-4-ol, in human myelocytic cell line HL-60.
Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L.
Influence of drug lipophilicity on terpenes as transdermal penetration enhancers.
The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests.
Clonal production of tea tree oil high in terpinen-4-ol for use in formulations for the treatment of thrush.
Insecticidal activity of monoterpenoids to western corn rootworm (Coleoptera: Chrysomelidae), twospotted spider mite (Acari: Tetranychidae), and house fly (Diptera: Muscidae).
Terpene-enhanced transdermal permeation of water and ethanol in human epidermis.
Topical antiinflammatory activity of the major lipophilic constituents of the rhizome of Zingiber cassumunar. Part I: The essential oil.
[GC-MS analysis of essential oils from pericarps of Illicium brevistylum A. C. Smith and I. jiadifengpi B.N. Chang].
Antimicrobial effects of tea-tree oil and its major components on Staphylococcus aureus, Staph. epidermidis and Propionibacterium acnes.
Metabolism of 1,8-cineole in tea tree (Melaleuca alternifolia andM. linariifolia) by pyrgo beetle (Paropsisterna tigrina).
Antimicrobial activity of the major components of the essential oil of Melaleuca alternifolia.
Melaleuca oil (tea tree oil) dermatitis.
[Analysis of chemical constituents of essential oil from dechengqi decoction].
Study of the Essential Oil from Juniperus communis "Berries" (Cones) Growing Wild in Greece.
Antibacterial properties of the Vietnamese cajeput oil and ocimum oil in combination with antibacterial agents.
Electroantennogram responses of the southern pine beetle parasitoidDinotiscus dendroctoni (Ashmead) (Hymenoptera: Pteromalidae) to potential semiochemicals.
Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae).
The antimicrobial activity of the essential oil from Achillea fragrantissima.
Purification and characterization of the monoterpene cyclase gamma-terpinene synthase from Thymus vulgaris.
Fumigant toxicity of essential oils against four major stored-product insects.
Olfactory sensitivity of two sympatric species of rice leaf folders (Lepidoptera: Pyralidae) to plant volatiles.
Volatiles released from individual spruce bark beetle entrance holes Quantitative variations during the first week of attack.
The Leaf Oil of Liquidambar styraciflua.
The role of mass spectrometry in medicinal plant research.
Acetoxychavicol Acetate, an Antifungal Component of Alpinia galanga1.
Isolation and identification of mosquito repellents inArtemisia vulgaris.
[The quantitative composition of natural and technologically changed aromas of plants. II. Aroma compounds in oranges and their changes during juice processing (author's transl)].
Effect of various essential oils isolated from Douglas fir needles upon sheep and deer rumen microbial activity.
Publications by J-Stage
Cleavage of a-Dicarbonyl Compounds by Terpene Hydroperoxide

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C17073
HMDB (The Human Metabolome Database):HMDB35833
FooDB:FDB014601
YMDB (Yeast Metabolome Database):YMDB01790
Export Tariff Code:2906.19.5000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
FAO:4-Carvomenthenol

General Material Information

Preferred name 4-carvomenthenol
Trivial Name Terpinen-4-ol
Short Description 4-terpinenol
Formula C10 H18 O
Category Pure Compounds , Pure Compounds > Alcohols
CAS Number 562-74-3
Deleted CAS Number 1336-05-6
FEMA Number 2248
Flavis Number 2.072
ECHA Number 209-235-5
FDA UNII L65MV77ZG6
Nikkaji Number J6.503J
Beilstein Number 1906603
MDL MFCD00001562
COE Number 2229
xLogP3-AA 2.20 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 439 4-carvomenthenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 562-74-3 ; 4-CARVOMENTHENOL
Synonyms
  • 4-carvomenthenol (natural)
  • 4-carvomenthenol natural
  • 3-cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-
  • (±)-p- menth-1-en-4-ol
  • (±)-para- menth-1-en-4-ol
  • p- menth-1-en-4-ol
  • para- menth-1-en-4-ol
  • 1-p- menthen-4-ol
  • 1-para- menthen-4-ol
  • 1-menthene-4-ol
  • 4-methyl-1-(1-methyl ethyl)-3-cyclohexen-1-ol
  • 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol
  • 4-methyl-1-(1-methylethyl)-3-cyclohexene-1-ol
  • 4-methyl-1-[1-methylethyl]-3-cyclohexen-1-ol
  • 4-methyl-1-isopropyl-3-cyclohexen-1-ol
  • 4-methyl-1-propan-2-ylcyclohex-3-en-1-ol
  • 1-methyl-4-isopropyl-1-cyclohexen-4-ol
  • 1-(1-methylethyl)-4-methyl-3-cyclohexen-1-ol
  • origanol
  • (±)-1-iso propyl-4-methyl-3-cyclohexen-1-ol
  • 1-iso propyl-4-methylcyclohex-3-en-1-ol
  • (1)-1-(iso propyl)-4-methyl cyclohex-3-en-1-ol
  • (1)-1-(iso propyl)-4-methylcyclohex-3-en-1-ol
  • tea tree heart
  • terpinen-4-ol
  • (±)- terpinen-4-ol
  • 1-terpinen-4-ol
  • terpinen-4-ol natural
  • terpinene 1-ol-4
  • terpinene-4-ol
  • terpinene-4-ol (ex eucalyptus)
  • terpinene-4-ol natural
  • 4-terpinenol
  • 4-terpinenol natural
  • D- terpinenol natural
  • terpinenol-4
  • terpinenol-4 natural
  • DL- terpinenol, synthetic
  • terpinenol4 natural isolate
  • (±)-4-terpineol
  • 4-terpineol
  • DL-4-terpineol
  • 4-methyl-1-propan-2-ylcyclohex-3-en-1-ol
  • 3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-
  • p-Menth-1-en-4-ol
  • 4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol
  • 1-Terpinen-4-ol
  • 4-Terpinenol
  • 4-Terpineol
  • Terpineol-4
  • 4-Methyl-1-isopropyl-3-cyclohexen-1-ol
  • 1-(1-Methylethyl)-4-methyl-3-cyclohexen-1-ol
  • dl-4-Terpineol
  • (±)-4-Terpineol
  • (±)-Terpinen-4-ol
  • Melaleucol
  • NSC 147749
  • Terpin-4-ol
  • 1-Isopropyl-4-methylcyclohex-3-en-1-ol
  • 4-Methyl-1-(1-methylethyl)-3-cyclohexene-1-ol
  • 1-Terpen-4-ol

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 154.2526550293
Specific gravity @ 25 °C
Pounds per Gallon 7.722 to 7.772
Refractive Index 1.476 to 1.48 @ 20 °C
Boiling Point 88 to 90°C @ 6 mm Hg
Vapor Pressure 0.048 mmHg @ 25 °C
Flash Point TCC Value 79.44 °C TCC
logP (o/w) 3.26
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
water, 386.6 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Spicy
peppery, woody, earthy, musty, sweet, mentholic, citrus, terpenic, spicy
Odor strength medium
Substantivity 20 hour(s) at 100.00 %
Luebke, William tgsc, (1992) At 100.00 %. pepper woody earth musty sweet
Mosciano, Gerard P&F 23, No. 4, 33, (1998) At 5.00 %. Woody, ceding, mentholic, citrus terpy, spicy
Flavor Type: Cooling
cooling, mentholic, woody, weedy, earthy, herbal, spicy, citrus, clove
Luebke, William tgsc, (1992) Cooling mentholic woody weedy earthy herbal spicy citrus
Mosciano, Gerard P&F 23, No. 4, 33, (1998) At 25.00 ppm. Cooling, woody, earthy, clove spicy with a citrus undernote
General comment Sweet citrus green tropical fruity
Useful in: mint, savory vegetable, savory spices, fruity citrus, fruity red, fruity yellow, fruity tropical, sweet others, alcoholics. Earthy, musty, terpenic, lime, thyme

Occurrences

Applications

Applications flavor and fragrance agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Human Experience:
5 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 1300 mg/kg
(Moreno, 1977v)

oral-mouse LD50 1016 mg/kg
Zhonghua Jiehe He Huxixi Jibing Zazhi. Chinese Journal of Tuberculosis and Respiratory Diseases. Vol. 4(4), Pg.203,1981.

intraperitoneal-mouse LD50 250 mg/kg
KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Cesko-Slovenska Farmacie. Vol. 8, Pg. 433, 1959.

intramuscular-mouse LD50 780 mg/kg
KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Cesko-Slovenska Farmacie. Vol. 8, Pg. 433, 1959.

intramuscular-rat LD50 1500 mg/kg
KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Cesko-Slovenska Farmacie. Vol. 8, Pg. 433, 1959.

Dermal Toxicity:
skin-rabbit LD50 > 2500 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 833, 1982

subcutaneous-mouse LD50 750 mg/kg
KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Cesko-Slovenska Farmacie. Vol. 8, Pg. 433, 1959.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
maximum skin levels for fine fragrances:
0.1300 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2006)
Recommendation for 4-carvomenthenol usage levels up to:
5.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
0.0430 %
Dermal Systemic Exposure in Cosmetic Products:
0.0011 mg/kg/day (IFRA, 2006)
Maximised Survey-derived Daily Intakes (MSDI-EU): 150.00 (μg/capita/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -7.00000
beverages(nonalcoholic): 1.0000021.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 1.0000084.00000
fruit ices: 1.0000084.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 7.0000063.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 18 (FGE.18): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical group 6
View page or View pdf

Flavouring Group Evaluation 18, Revision 1 (FGE. 18 Rev1)[1] : Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):562-74-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11230
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
4-methyl-1-propan-2-ylcyclohex-3-en-1-ol
Chemidplus:0000562743
RTECS:OT0175110 for cas# 562-74-3
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