Details
Stereochemistry | RACEMIC |
Molecular Formula | C10H18O |
Molecular Weight | 154.2493 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C1(O)CCC(C)=CC1
InChI
InChIKey=WRYLYDPHFGVWKC-UHFFFAOYSA-N
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3
4-Carvomenthenol (Terpinen-4-ol) is an anti-inflammatory and antimicrobial agent. 4-Carvomenthenol is a fragrance ingredient used in decorative
cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents. Its use worldwide is in the region of 1–10
metric tonnes per annum.
The maximum skin level that results from the use of
4-carvementhenol in formulae that go into fine fragrances has
been reported to be 0.13%. 4-Carvomenthenol has been shown to have antiviral, antibacterial, antifungal, and insecticidal effects as well as antioxidant and anti-inflammatory activities. It is a putative anitcancer agent. 4-carvementhenol exerts its antitumor effects by triggering caspase-dependent apoptosis in human melanoma cells or by inducing necrotic cell death and cell-cycle arrest in mouse mesothelioma and melanomacell lines without affecting normal cells. Caspase-dependent mitochondrial dysfunction is the mechanism of terpinen-4-ol-induced apoptosis in nonsmall lung cancer cells. Down-regulation of Bcl-2, XIAP and survivin suggests that ter-pinen-4-ol increases the susceptibility of NSCLC cells toapoptosis induction. Notably, the ability of terpinen-4-ol to induce apoptosis in NSCLC cells is p53-dependent. It has also been shown that the growth of s.c. xenograft tumors was remarkably inhibited by intratumoral injection of terpinen-4-ol, indicating that the agent also has potential for clinical anticancer activity.
Approval Year
PubMed
Title | Date | PubMed |
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25 years of natural product R&D with New South Wales agriculture. | 2005 Oct 31 |
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Gas-chromatographic method for quantifying carvacrol, thymol, terpinen-4-ol, transl anethole, eugenol and trans-cinnamaldehyde in media simulating pig gut conditions. | 2006 |
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Aqueous solubility of liquid monoterpenes at 293 K and relationship with calculated log P value. | 2006 Apr |
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Memory-enhancing effect of a supercritical carbon dioxide fluid extract of the needles of Abies koreana on scopolamine-induced amnesia in mice. | 2006 Aug |
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Susceptibility of pseudomonads to Melaleuca alternifolia (tea tree) oil and components. | 2006 Aug |
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Anticonflict effects of lavender oil and identification of its active constituents. | 2006 Dec |
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Melaleuca alternifolia essential oil possesses potent anti-staphylococcal activity extended to strains resistant to antibiotics. | 2006 Jul-Sep |
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Stratum corneum absorption and retention of linalool and terpinen-4-ol applied as gel or oily solution in humans. | 2006 Jun |
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Skin penetration of terpenes from essential oils and topical vehicles. | 2006 Mar |
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Lipolytic effects of citrus peel oils and their components. | 2006 May 3 |
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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. | 2006 Nov 3 |
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In vitro studies on release and human skin permeation of Australian tea tree oil (TTO) from topical formulations. | 2006 Oct |
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Growth-inhibiting activity of active component isolated from Terminalia chebula fruits against intestinal bacteria. | 2006 Sep |
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Discrimination between the enantiomers of carvone and of terpinen-4-ol odorants in normal rats and those with lesions of the olfactory bulbs. | 2006 Sep 27 |
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The effect of tea tree oil and antifungal agents on a reporter for yeast cell integrity signalling. | 2007 Apr |
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A comparative evaluation of Origanum onites essential oil and its four major components as larvicides against the pine processionary moth, Thaumetopoea wilkinsoni Tams. | 2007 Aug |
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Characterization of the volatile constituents in the essential oil of Pistacia lentiscus L. from different origins and its antifungal and antioxidant activity. | 2007 Aug 22 |
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Ethnoveterinary medicines used for ruminants in British Columbia, Canada. | 2007 Feb 26 |
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Screening of antibacterial activities of twenty-one oxygenated monoterpenes. | 2007 Jul-Aug |
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In vitro antifungal activity of the tea tree (Melaleuca alternifolia) essential oil and its major components against plant pathogens. | 2007 Jun |
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Analysis of aromatic and terpenic constituents of pepper extracts by capillary electrochromatography. | 2007 Mar |
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Chemical composition and antimicrobial activity of the essential oil of Cryptomeria japonica. | 2007 Mar |
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Inhibitory effects of monoterpenes on seed germination and seedling growth. | 2007 Mar-Apr |
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Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae). | 2007 Sep |
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Response accuracy and odor sampling time in mice trained to discriminate between enantiomers of carvone and those of terpinen-4-ol. | 2007 Sep |
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Percutaneous permeation enhancement by terpenes: mechanistic view. | 2008 |
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Comparison of the cidal activity of tea tree oil and terpinen-4-ol against clinical bacterial skin isolates and human fibroblast cells. | 2008 Apr |
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Comparison of sugar, acids, and volatile composition in raspberry bushy dwarf virus-resistant transgenic raspberries and the wild type 'meeker' (rubus idaeus L.). | 2008 Aug 13 |
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Toxicity of plant essential oils and their components against Lycoriella ingenua (Diptera: Sciaridae). | 2008 Feb |
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Chemical composition, antimicrobial and antioxidant activities of the essential oil of Tibetan herbal medicine Dracocephalum heterophyllum Benth. | 2008 Jan 10 |
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Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica. | 2008 Jul |
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Free and hydrolytically released volatile compounds of Vitis vinifera L. cv. Fiano grapes as odour-active constituents of Fiano wine. | 2008 Jul 21 |
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Volatile composition in raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry. | 2008 Jun 11 |
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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". | 2008 Mar |
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Human skin penetration of the major components of Australian tea tree oil applied in its pure form and as a 20% solution in vitro. | 2008 May |
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Fragrance material review on 4-carvomenthenol. | 2008 Nov |
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Oriented responses of grapevine moth larvae Lobesia botrana to volatiles from host plants and an artificial diet on a locomotion compensator. | 2009 Apr |
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Composition and seasonal variation of essential oil in Alpinia zerumbet from Okinawa Island. | 2009 Apr |
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In vitro antiviral activity of Melaleuca alternifolia essential oil. | 2009 Dec |
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Formulation study of tea tree oil patches. | 2009 Jan |
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Effects of the essential oil from leaves of Alpinia zerumbet on behavioral alterations in mice. | 2009 Jan |
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Antifungal and insecticidal activity of two Juniperus essential oils. | 2009 Jan |
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Evaluation of the anticonvulsant activity of terpinen-4-ol. | 2009 Jan-Feb |
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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. | 2009 Jun |
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Acetylcholinesterase inhibitory activity and chemical composition of commercial essential oils. | 2009 May 27 |
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Supercritical fluid extraction of the volatile oil from Santolina chamaecyparissus. | 2009 Sep |
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Composition and biological activity of essential oil of Achillea ligustica All. (Asteraceae) naturalized in central Italy: ideal candidate for anti-cariogenic formulations. | 2009 Sep |
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Induction of necrosis and cell cycle arrest in murine cancer cell lines by Melaleuca alternifolia (tea tree) oil and terpinen-4-ol. | 2010 Apr |
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Comparative study on the antiviral activity of selected monoterpenes derived from essential oils. | 2010 May |
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The effects of excipients for topical preparations on the human skin permeability of terpinen-4-ol contained in Tea tree oil: infrared spectroscopic investigations. | 2010 Sep-Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18640221
The acute oral toxicity of 4-carvomenthenol was determined in 10/rats/group. 4-Carvomenthenol was administered at
dose levels: 0.6, 1.22, 2.47, and 5.0 g/kg. The animals were observed
for 14 days. The acute oral toxicity was determined to be 1.3 g/kg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21760828
To determine the cytotoxic effect of terpinen-4-ol on cell, A549 and CL1-0 cells were treated with 0.02% to 0.1% terpinen-4-ol for 24 hours, and cell viability was determined using the MTT assay. At 24 hours, the estimated IC50 values were 0.052% in A549 cells and 0.046% in CL1-0 cells, respectively.
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CFR |
21 CFR 172.515
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JECFA EVALUATION |
4-CARVOMENTHENOL
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TERPINEN-4-OL
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SUBSTANCE RECORD