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
Molecular Formula | C10H18O |
Molecular Weight | 154.2493 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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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Chemical composition and antifungal properties of essential oils of three Pistacia species. | 2003 Feb |
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Antihypertensive effects of the essential oil of Alpinia zerumbet and its main constituent, terpinen-4-ol, in DOCA-salt hypertensive conscious rats. | 2003 Jun |
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Effects of monoterpenoids, acting alone or in pairs, on seed germination and subsequent seedling growth. | 2003 Oct |
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Isolation and partial characterisation of a putative monoterpene synthase from Melaleuca alternifolia. | 2004 Dec |
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Terpinen-4-ol, the main component of Melaleuca alternifolia (tea tree) oil inhibits the in vitro growth of human melanoma cells. | 2004 Feb |
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Aromatic components of the leaves of the New Zealand lemonwood tree Pittosporum eugenioides. | 2004 Jan-Feb |
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Inhibition of acetylcholinesterase by Tea Tree oil. | 2004 Mar |
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Acaricidal activity of Melaleuca alternifolia (tea tree) oil: in vitro sensitivity of sarcoptes scabiei var hominis to terpinen-4-ol. | 2004 May |
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Composition and seasonal variation of the essential oils from two mandarin cultivars of southern Brazil. | 2004 May 19 |
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[Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation]. | 2004 Nov |
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Application of multidimensional gas chromatography to the enantioselective characterisation of the essential oil of Eupatorium buniifolium Hooker et Arnott. | 2005 Jan-Feb |
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A validated HPTLC method for determination of tea tree oil from cosmeceutical formulations. | 2005 Jun 1 |
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Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species. | 2005 Mar 9 |
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25 years of natural product R&D with New South Wales agriculture. | 2005 Oct 31 |
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Chemical composition and anti-inflammatory activity of the volatile fractions from the bark of eight Mexican Bursera species. | 2005 Sep |
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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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Supercritical carbon dioxide extraction of compounds with antimicrobial activity from Origanum vulgare L.: determination of optimal extraction parameters. | 2006 Feb |
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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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Skin penetration of terpenes from essential oils and topical vehicles. | 2006 Mar |
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Topical use of tea tree oil reduces the dermal absorption of benzoic acid and methiocarb. | 2006 Mar |
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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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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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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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Chemical composition and antibacterial activity of essential oil from Artemisia feddei. | 2007 Dec |
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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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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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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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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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In vitro antiviral activity of Melaleuca alternifolia essential oil. | 2009 Dec |
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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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:52:54 GMT 2023
by
admin
on
Fri Dec 15 16:52:54 GMT 2023
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Record UNII |
L65MV77ZG6
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 172.515
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JECFA EVALUATION |
4-CARVOMENTHENOL
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