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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
Structure of 4-TERPINEOL, (±)-

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
25 years of natural product R&D with New South Wales agriculture.
2005 Oct 31
Gas-chromatographic method for quantifying carvacrol, thymol, terpinen-4-ol, transl anethole, eugenol and trans-cinnamaldehyde in media simulating pig gut conditions.
2006
Memory-enhancing effect of a supercritical carbon dioxide fluid extract of the needles of Abies koreana on scopolamine-induced amnesia in mice.
2006 Aug
Susceptibility of pseudomonads to Melaleuca alternifolia (tea tree) oil and components.
2006 Aug
Anticonflict effects of lavender oil and identification of its active constituents.
2006 Dec
Melaleuca alternifolia essential oil possesses potent anti-staphylococcal activity extended to strains resistant to antibiotics.
2006 Jul-Sep
Stratum corneum absorption and retention of linalool and terpinen-4-ol applied as gel or oily solution in humans.
2006 Jun
Skin penetration of terpenes from essential oils and topical vehicles.
2006 Mar
Lipolytic effects of citrus peel oils and their components.
2006 May 3
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
In vitro studies on release and human skin permeation of Australian tea tree oil (TTO) from topical formulations.
2006 Oct
Growth-inhibiting activity of active component isolated from Terminalia chebula fruits against intestinal bacteria.
2006 Sep
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
The effect of tea tree oil and antifungal agents on a reporter for yeast cell integrity signalling.
2007 Apr
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
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
Chemical composition and antibacterial activity of essential oil from Artemisia feddei.
2007 Dec
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.
2007 Feb 26
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
2007 Jul-Aug
In vitro antifungal activity of the tea tree (Melaleuca alternifolia) essential oil and its major components against plant pathogens.
2007 Jun
Analysis of aromatic and terpenic constituents of pepper extracts by capillary electrochromatography.
2007 Mar
Chemical composition and antimicrobial activity of the essential oil of Cryptomeria japonica.
2007 Mar
Inhibitory effects of monoterpenes on seed germination and seedling growth.
2007 Mar-Apr
Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).
2007 Sep
Response accuracy and odor sampling time in mice trained to discriminate between enantiomers of carvone and those of terpinen-4-ol.
2007 Sep
Percutaneous permeation enhancement by terpenes: mechanistic view.
2008
Comparison of the cidal activity of tea tree oil and terpinen-4-ol against clinical bacterial skin isolates and human fibroblast cells.
2008 Apr
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
Toxicity of plant essential oils and their components against Lycoriella ingenua (Diptera: Sciaridae).
2008 Feb
Chemical composition, antimicrobial and antioxidant activities of the essential oil of Tibetan herbal medicine Dracocephalum heterophyllum Benth.
2008 Jan 10
Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica.
2008 Jul
Free and hydrolytically released volatile compounds of Vitis vinifera L. cv. Fiano grapes as odour-active constituents of Fiano wine.
2008 Jul 21
Volatile composition in raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry.
2008 Jun 11
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
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
Fragrance material review on 4-carvomenthenol.
2008 Nov
Oriented responses of grapevine moth larvae Lobesia botrana to volatiles from host plants and an artificial diet on a locomotion compensator.
2009 Apr
Composition and seasonal variation of essential oil in Alpinia zerumbet from Okinawa Island.
2009 Apr
In vitro antiviral activity of Melaleuca alternifolia essential oil.
2009 Dec
Formulation study of tea tree oil patches.
2009 Jan
Effects of the essential oil from leaves of Alpinia zerumbet on behavioral alterations in mice.
2009 Jan
Antifungal and insecticidal activity of two Juniperus essential oils.
2009 Jan
Evaluation of the anticonvulsant activity of terpinen-4-ol.
2009 Jan-Feb
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
Acetylcholinesterase inhibitory activity and chemical composition of commercial essential oils.
2009 May 27
Supercritical fluid extraction of the volatile oil from Santolina chamaecyparissus.
2009 Sep
Composition and biological activity of essential oil of Achillea ligustica All. (Asteraceae) naturalized in central Italy: ideal candidate for anti-cariogenic formulations.
2009 Sep
Induction of necrosis and cell cycle arrest in murine cancer cell lines by Melaleuca alternifolia (tea tree) oil and terpinen-4-ol.
2010 Apr
Comparative study on the antiviral activity of selected monoterpenes derived from essential oils.
2010 May
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

Patents

Sample Use Guides

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
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 Thu Jul 06 00:16:42 UTC 2023
Edited
by admin
on Thu Jul 06 00:16:42 UTC 2023
Record UNII
L65MV77ZG6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-TERPINEOL, (±)-
Common Name English
4-CARVOMENTHENOL
FHFI  
Preferred Name English
4-METHYL-1-(1-METHYLETHYL)-3-CYCLOHEXEN-1-OL
Systematic Name English
4-TERPINEOL [INCI]
Common Name English
4-TERPINEOL
INCI  
INCI  
Official Name English
(±)-4-TERPINEOL
Common Name English
4-CARVOMENTHENOL [FHFI]
Common Name English
TERPINEN-4-OL,(±)-
Common Name English
TERPINENOL-4
Common Name English
TERPINEN-4-OL
FCC  
Systematic Name English
4-METHYL-1-(PROPAN-2-YL)CYCLOHEX-3-EN-1-OL
Systematic Name English
3-CYCLOHEXEN-1-OL, 4-METHYL-1-(1-METHYLETHYL)-
Systematic Name English
(±)-TERPINEN-4-OL
Systematic Name English
DL-4-TERPINEOL
Common Name English
P-MENTH-1-EN-4-OL
Systematic Name English
MELALEUCOL
Common Name English
METHYL-1-(1-METHYLETHYL)-3-CYCLOHEXEN-1-OL
Systematic Name English
1-(ISOPROPYL)-4-METHYLCYCLOHEX-3-EN-1-OL
Systematic Name English
1-P-MENTHEN-4-OL
Common Name English
NSC-147749
Code English
FEMA NO. 2248
Code English
PARA-MENTH-1-EN-4-OL
Systematic Name English
TERPINEN-4-OL [FCC]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
JECFA EVALUATION 4-CARVOMENTHENOL
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
Code System Code Type Description
DRUG BANK
DB12816
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
PUBCHEM
11230
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
CHEBI
78884
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
SMS_ID
300000039469
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
WIKIPEDIA
TERPINEN-4-OL
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
FDA UNII
L65MV77ZG6
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
RXCUI
1314261
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID4044824
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
CAS
562-74-3
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
NSC
147749
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
DAILYMED
L65MV77ZG6
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
HSDB
8264
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
ECHA (EC/EINECS)
209-235-5
Created by admin on Thu Jul 06 00:16:42 UTC 2023 , Edited by admin on Thu Jul 06 00:16:42 UTC 2023
PRIMARY
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