Page last updated: 2024-12-05

terpinolene

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Terpinolene is a monocyclic monoterpene hydrocarbon found in many essential oils, including tea tree oil, pine oil, and citrus oils. It has a fresh, piney, citrusy aroma. Terpinolene is synthesized through the reaction of α-terpineol with acid, and it is also produced naturally by plants. Terpinolene has a variety of biological activities, including antifungal, antibacterial, and antioxidant properties. It is also a potential insecticide and larvicide. Terpinolene is studied for its potential health benefits, including its ability to improve cognitive function, reduce inflammation, and protect against cancer. Its ability to act as a flavoring agent is also being investigated. Terpinolene is a versatile compound with potential applications in a variety of fields.'

Cross-References

ID SourceID
PubMed CID11463
CHEMBL ID454697
CHEBI ID9457
MeSH IDM0088126

Synonyms (75)

Synonym
p-mentha-1,4(8)-diene
cyclohexene, 1-methyl-4-(1-methylethylidene)-
.gamma.-terpinolene
1-methyl-4-(1-methylethylidene)cyclohexene
1,4(8)-p-menthadiene
1-methyl-4-(propan-2-ylidene)cyclohexene
alpha-terpinolene
isoterpinene
CHEBI:9457 ,
terpinolen
4-isopropylidene-1-methylcyclohexene
1-methyl-4-(1-methylethylidene)-1-cyclohexene
1-methyl-4-isopropylidene-1-cyclohexene
hsdb 5702
einecs 209-578-0
p-menth-1,4(8)-diene
1,4(8)-terpadiene
fema number 3046
fema no. 3046
un2541
tereben
ai3-24378
nofmer tp
586-62-9
C06075
terpinolene ,
terpinolene, >=90%
1-methyl-4-propan-2-ylidenecyclohexene
BMSE000504
p-meth-1-en-8-yl-formate
cyclohexene, 3-methyl-6-(1-methylethylidene)- (9ci)
CHEMBL454697
T0817
LMPR0102090062
1-methyl-4-(propan-2-ylidene)cyclohexene p-mentha-1,4(8)-diene
tox21_303268
dtxcid507222
NCGC00256963-01
cas-586-62-9
dtxsid0027222 ,
terpinolene [un2541] [flammable liquid]
ec 209-578-0
unii-n9830x5ksl
n9830x5ksl ,
FT-0632449
terpinolene [hsdb]
terpinolene [fhfi]
1-methyl-4-(propan-2-ylidene)cyclohex-1-ene
4-isopropylidene-1-methyl-cyclohexene
Q-201793
.alpha.- terpinolen
un 2541
.alpha.-terpinolene
1-methyl-4-(1-methylethylidene)-1-cyclohexene #
mfcd00049191
AKOS028108377
terpinolene, technical, >=85% (gc)
terpinolene, purum, >=95.0% (gc)
terpinolene, analytical standard
terpinolene 1000 microg/ml in isopropanol
fema 3046
alpha -terpinolene
1-methyl-4-(1-methylethylidene)cyclohexene, 9ci
1-methyl-4-(1-methylethylidene)-cyclohexene
terpinolene with gc
Q2405051
EN300-125038
delta-terpinene
9LR ,
cyclohexene, 1-methyl-4-(1-methylethylidene)-, (r)-
4-isopropylidene-1-methylcyclohexane
d-1-methyl-4-isopropenyl-1-cyclohexene
Z1255360533
alpha-terpinolene 1000 microg/ml in isopropanol
FS-6812

Research Excerpts

Overview

Terpinolene is a cyclic monoterpene compound found in some Labiatae herbs. It is present in essential oils of many aromatic plant species.

ExcerptReferenceRelevance
"Terpinolene (TPO) is a natural monoterpene present in essential oils of many aromatic plant species. "( Anticancer and antioxidant properties of terpinolene in rat brain cells.
Aydin, E; Taşdemir, S; Türkez, H, 2013
)
2.1
"Terpinolene is a cyclic monoterpene compound found in some Labiatae herbs. "( The sedative effect of inhaled terpinolene in mice and its structure-activity relationships.
Ito, K; Ito, M, 2013
)
2.12

Bioavailability

ExcerptReferenceRelevance
" The bioavailability study of IND was performed in rats."( Effect of adhesive matrix composition and terpinolene on indomethacin bioavailability in rats from transdermal therapeutic system.
Cal, K; Janicki, S; Sznitowska, M, 2008
)
0.61

Dosage Studied

ExcerptRelevanceReference
" albopictus larvae and mortality was dosage dependent."( Larvicidal and repellent activity of Hyptis suaveolens (Lamiaceae) essential oil against the mosquito Aedes albopictus Skuse (Diptera: Culicidae).
Benelli, G; Canale, A; Ceccarini, L; Cioni, PL; Conti, B; Flamini, G; Macchia, M; Profeti, R, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
sedativeA central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
insect repellentAn insecticide that acts as a repellent to insects.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
volatile oil componentAny plant metabolite that is found naturally as a component of a volatile oil.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
p-menthadieneA monoterpene that consists of an unsaturated p-menthane skeleton having two double bonds.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (3)

PathwayProteinsCompounds
Monoterpenoid Biosynthesis618
monoterpene biosynthesis1913
Myrcene biosynthesis013

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
progesterone receptorHomo sapiens (human)Potency0.15360.000417.946075.1148AID1346784
pregnane X nuclear receptorHomo sapiens (human)Potency43.27710.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency68.58960.000229.305416,493.5996AID743079
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency61.65240.001024.504861.6448AID743215
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency24.33650.000323.4451159.6830AID743065
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID332912Antimicrobial activity Propionibacterium acnes ATCC 11827 after 2 days by broth dilution method1994Journal of natural products, Jan, Volume: 57, Issue:1
Naturally occurring antiacne agents.
AID1090744Antifungal activity against Aspergillus flavus assessed as mycelial growth at 60 uL after 4 to 12 days by agar disk diffusion method relative to untreated control2007Journal of agricultural and food chemistry, Aug-22, Volume: 55, Issue:17
Characterization of the volatile constituents in the essential oil of Pistacia lentiscus L. from different origins and its antifungal and antioxidant activity.
AID1090745Antifungal activity against Aspergillus flavus assessed as mycelial growth at 20 uL after 4 to 12 days by agar disk diffusion method relative to untreated control2007Journal of agricultural and food chemistry, Aug-22, Volume: 55, Issue:17
Characterization of the volatile constituents in the essential oil of Pistacia lentiscus L. from different origins and its antifungal and antioxidant activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (66)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (1.52)18.7374
1990's2 (3.03)18.2507
2000's17 (25.76)29.6817
2010's31 (46.97)24.3611
2020's15 (22.73)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 64.89

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index64.89 (24.57)
Research Supply Index4.28 (2.92)
Research Growth Index5.58 (4.65)
Search Engine Demand Index107.18 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (64.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.43%)5.53%
Reviews3 (4.29%)6.00%
Case Studies1 (1.43%)4.05%
Observational0 (0.00%)0.25%
Other65 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]