Compounds > alpha-terpinene
Page last updated: 2024-11-05

alpha-terpinene

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

Alpha-terpinene is a monoterpene found in many essential oils, particularly those derived from coniferous plants like pine and fir. It is a colorless liquid with a pleasant, citrus-like aroma. Its synthesis can occur through various methods, including the dehydration of terpineol, the isomerization of limonene, and the reaction of myrcene with an acid catalyst. Alpha-terpinene exhibits various biological effects, including antioxidant, antimicrobial, and anti-inflammatory properties. It is known to inhibit the growth of certain bacteria and fungi. Studies are conducted to explore its potential therapeutic applications, particularly in the treatment of skin infections and inflammatory conditions. Its importance lies in its potential for developing novel pharmaceutical and cosmetic products. Researchers continue to investigate its properties and mechanisms of action to better understand its potential benefits.'

Cross-References

ID SourceID
PubMed CID7462
CHEMBL ID2251642
CHEBI ID10334
MeSH IDM0313696

Synonyms (66)

Synonym
AKOS015841730
1-methyl-4-(1-methylethyl)-1,3-cyclohexadiene
p-mentha-1,3-diene
1-isopropyl-4-methyl-1,3-cyclohexadiene
terpilene
1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene
CHEBI:10334 ,
.alpha.-terpinen
fema no. 3558
alpha-terpinen
1,3-cyclohexadiene, 1-methyl-4-isopropyl-
ccris 9058
einecs 202-795-1
1-methyl-4-isopropylcyclohexadiene-1,3
ai3-26467
inchi=1/c10h16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8h,5,7h2,1-3h
1,3-cyclohexadiene, 1-methyl-4-(1-methylethyl)-
1-isopropyl-4-methylcyclohexa-1,3-diene
99-86-5
alpha-terpinene ,
C09898
alpha-terpinene, >=89%, fcc, fg
alpha-terpinene, 85%
alpha-terpinene, >=95.0% (gc)
LMPR0102090026
1-methyl-4-propan-2-ylcyclohexa-1,3-diene
M0317
NCGC00248299-01
dtxcid7021237
cas-99-86-5
tox21_301126
dtxsid9041237 ,
NCGC00255025-01
i24x278ap1 ,
unii-i24x278ap1
alphaterpinene
FT-0622940
EPITOPE ID:123897
CHEMBL2251642
p-mentha-1,3-diene [fhfi]
1-methyl-4-isopropyl-1,3-cyclohexadiene
4-isopropyl-1-methyl-1,3-cyclohexadiene
.alpha.-terpinene
.alpha.terpinene
alpha-terpinene [fcc]
1-isopropyl-4-methyl-cyclohexa-1,3-diene
W-100014
.alpha.-terpine
mfcd00001534
a-terpinene =89%, contains bht as stabilizer
alpha-terpinene, analytical standard
alpha -terpinene
fema 3558
a-terpinene
Q423851
E75753
alpha-terpinene alpha-terpinene
CS-0039183
alpha-terpinene 2000 microg/ml in acetonitrile
HY-W020182
9MI ,
BS-33443
-terpinen
alpha-terpinene (~90%)
Z1255364643
EN300-6738504

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"9 µg cm(-3) ) was the most toxic compound, followed by citronellyl acetate (16."( Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae.
Ahn, YJ; Choi, BR; Han, J; Kim, SI; Lee, SG, 2011)		0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
volatile oil componentAny plant metabolite that is found naturally as a component of a volatile oil.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (2)

ClassDescription
monoterpeneA C10 terpene.
cyclohexadiene
[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 (1)

PathwayProteinsCompounds
trichome monoterpenes biosynthesis210
trichome monoterpenes biosynthesis29

Protein Targets (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
estrogen nuclear receptor alphaHomo sapiens (human)Potency1.38010.000229.305416,493.5996AID743075
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (12)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
AID1111942Insecticidal activity against abamectin-resistant female Tetranychus urticae ART-53 (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay2011Pest management science, Dec, Volume: 67, Issue:12
Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae.
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.
AID1111945Insecticidal activity against chlorfenapyr-resistant female Tetranychus urticae CRT-53 (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay2011Pest management science, Dec, Volume: 67, Issue:12
Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae.
AID1111946Insecticidal activity against acaricide-susceptible female Tetranychus urticae KST (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay2011Pest management science, Dec, Volume: 67, Issue:12
Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae.
AID1111944Insecticidal activity against fenpropathrin-resistant female Tetranychus urticae FRT-53 (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay2011Pest management science, Dec, Volume: 67, Issue:12
Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae.
AID1111619Contact toxicity against adult Sitophilus zeamais assessed as mortality applied to dorsal thorax of insect measured daily for 1 week2011Pest management science, Jun, Volume: 67, Issue:6
Composition of essential oil of Chinese Chenopodium ambrosioides and insecticidal activity against maize weevil, Sitophilus zeamais.
AID1111943Insecticidal activity against pyridaben-resistant female Tetranychus urticae PRT-53 (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay2011Pest management science, Dec, Volume: 67, Issue:12
Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae.
AID1111620Insecticidal activity against adult Sitophilus zeamais assessed as mortality measured daily for 1 week by fumigation assay2011Pest management science, Jun, Volume: 67, Issue:6
Composition of essential oil of Chinese Chenopodium ambrosioides and insecticidal activity against maize weevil, Sitophilus zeamais.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's2 (40.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.77

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index45.77 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.99 (4.65)
Search Engine Demand Index62.09 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (45.77)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
menthol
Menthol: A monoterpene cyclohexanol produced from mint oils.		2.0610p-menthane monoterpenoid;
secondary alcohol		volatile oil component
eucalyptol
[no description available]		2.0610
methyl bromide
methyl bromide: used in ionization chambers, degreasing wool, extracting oils; insect fumigant; high concentrations can produce pulmonary edema,narcosis; chronic exposure can cause CNS depression,kidney injury; RN given refers to parent cpd; structure. bromomethane : A one-carbon compound in which the carbon is attached by single bonds to three hydrogen atoms and one bromine atom. It is produced naturally by marine algae.		2.0610bromohydrocarbon;
bromomethanes;
methyl halides		algal metabolite;
fumigant insecticide;
marine metabolite
linalool
linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.		2.0610monoterpenoid;
tertiary alcohol		antimicrobial agent;
fragrance;
plant metabolite;
volatile oil component
gamma-terpinene
gamma-terpinene: RN given refers to gamma-terpinene; structure. gamma-terpinene : One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.		2.0310cyclohexadiene;
monoterpene		antioxidant;
human xenobiotic metabolite;
plant metabolite;
volatile oil component
4-cymene
4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.		2.4720monoterpene;
toluenes		human urinary metabolite;
plant metabolite;
volatile oil component
citronellol
citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.		2.0610monoterpenoidplant metabolite
citronellyl acetate
citronellyl acetate: RN given refers to cpd without isomeric designation. citronellol acetate : A monoterpenoid that is the acetate ester of citronellol. It has been isolated from Citrus hystrix.		2.0610acetate ester;
monoterpenoid		plant metabolite
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.		2.0310terpineol;
tertiary alcohol		anti-inflammatory agent;
antibacterial agent;
antineoplastic agent;
antioxidant;
antiparasitic agent;
apoptosis inducer;
plant metabolite;
volatile oil component
terpinolene
[no description available]		2.0310p-menthadieneinsect repellent;
plant metabolite;
sedative;
volatile oil component
phosphine
phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.		2.0610mononuclear parent hydride;
phosphanes;
phosphine		carcinogenic agent;
fumigant insecticide
myrcene
myrcene: structure in first source. beta-myrcene : A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.		2.0610monoterpeneanabolic agent;
anti-inflammatory agent;
flavouring agent;
fragrance;
plant metabolite;
volatile oil component
citronellal, (r)-isomer
(R)-(+)-citronellal : The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).		2.0610citronellal
clotiazepam
2-carene: a monoterpene; structure in first source		2.0610monoterpenoid
isopulegol
isopulegol: isolated from Mentha cardiaca structure in first source		2.0610p-menthane monoterpenoidmetabolite
(+)-limonene
(4R)-limonene : An optically active form of limonene having (4R)-configuration.		2.0610limoneneplant metabolite
1-alpha-terpineol
(S)-(-)-alpha-terpineol : The (S)-enantiomer of alpha-terpineol.		2.4520alpha-terpineolplant metabolite
geraniol
[no description available]		2.06103,7-dimethylocta-2,6-dien-1-ol;
monoterpenoid;
primary alcohol		allergen;
fragrance;
plant metabolite;
volatile oil component
citral
citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.		2.0610enal;
monoterpenoid;
polyprenal		plant metabolite;
volatile oil component
geranyl acetate
geranyl acetate: constituted about 90% of the palmarosa oil. geranyl acetate : A monoterpenoid that is the acetate ester derivative of geraniol.		2.0610acetate ester;
monoterpenoid		plant metabolite
caryophyllene oxide
caryophyllene oxide: has butyrylcholinesterase inhibitory activity; structure in first source. epoxide : Any cyclic ether in which the oxygen atom forms part of a 3-membered ring.		2.0610epoxidemetabolite
caryophyllene
(-)-beta-caryophyllene : A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.. beta-caryophyllene : A sesquiterpene with a [7.2.0]-bicyclic structure comprising fused 9- and 4-membered rings, with a trans-ring junction, a trans-double bond between the 4- and 5-positions of the 9-membered ring, a methylidene group at position 9, and methyl groups at positions 3, 11, and 11. The most commonly occurring form is the (1R,9S)-(-)-enantiomer, which is found in many essential oils, particularly clove oil.. cannabinoid : A diverse group of pharmacologically active secondary metabolite characteristic to Cannabis plant as well as produced naturally in the body by humans and animals. Cannabinoids contain oxygen as a part of the heterocyclic ring or in the form of various functional groups. They are subdivided on the basis of their origin.		2.0610beta-caryophyllenefragrance;
insect attractant;
metabolite;
non-steroidal anti-inflammatory drug
borneol
[no description available]		2.0610borneol
ConditionIndicatedRelationship StrengthStudiesTrials