Page last updated: 2024-09-20

alpha-pinene

Cross-References

ID SourceID
PubMed CID6654
CHEMBL ID442565
CHEBI ID36740
MeSH IDM0047005

Synonyms (97)

Synonym
LS-13835
.alpha.-pinene
2-pinene
nsc7727
80-56-8
bicyclo[3.1.1]hept-2-ene,6,6-trimethyl-
2,6-trimethylbicyclo[3.1.1]-2-heptene
2,6-trimethylbicyclo[3.1.1]-2-hept-2-ene
nsc-7727
pinene isomer
pinene, alpha
NSC94522 ,
NSC94523 ,
alpha [d] pinene
alpha [l] pinene
(r)-.alpha.-pinene
1r-.alpha.-pinene
bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-
(1r)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
(+/-)-2-pinene
pin-2(3)-ene
2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
cyclic dexadiene
acitene a
(+/-)-alpha-pinene
acintene a
2,6,6-trimethylbicyclo(3.1.1)-2-hept-2-ene
nsc 7727
2,6,6-trimethylbicyclo(3.1.1)hept-2-ene
pinene, alpha (d)
pinene, alpha (l)
nsc-94522
nsc-94523
NCGC00090682-01
alpha-pinene ,
C09880
(+-)-2-pinene
(+-)-alpha-pinene
CHEBI:36740 ,
pin-2-ene
4,6,6-trimethylbicyclo[3.1.1]hept-3-ene
pc-500(terpene)
sylvapine a
alfa-pinene
leavo-95
CHEMBL442565
pc-500
AKOS000121239
A839247
NCGC00090682-02
4,6,6-trimethylbicyklo(3,1,1)hept-3-en
cas-80-56-8
dtxcid006501
tox21_303385
dtxsid4026501 ,
NCGC00257379-01
NCGC00257662-01
tox21_200108
tox21_110996
25766-18-1
FT-0604414
FT-0622197
FT-0604379
alphapinene
alpha pinene
Q-201582
(3z)-5-methyl-1h-indole-2,3-dione3-oxime
2,6,6-trimethyl-bicyclo[3.1.1]hept-2-ene
un 2368
pc 500
bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (.+/-.)-
2,6,6-trimethylbicyclo[3.1.1]-2-heptene
(.+/-.)-.alpha.-pinene
pinene, .alpha.
FT-0698080
alpha.-pinene
alpha-pinene (+/-)-alpha-pinene
DB15573
(-)-?-pinene
Q27104380
AMY22338
an alpha-pinene
(-)alpha-pinene
AB86235
AB86464
AB93066
EN300-21685
(+/-)-2-pinene, 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene, alpha-pinene
alpha -pinene
2,6,6-trimethylbicyclo(3.1.1)-2-heptene
pinene (alpha)
trimethyl bicyclo (3.1.1) hept-2-ene
pesticide code: 067004.
bicyclo(3.1.1)hept-2-ene,2,6,6-trimethyl-2-pinene
alpha-pinene, (+/-)-
australene
2,6,6-trimethylbicyclo (3.1.1)hept-2-ene, 9cl

Roles (1)

RoleDescription
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 (1)

ClassDescription
pinene
[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)

alpha-pinene is involved in 1 pathway(s), involving a total of 2 unique proteins and 10 unique compounds

PathwayProteinsCompounds
Limonene and Pinene Degradation210

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency0.18980.006038.004119,952.5996AID1159521
thyroid stimulating hormone receptorHomo sapiens (human)Potency6.30960.001318.074339.8107AID926; AID938
mitogen-activated protein kinase 1Homo sapiens (human)Potency39.81070.039816.784239.8107AID995
Nuclear receptor ROR-gammaHomo sapiens (human)Potency42.16320.026622.448266.8242AID651802
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
xenobiotic metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of glucose metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of steroid metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
intracellular receptor signaling pathwayNuclear receptor ROR-gammaHomo sapiens (human)
circadian regulation of gene expressionNuclear receptor ROR-gammaHomo sapiens (human)
cellular response to sterolNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of circadian rhythmNuclear receptor ROR-gammaHomo sapiens (human)
regulation of fat cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear receptor ROR-gammaHomo sapiens (human)
adipose tissue developmentNuclear receptor ROR-gammaHomo sapiens (human)
T-helper 17 cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
protein bindingNuclear receptor ROR-gammaHomo sapiens (human)
oxysterol bindingNuclear receptor ROR-gammaHomo sapiens (human)
zinc ion bindingNuclear receptor ROR-gammaHomo sapiens (human)
ligand-activated transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
sequence-specific double-stranded DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
nuclear receptor activityNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
nucleoplasmNuclear receptor ROR-gammaHomo sapiens (human)
nuclear bodyNuclear receptor ROR-gammaHomo sapiens (human)
chromatinNuclear receptor ROR-gammaHomo sapiens (human)
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID1103226Induction of growth of Fusarium graminearum after 4 to 12 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID1103228Antimicrobial activity against Pseudomonas aeruginosa ATCC 9027 assessed as growth inhibition after 24 hr by broth microdilution method2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID1103229Antimicrobial activity against Escherichia coli ATCC 8739 assessed as growth inhibition after 24 hr by broth microdilution method2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID334964Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 20 mg/kg, ip administered 1 hr before carrageenan challenge measured after 1 hrs
AID334963Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 40 mg/kg, ip administered 1 hr before carrageenan challenge measured after 5 hrs
AID334965Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 20 mg/kg, ip administered 1 hr before carrageenan challenge measured after 3 hrs
AID334962Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 40 mg/kg, ip administered 1 hr before carrageenan challenge measured after 3 hrs
AID360503Antioxidant activity assessed as DPPH radical scavenging activity1995Journal of natural products, Nov, Volume: 58, Issue:11
Santolindiacetylene, a polyacetylene derivative isolated from the essential oil of Santolina canescens.
AID334960Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 80 mg/kg, ip administered 1 hr before carrageenan challenge measured after 5 hrs
AID1103236Antifungal activity against Botryotinia fuckeliana assessed as mycelial growth inhibition after 4 to 12 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID334961Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 40 mg/kg, ip administered 1 hr before carrageenan challenge measured after 1 hrs
AID1103234Antifungal activity against Fusarium graminearum assessed as mycelial growth inhibition after 4 to 12 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID1103231Antimicrobial activity against Staphylococcus aureus ATCC 6538 assessed as growth inhibition after 24 hr by broth microdilution method2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID1066526Antiinflammatory activity against human primary chondrocytes assessed as inhibition of IL-1beta-induced NO production at 200 ug/ml after 30 mins by Griess method relative to IL-1beta treated control2014Journal of natural products, Feb-28, Volume: 77, Issue:2
Anti-inflammatory and chondroprotective activity of (+)-α-pinene: structural and enantiomeric selectivity.
AID1103232Antifungal activity against Rhizoctonia solani assessed as mycelial growth inhibition after 4 to 12 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID334958Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 80 mg/kg, ip administered 1 hr before carrageenan challenge measured after 1 hrs
AID1103230Antimicrobial activity against Staphylococcus epidermidis ATCC 12228 assessed as growth inhibition after 24 hr by broth microdilution method2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID334959Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 80 mg/kg, ip administered 1 hr before carrageenan challenge measured after 3 hrs
AID334966Antiinflammatory activity against carrageenan-induced plantar edema in Wistar rat hind paw at 20 mg/kg, ip administered 1 hr before carrageenan challenge measured after 5 hrs
AID1103235Antifungal activity against Fusarium oxysporum f. sp. lycopersici assessed as mycelial growth inhibition after 4 to 12 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
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.
AID1103227Antimicrobial activity against Candida albicans ATCC 14053 assessed as growth inhibition after 24 hr by broth microdilution method2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID1103233Antifungal activity against Fusarium culmorum assessed as mycelial growth inhibition after 4 to 12 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (783)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (2.17)18.7374
1990's35 (4.47)18.2507
2000's197 (25.16)29.6817
2010's424 (54.15)24.3611
2020's110 (14.05)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.25%)5.53%
Reviews14 (1.75%)6.00%
Case Studies1 (0.13%)4.05%
Observational0 (0.00%)0.25%
Other782 (97.87%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (15)

ArticleYear
Neuroprotective effect of α-pinene self-emulsifying nanoformulation against 6-OHDA induced neurotoxicity on human SH-SY5Y cells and its in vivo validation for anti-Parkinson's effect.
Journal of biochemical and molecular toxicology, Volume: 35, Issue: 11
2021
Contact Toxicity and Repellency of the Essential Oils of Evodia lenticellata Huang and Evodia rutaecarpa (Juss.) Benth. Leaves against Three Stored Product Insects.
Journal of oleo science, Aug-01, Volume: 67, Issue: 8
2018
Potential protective effects of alpha-pinene against cytotoxicity caused by aspirin in the IEC-6 cells.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, Volume: 93
2017
Assessment of safe bioactive doses of Foeniculum vulgare Mill. essential oil from Portugal.
Natural product research, Volume: 31, Issue: 22
2017
Toxicity of Monoterpene Structure, Diversity and Concentration to Mountain Pine Beetles, Dendroctonus ponderosae: Beetle Traits Matter More.
Journal of chemical ecology, Volume: 43, Issue: 4
2017
Chemical composition, toxicity and non-target effects of Pinus kesiya essential oil: An eco-friendly and novel larvicide against malaria, dengue and lymphatic filariasis mosquito vectors.
Ecotoxicology and environmental safety, Volume: 129
2016
Chemical composition, protoscolicidal effects and acute toxicity of Pistacia atlantica Desf. fruit extract.
Natural product research, Volume: 30, Issue: 10
2016
Antileishmanial and cytotoxic effects of essential oil and methanolic extract of Myrtus communis L.
The Korean journal of parasitology, Volume: 53, Issue: 1
2015
Myrtus communis L. as source of a bioactive and safe essential oil.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, Volume: 75
2015
Essential oil of Juniperus communis subsp. alpina (Suter) Čelak needles: chemical composition, antifungal activity and cytotoxicity.
Phytotherapy research : PTR, Volume: 26, Issue: 9
2012
Genotoxicity of citrus wastewater in prokaryotic and eukaryotic cells and efficiency of heterogeneous photocatalysis by TiO(2).
Journal of photochemistry and photobiology. B, Biology, Mar-01, Volume: 108
2012
Direct VUV photodegradation of gaseous α-pinene in a spiral quartz reactor: intermediates, mechanism, and toxicity/biodegradability assessment.
Chemosphere, Volume: 81, Issue: 9
2010
Cytotoxicity and genotoxicity in human lung epithelial A549 cells caused by airborne volatile organic compounds emitted from pine wood and oriented strand boards.
Toxicology letters, Jun-16, Volume: 196, Issue: 1
2010
Toxicity study of the volatile constituents of Myoga utilizing acute dermal irritation assays and the Guinea-pig Maximization test.
Journal of occupational health, Volume: 48, Issue: 6
2006
Effects of volatile oil constituents of Nigella sativa on carbon tetrachloride-induced hepatotoxicity in mice: evidence for antioxidant effects of thymoquinone.
Research communications in molecular pathology and pharmacology, Volume: 110, Issue: 3-4
2001
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (3)

ArticleYear
In Silico Prediction of Selected Bioactive Compounds Present in Alpinia elegans (C.Presl) K.Schum Seed Oil as Potential Drug Candidates Against Human Cancer Cell Lines.
Asian Pacific journal of cancer prevention : APJCP, Aug-01, Volume: 24, Issue: 8
2023
Formulation and Evaluation of α-Pinene Loaded Self-emulsifying Nanoformulation for
Recent patents on nanotechnology, Volume: 16, Issue: 2
2022
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology, Volume: 96, Issue: 5
2019
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (6)

ArticleYear
Key essential oil components delocalize Candida albicans Kar3p and impact microtubule structure.
Microbiological research, Volume: 272
2023
Effects of α-pinene on life history traits and stress tolerance in the springtail Folsomia candida.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, Volume: 229
2020
Southern Pine Beetle (Coleoptera: Curculionidae: Scolytinae) Pheromone Component trans-Verbenol: Enantiomeric Specificity and Potential as a Lure Adjuvant.
Environmental entomology, 02-13, Volume: 48, Issue: 1
2019
Portable photocatalytic air cleaners: efficiencies and by-product generation.
Environmental science and pollution research international, Volume: 23, Issue: 8
2016
Protective effects of mastic oil from Pistacia lentiscus variation chia against experimental growth of lewis lung carcinoma.
Nutrition and cancer, Volume: 61, Issue: 5
2009
Elimination of plant toxins by herbivorous woodrats: revisiting an explanation for dietary specialization in mammalian herbivores.
Oecologia, Volume: 134, Issue: 1
2003
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (1)

ArticleYear
Detection of Mildewed Nutmeg Internal Quality during Storage Using an Electronic Nose Combined with Chemical Profile Analysis.
Molecules (Basel, Switzerland), Aug-14, Volume: 28, Issue: 16
2023
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]