| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:29:40 UTC |
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| Updated at | 2020-12-07 19:07:20 UTC |
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| CannabisDB ID | CDB000300 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | α-pinene |
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| Description | Alpha-Pinene, also known as 2-pinene or acintene A, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-pinene is considered to be an isoprenoid lipid molecule. There are two isomers of alpha-Pinene: (−)-α-pinene and (+)-α-pinene. The (−)-α-pinene isomer is more common in European pines, whereas the (+)-α-isomer is more common in North America. alpha-Pinene is a neutral, hydrophobic molecule, practically insoluble in water. It exists as a clear, colorless oil. Alpha-pinene has a woody, camphoreous, piney or turpentine-like odor and a spicy, woody or herbal taste. It is widely used as a flavor and a fragrance additive and has one of the lowest boiling points of all monoterpenes. Industrially, α-pinene is largely used as starting material for the synthesis of terpineol, camphor, borneol and terpene resin, synthetic perfumes and resins, medicines and other synthetic organic chemicals. Alpha-pinene is found naturally in the essential oils and resins of many coniferous tree species, notably the pine (where it gets its name) as well as in non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush (Artemisia tridentata). It is also found in the essential oil of rosemary, eucalyptus oil and orange peel oil. α-Pinene is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645 ) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. α-Pinene, in particular, contributes significantly to many of the varied, distinct, and unique odor profiles of different cannabis strains, varieties and cultivars. Monoterpenes, of which α-pinene is one of the principal species, are emitted in substantial amounts by vegetation. In the atmosphere α-pinene undergoes reactions with ozone, hydroxyl radicals and NO3 radicals to produce several compounds including: pinonaldehyde, norpinonaldehyde, pinic acid, pinonic acid and pinalic acid (PMID: 20017184 ). α-Pinene exhibits a wide range of physiological or drug like effects. There are well-substantiated claims that has anticoagulant, antitumor, antimicrobial, antimalarial, antioxidant, anti-inflammatory, anti-Leishmania, analgesic, gastroprotective, anxiolytic, cytoprotective, anticonvulsant, and neuroprotective effects (PMID: 31739596 ). α-Pinene exhibits activity as an acetylcholinesterase inhibitor, which may aid in memory retention. α-Pinene, in particular, is thought to reduce the memory deficits commonly reported as a side-effect of THC consumption (PMID: 31739596 ). α-Pinene is a positive modulator of GABAA receptors and binds to the benzodiazepine binding site of the GABAA receptor (PMID: 31739596 ). (+)-α-Pinene also binds to Cytochrome P450 2B6 and is a potent inhibitor of this enzyme (PMID: 23786449 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (+)-3,6,6-TRIMETHYLBICYCLO[3.1.1]hept-2-ene | ChEBI | | (1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene | ChEBI | | (1R,5R)-alpha-Pinene | ChEBI | | alpha-Pinene(dextro) | ChEBI | | (1R,5R)-a-Pinene | Generator | | (1R,5R)-Α-pinene | Generator | | a-Pinene(dextro) | Generator | | Α-pinene(dextro) | Generator | | (+)-a-Pinene | Generator | | (+)-Α-pinene | Generator | | (+)-(1R)-alpha-Pinene | HMDB | | (+)-(1R)-α-Pinene | HMDB | | (+)-(1R,5R)-alpha-Pinene | HMDB | | (+)-(1R,5R)-α-Pinene | HMDB | | (+)-2-Pinene | HMDB | | (+)-alpha-Pinene | HMDB | | (1R)-(+)-alpha-Pinene | HMDB | | (1R)-(+)-α-Pinene | HMDB | | (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene | HMDB | | (1R)-alpha-Pinene | HMDB | | (1R)-α-Pinene | HMDB | | (1R,5R)-(+)-alpha-Pinene | HMDB | | (1R,5R)-(+)-α-Pinene | HMDB | | (R)-(+)-alpha-Pinene | HMDB | | (R)-(+)-α-Pinene | HMDB | | (±)-2-Pinene | HMDB | | (±)-alpha-Pinene | HMDB | | (±)-α-Pinene | HMDB | | 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene | HMDB | | 2-Pinene | HMDB | | alpha-Pinene | HMDB | | α-Pinene | HMDB | | (1R,5R)-(+)-2-Pinene | PhytoBank | | d-alpha-Pinene | PhytoBank | | d-α-Pinene | PhytoBank |
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| Chemical Formula | C10H16 |
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| Average Molecular Weight | 136.23 |
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| Monoisotopic Molecular Weight | 136.1252 |
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| IUPAC Name | (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene |
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| Traditional Name | (+)-α-pinene |
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| CAS Registry Number | 7785-70-8 |
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| SMILES | CC1=CC[C@@H]2C[C@H]1C2(C)C |
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| InChI Identifier | InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1 |
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| InChI Key | GRWFGVWFFZKLTI-RKDXNWHRSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Monoterpenoids |
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| Direct Parent | Bicyclic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Pinane monoterpenoid
- Bicyclic monoterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Industrial application: Biological role: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -62 °C | Not Available | | Boiling Point | 155 to 156 °C | Wikipedia | | Water Solubility | Not Available | Not Available | | logP | 4.44 | GRIFFIN,S ET AL. (1999) |
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| Predicted Properties | [] |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| GC-MS | α-pinene, non-derivatized, GC-MS Spectrum | splash10-0006-9100000000-efa1a7d8bd0221192f0d | Spectrum | | GC-MS | α-pinene, non-derivatized, GC-MS Spectrum | splash10-0006-9100000000-efa1a7d8bd0221192f0d | Spectrum | | Predicted GC-MS | α-pinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0079-1900000000-7a79889acc60a4543bcf | Spectrum | | Predicted GC-MS | α-pinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-89e84f859d8f1f97d5c2 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-fb8d56b761aae12a505c | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dr-0900000000-bfe7e4ba927cd83956b4 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-5e150dd4370565464dad | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-5e150dd4370565464dad | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kr-0900000000-b5dcbaea24fd03f1cbf9 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-0900000000-1a368fcdf84da3da6f72 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-32bfa268614bcd6c4f81 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-32bfa268614bcd6c4f81 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-0900000000-eb6403ceb156dbbc7ce8 | 2021-09-25 | View Spectrum |
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| General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
- Neuenschwander U, Guignard F, Hermans I: Mechanism of the aerobic oxidation of alpha-pinene. ChemSusChem. 2010;3(1):75-84. doi: 10.1002/cssc.200900228. [PubMed:20017184 ]
- Salehi B, Upadhyay S, Erdogan Orhan I, Kumar Jugran A, L D Jayaweera S, A Dias D, Sharopov F, Taheri Y, Martins N, Baghalpour N, Cho WC, Sharifi-Rad J: Therapeutic Potential of alpha- and beta-Pinene: A Miracle Gift of Nature. Biomolecules. 2019 Nov 14;9(11). pii: biom9110738. doi: 10.3390/biom9110738. [PubMed:31739596 ]
- Wilderman PR, Shah MB, Jang HH, Stout CD, Halpert JR: Structural and thermodynamic basis of (+)-alpha-pinene binding to human cytochrome P450 2B6. J Am Chem Soc. 2013 Jul 17;135(28):10433-40. doi: 10.1021/ja403042k. Epub 2013 Jul 3. [PubMed:23786449 ]
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