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α-Pinene

January 29, 2023

α-Pinene is an organic compound of the terpene class, one of two isomers of pinene.[2] It is an alkene and it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis) and Satureja myrtifolia (also known as Zoufa in some regions).[3][4] Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

α-Pinene
(+)-α-pinene
(−)-α-pinene
Names
IUPAC name
(1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-α-Pinene)
Identifiers
  • 80-56-8 unspecified Y
  • (+): 7785-70-8 Y
  • (−): 7785-26-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:36740 unspecified N
  • (+): CHEBI:28261 N
  • (−): CHEBI:28660 N
ChemSpider
  • 389795 Y
ECHA InfoCard 100.029.161
EC Number
  • (−): 232-077-3
KEGG
  • C06308 Y
  • 440968
RTECS number
  • DT7000000 (unspec. isomer)
UNII
  • JPF3YI7O34 unspecified Y
  • (+): H6CM4TWH1W Y
  • (−): TZR3GM95PR Y
  • DTXSID2029290
  • InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1 Y
    Key: GRWFGVWFFZKLTI-IUCAKERBSA-N Y
  • InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1
    Key: GRWFGVWFFZKLTI-IUCAKERBBG
  • C\1=C(\[C@@H]2C[C@H](C/1)C2(C)C)C
Properties
C10H16
Molar mass 136.238 g·mol−1
Appearance Clear colorless liquid
Density 0.858 g/mL (liquid at 20 °C)
Melting point −62.80 °C; −81.04 °F; 210.35 K[1]
Boiling point 156.85 ± 4.00 °C; 314.33 ± 7.20 °F; 430.00 ± 4.00 K[1]
Very low
Solubility in acetic acid Miscible
Solubility in ethanol Miscible
Solubility in acetone Miscible
−50.7° (1S,5S-Pinene)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
GHS labelling:
Danger
H226, H302, H304, H315, H317, H410
P210, P233, P240, P241, P242, P243, P261, P264, P270, P272, P273, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P321, P330, P331, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501
NFPA 704 (fire diamond)
1
2
0
Flash point 33 °C (91 °F; 306 K)
Related compounds
Related alkene
 β-pinene, camphene, 3-carene, limonene
Related compounds
 borneol, camphor, terpineol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Reactivity

 

Commercially important derivatives of alpha-pinene are linalool, geraniol, nerol, a-terpineol, and camphene.[5]

α-Pinene 1 is reactive owing to the presence of the four-membered ring adjacent to the alkene. The compound is prone to skeletal rearrangements such as the Wagner–Meerwein rearrangement. Acids typically lead to rearranged products. With concentrated sulfuric acid and ethanol the major products are terpineol 2 and its ethyl ether 3, while glacial acetic acid gives the corresponding acetate 4. With dilute acids, terpin hydrate 5 becomes the major product.

With one molar equivalent of anhydrous HCl, the simple addition product 6a can be formed at low temperature in the presence of diethyl ether, but it is very unstable. At normal temperatures, or if no ether is present, the major product is bornyl chloride 6b, along with a small amount of fenchyl chloride 6c.[6] For many years 6b (also called "artificial camphor") was referred to as "pinene hydrochloride", until it was confirmed as identical with bornyl chloride made from camphene. If more HCl is used, achiral 7 (dipentene hydrochloride) is the major product along with some 6b. Nitrosyl chloride followed by base leads to the oxime 8 which can be reduced to "pinylamine" 9. Both 8 and 9 are stable compounds containing an intact four-membered ring, and these compounds helped greatly in identifying this important component of the pinene skeleton.[7]

Under aerobic oxidation conditions, the main oxidation products are pinene oxide, verbenyl hydroperoxide, verbenol and verbenone.[8]

Atmospheric role

Monoterpenes, of which α-pinene is one of the principal species, are emitted in substantial amounts by vegetation, and these emissions are affected by temperature and light intensity. In the atmosphere α-pinene undergoes reactions with ozone, the hydroxyl radical or the NO3 radical,[9][full citation needed] leading to low-volatility species which partly condense on existing aerosols, thereby generating secondary organic aerosols. This has been shown in numerous laboratory experiments for the mono- and sesquiterpenes.[10][11] Products of α-pinene which have been identified explicitly are pinonaldehyde, norpinonaldehyde, pinic acid, pinonic acid and pinalic acid.

Properties and usage

α-Pinene is highly bioavailable with 60% human pulmonary uptake with rapid metabolism or redistribution.[12] α-Pinene is an anti-inflammatory via PGE1,[12] and is likely antimicrobial.[13] It exhibits activity as an acetylcholinesterase inhibitor, aiding memory.[12] Like borneol, verbenol and pinocarveol (−)-α-pinene is a positive modulator of GABAA receptors. It acts at the benzodiazepine binding site.[14]

α-Pinene forms the biosynthetic base for CB2 ligands, such as HU-308.[12]

α-Pinene is one of the many terpenes and terpenoids found in cannabis plants.[15] These compounds are also present in significant levels in the finished, dried cannabis flower preparation commonly known as marijuana.[16] It is widely theorized by scientists and cannabis experts alike that these terpenes and terpenoids contribute significantly to the unique "character" or "personality" of each marijuana strain's unique effects.[17] α-Pinene in particular is thought to reduce the memory deficits commonly reported as a side-effect of THC consumption. It likely demonstrates this activity due to its action as an acetylcholinesterase inhibitor, a class of compounds which are known to aid memory and increase alertness.[18]

α-Pinene also contributes significantly to many of the varied, distinct, and unique odor profiles of the multitude of marijuana strains, varieties and cultivars.[19]

References

  1. ^ a b "α-Pinene". from the original on 2018-01-30. Retrieved 2018-01-29.
  2. ^ Simonsen, J. L. (1957). The Terpenes. Vol. 2 (2nd ed.). Cambridge: Cambridge University Press. pp. 105–191.
  3. ^ PDR for Herbal Medicine. Montvale, NJ: Medical Economics Company. p. 1100.
  4. ^ Zebib, Bachar; Beyrouthy, Marc El; Sarfi, Carl; Merah, Othmane (2015-04-16). "Chemical Composition of the Essential Oil of Satureja myrtifolia (Boiss. & Hohen.) from Lebanon". Journal of Essential Oil-bearing Plants. 18 (1): 248–254. doi:10.1080/0972060X.2014.890075. ISSN 0972-060X. S2CID 95564601. from the original on 2016-08-04.
  5. ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  6. ^ Richter, G. H. (1945). "Textbook of Organic Chemistry" (2nd ed.). New York, NY: John Wiley & Sons: 663–666. {{cite journal}}: Cite journal requires |journal= (help)
  7. ^ Ružička, L.; Trebler, H. (1921). "Zur Kenntnis des Pinens. III. Konstitution des Nitrosopinens und seiner Umwandlungsprodukte" [On the science of pinene. III. Constitution of nitrosopinene and its transformation products]. Helvetica Chimica Acta. 4: 566–574. doi:10.1002/hlca.19210040161.
  8. ^ Neuenschwander, U. (2010). "Mechanism of the Aerobic Oxidation of α-Pinene". ChemSusChem (in German). 3 (1): 75–84. doi:10.1002/cssc.200900228. PMID 20017184.
  9. ^ IUPAC Subcommittee on Gas Kinetic Data Evaluation
  10. ^ Odum, J. R.; Hoffmann, T.; Bowman, F.; Collins, D.; Flagan, R. C.; Seinfeld, J. H. (1996). "Gas/particle partitioning and secondary organic aerosol yields". Environmental Science and Technology. 30 (8): 2580–2585. Bibcode:1996EnST...30.2580O. doi:10.1021/es950943+.
  11. ^ Donahue, N. M.; Henry, K. M.; Mentel, T. F.; Kiendler-Scharr, A.; Spindler, C.; Bohn, B.; Brauers, T.; Dorn, H. P.; Fuchs, H.; Tillmann, R.; Wahner, A.; Saathoff, H.; Naumann, K.-H.; Mohler, O.; Leisner, T.; Muller, L.; Reinnig, M.-C.; Hoffmann, T.; Salo, K.; Hallquist, M.; Frosch, M.; Bilde, M.; Tritscher, T.; Barmet, P.; Praplan, A. P.; DeCarlo, P. F.; Dommen, J.; Prevot, A. S. H.; Baltensperger, U. (2012). "Aging of biogenic secondary organic aerosol via gas-phase OH radical reactions". Proceedings of the National Academy of Sciences. 109 (34): 13503–13508. Bibcode:2012PNAS..10913503D. doi:10.1073/pnas.1115186109. PMC 3427056. PMID 22869714.
  12. ^ a b c d Russo, E. B. (2011). "Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects". British Journal of Pharmacology. 163 (7): 1344–1364. doi:10.1111/j.1476-5381.2011.01238.x. PMC 3165946. PMID 21749363.
  13. ^ Nissen, L.; Zatta, A.; Stefanini, I.; Grandi, S.; Sgorbati, B.; Biavati, B.; et al. (2010). "Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.)". Fitoterapia. 81 (5): 413–419. doi:10.1016/j.fitote.2009.11.010. PMID 19969046.
  14. ^ Yang, H.; Woo, J.; Pae, A.-N.; Um, M.-Y.; Cho, N.-C.; Park, K.-D.; Yoon, M.; Kim, J.; Lee, C.-J.; Cho, S. (2016). "α-Pinene, a major constituent of pine tree oils, enhances non-rapid eye movement sleep in mice through GABAA-benzodiazepine receptors". Molecular Pharmacology. 90 (5): 530–539. doi:10.1124/mol.116.105080. PMID 27573669.
  15. ^ Russo, E. B.; McPartland, J. M. (2003). "Cannabis is more than simply Δ9-tetrahydrocannabinol". Psychopharmacology. 165 (4): 431–432. doi:10.1007/s00213-002-1348-z. PMID 12491031. S2CID 19504014.
  16. ^ Turner, C. E.; Elsohly, M. A.; Boeren, E. G. (1980). "Constituents of Cannabis sativa L. XVII. A review of the natural constituents". Journal of Natural Products. 43 (2): 169–234. doi:10.1021/np50008a001. PMID 6991645.
  17. ^ Piomelli, D.; Russo, E. B. (2016). "The Cannabis sativa versus Cannabis indica debate: an interview with Ethan Russo, MD". Cannabis and Cannabinoid Research. 1 (1): 44–46. doi:10.1089/can.2015.29003.ebr. PMC 5576603. PMID 28861479.
  18. ^ Mahmoudvand, H.; Sheibani, V.; Keshavarz, H.; Shojaee, S.; Esmaeelpour, K.; Ziaali, N. (2016). "Acetylcholinesterase Inhibitor Improves Learning and Memory Impairment Induced by Toxoplasma gondii Infection". Iranian Journal of Parasitology. 11 (2): 177–185. PMC 5236094. PMID 28096851.
  19. ^ Mediavilla, V.; Steinemann, S. (1997). "Essential oil of Cannabis sativa L. strains". Journal of the International Hemp Association. 4: 80–82.

January 29, 2023
pinene, organic, compound, terpene, class, isomers, pinene, alkene, contains, reactive, four, membered, ring, found, oils, many, species, many, coniferous, trees, notably, pine, also, found, essential, rosemary, rosmarinus, officinalis, satureja, myrtifolia, a. a Pinene is an organic compound of the terpene class one of two isomers of pinene 2 It is an alkene and it contains a reactive four membered ring It is found in the oils of many species of many coniferous trees notably the pine It is also found in the essential oil of rosemary Rosmarinus officinalis and Satureja myrtifolia also known as Zoufa in some regions 3 4 Both enantiomers are known in nature 1S 5S or a pinene is more common in European pines whereas the 1R 5R or a isomer is more common in North America The racemic mixture is present in some oils such as eucalyptus oil and orange peel oil a Pinene a pinene a pineneNamesIUPAC name 1S 5S 2 6 6 Trimethylbicyclo 3 1 1 hept 2 ene a Pinene IdentifiersCAS Number 80 56 8 unspecified Y 7785 70 8 Y 7785 26 4 Y3D model JSmol Interactive imageChEBI CHEBI 36740 unspecified N CHEBI 28261 N CHEBI 28660 NChemSpider 389795 YECHA InfoCard 100 029 161EC Number 232 077 3KEGG C06308 YPubChem CID 440968RTECS number DT7000000 unspec isomer UNII JPF3YI7O34 unspecified Y H6CM4TWH1W Y TZR3GM95PR YCompTox Dashboard EPA DTXSID2029290InChI InChI 1S C10H16 c1 7 4 5 8 6 9 7 10 8 2 3 h4 8 9H 5 6H2 1 3H3 t8 9 m0 s1 YKey GRWFGVWFFZKLTI IUCAKERBSA N YInChI 1 C10H16 c1 7 4 5 8 6 9 7 10 8 2 3 h4 8 9H 5 6H2 1 3H3 t8 9 m0 s1Key GRWFGVWFFZKLTI IUCAKERBBGSMILES C 1 C C H 2C C H C 1 C2 C C CPropertiesChemical formula C 10H 16Molar mass 136 238 g mol 1Appearance Clear colorless liquidDensity 0 858 g mL liquid at 20 C Melting point 62 80 C 81 04 F 210 35 K 1 Boiling point 156 85 4 00 C 314 33 7 20 F 430 00 4 00 K 1 Solubility in water Very lowSolubility in acetic acid MiscibleSolubility in ethanol MiscibleSolubility in acetone MiscibleChiral rotation a D 50 7 1S 5S Pinene HazardsOccupational safety and health OHS OSH Main hazards FlammableGHS labelling PictogramsSignal word DangerHazard statements H226 H302 H304 H315 H317 H410Precautionary statements P210 P233 P240 P241 P242 P243 P261 P264 P270 P272 P273 P280 P301 P310 P301 P312 P302 P352 P303 P361 P353 P321 P330 P331 P332 P313 P333 P313 P362 P363 P370 P378 P391 P403 P235 P405 P501NFPA 704 fire diamond 120Flash point 33 C 91 F 306 K Related compoundsRelated alkene b pinene camphene 3 carene limoneneRelated compounds borneol camphor terpineolExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Reactivity 2 Atmospheric role 3 Properties and usage 4 ReferencesReactivity Edit Commercially important derivatives of alpha pinene are linalool geraniol nerol a terpineol and camphene 5 a Pinene 1 is reactive owing to the presence of the four membered ring adjacent to the alkene The compound is prone to skeletal rearrangements such as the Wagner Meerwein rearrangement Acids typically lead to rearranged products With concentrated sulfuric acid and ethanol the major products are terpineol 2 and its ethyl ether 3 while glacial acetic acid gives the corresponding acetate 4 With dilute acids terpin hydrate 5 becomes the major product With one molar equivalent of anhydrous HCl the simple addition product 6a can be formed at low temperature in the presence of diethyl ether but it is very unstable At normal temperatures or if no ether is present the major product is bornyl chloride 6b along with a small amount of fenchyl chloride 6c 6 For many years 6b also called artificial camphor was referred to as pinene hydrochloride until it was confirmed as identical with bornyl chloride made from camphene If more HCl is used achiral 7 dipentene hydrochloride is the major product along with some 6b Nitrosyl chloride followed by base leads to the oxime 8 which can be reduced to pinylamine 9 Both 8 and 9 are stable compounds containing an intact four membered ring and these compounds helped greatly in identifying this important component of the pinene skeleton 7 Under aerobic oxidation conditions the main oxidation products are pinene oxide verbenyl hydroperoxide verbenol and verbenone 8 Atmospheric role EditMonoterpenes of which a pinene is one of the principal species are emitted in substantial amounts by vegetation and these emissions are affected by temperature and light intensity In the atmosphere a pinene undergoes reactions with ozone the hydroxyl radical or the NO3 radical 9 full citation needed leading to low volatility species which partly condense on existing aerosols thereby generating secondary organic aerosols This has been shown in numerous laboratory experiments for the mono and sesquiterpenes 10 11 Products of a pinene which have been identified explicitly are pinonaldehyde norpinonaldehyde pinic acid pinonic acid and pinalic acid Properties and usage Edita Pinene is highly bioavailable with 60 human pulmonary uptake with rapid metabolism or redistribution 12 a Pinene is an anti inflammatory via PGE1 12 and is likely antimicrobial 13 It exhibits activity as an acetylcholinesterase inhibitor aiding memory 12 Like borneol verbenol and pinocarveol a pinene is a positive modulator of GABAA receptors It acts at the benzodiazepine binding site 14 a Pinene forms the biosynthetic base for CB2 ligands such as HU 308 12 a Pinene is one of the many terpenes and terpenoids found in cannabis plants 15 These compounds are also present in significant levels in the finished dried cannabis flower preparation commonly known as marijuana 16 It is widely theorized by scientists and cannabis experts alike that these terpenes and terpenoids contribute significantly to the unique character or personality of each marijuana strain s unique effects 17 a Pinene in particular is thought to reduce the memory deficits commonly reported as a side effect of THC consumption It likely demonstrates this activity due to its action as an acetylcholinesterase inhibitor a class of compounds which are known to aid memory and increase alertness 18 a Pinene also contributes significantly to many of the varied distinct and unique odor profiles of the multitude of marijuana strains varieties and cultivars 19 References Edit a b a Pinene Archived from the original on 2018 01 30 Retrieved 2018 01 29 Simonsen J L 1957 The Terpenes Vol 2 2nd ed Cambridge Cambridge University Press pp 105 191 PDR for Herbal Medicine Montvale NJ Medical Economics Company p 1100 Zebib Bachar Beyrouthy Marc El Sarfi Carl Merah Othmane 2015 04 16 Chemical Composition of the Essential Oil of Satureja myrtifolia Boiss amp Hohen from Lebanon Journal of Essential Oil bearing Plants 18 1 248 254 doi 10 1080 0972060X 2014 890075 ISSN 0972 060X S2CID 95564601 Archived from the original on 2016 08 04 Sell Charles S 2006 Terpenoids Kirk Othmer Encyclopedia of Chemical Technology doi 10 1002 0471238961 2005181602120504 a01 pub2 ISBN 0471238961 Richter G H 1945 Textbook of Organic Chemistry 2nd ed New York NY John Wiley amp Sons 663 666 a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help Ruzicka L Trebler H 1921 Zur Kenntnis des Pinens III Konstitution des Nitrosopinens und seiner Umwandlungsprodukte On the science of pinene III Constitution of nitrosopinene and its transformation products Helvetica Chimica Acta 4 566 574 doi 10 1002 hlca 19210040161 Neuenschwander U 2010 Mechanism of the Aerobic Oxidation of a Pinene ChemSusChem in German 3 1 75 84 doi 10 1002 cssc 200900228 PMID 20017184 IUPAC Subcommittee on Gas Kinetic Data Evaluation Odum J R Hoffmann T Bowman F Collins D Flagan R C Seinfeld J H 1996 Gas particle partitioning and secondary organic aerosol yields Environmental Science and Technology 30 8 2580 2585 Bibcode 1996EnST 30 2580O doi 10 1021 es950943 Donahue N M Henry K M Mentel T F Kiendler Scharr A Spindler C Bohn B Brauers T Dorn H P Fuchs H Tillmann R Wahner A Saathoff H Naumann K H Mohler O Leisner T Muller L Reinnig M C Hoffmann T Salo K Hallquist M Frosch M Bilde M Tritscher T Barmet P Praplan A P DeCarlo P F Dommen J Prevot A S H Baltensperger U 2012 Aging of biogenic secondary organic aerosol via gas phase OH radical reactions Proceedings of the National Academy of Sciences 109 34 13503 13508 Bibcode 2012PNAS 10913503D doi 10 1073 pnas 1115186109 PMC 3427056 PMID 22869714 a b c d Russo E B 2011 Taming THC potential cannabis synergy and phytocannabinoid terpenoid entourage effects British Journal of Pharmacology 163 7 1344 1364 doi 10 1111 j 1476 5381 2011 01238 x PMC 3165946 PMID 21749363 Nissen L Zatta A Stefanini I Grandi S Sgorbati B Biavati B et al 2010 Characterization and antimicrobial activity of essential oils of industrial hemp varieties Cannabis sativa L Fitoterapia 81 5 413 419 doi 10 1016 j fitote 2009 11 010 PMID 19969046 Yang H Woo J Pae A N Um M Y Cho N C Park K D Yoon M Kim J Lee C J Cho S 2016 a Pinene a major constituent of pine tree oils enhances non rapid eye movement sleep in mice through GABAA benzodiazepine receptors Molecular Pharmacology 90 5 530 539 doi 10 1124 mol 116 105080 PMID 27573669 Russo E B McPartland J M 2003 Cannabis is more than simply D9 tetrahydrocannabinol Psychopharmacology 165 4 431 432 doi 10 1007 s00213 002 1348 z PMID 12491031 S2CID 19504014 Turner C E Elsohly M A Boeren E G 1980 Constituents of Cannabis sativa L XVII A review of the natural constituents Journal of Natural Products 43 2 169 234 doi 10 1021 np50008a001 PMID 6991645 Piomelli D Russo E B 2016 The Cannabis sativa versus Cannabis indica debate an interview with Ethan Russo MD Cannabis and Cannabinoid Research 1 1 44 46 doi 10 1089 can 2015 29003 ebr PMC 5576603 PMID 28861479 Mahmoudvand H Sheibani V Keshavarz H Shojaee S Esmaeelpour K Ziaali N 2016 Acetylcholinesterase Inhibitor Improves Learning and Memory Impairment Induced by Toxoplasma gondii Infection Iranian Journal of Parasitology 11 2 177 185 PMC 5236094 PMID 28096851 Mediavilla V Steinemann S 1997 Essential oil of Cannabis sativa L strains Journal of the International Hemp Association 4 80 82 Retrieved from https en wikipedia org w index php title A Pinene amp oldid 1127986752, wikipedia, wiki, book, books, library,

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