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{{chembox |
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{{chembox |
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| verifiedrevid = 443508287 |
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| verifiedrevid = 460021442 |
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| Name = Caryophyllene |
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| Name = Caryophyllene |
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| ImageFile1 = Beta-Caryophyllen.svg |
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| ImageFile = |
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<!-- | ImageSize = 200px --> |
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| ImageFile1 = Beta-Caryophyllen.svg |
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| ImageName = beta-caryophyllene |
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| ImageName = beta-caryophyllene |
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| IUPACName = 4,11,11-trimethyl-8-methylene-<br />bicycloundec-4-ene |
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| OtherNames = β-Caryophyllene; <br> trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicycloundec-4-ene |
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| PIN = (1''R'',4''E'',9''S'')-4,11,11-Trimethyl-8-methylidenebicycloundec-4-ene |
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| SystematicName = |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = β-Caryophyllene<br />''trans''-(1''R'',9''S'')-8-Methylene-4,11,11-trimethylbicycloundec-4-ene |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| IUPACName = |
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|Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4444848 |
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| ChemSpiderID = 4444848 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 445740 |
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| ChEMBL = 445740 |
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| DrugBank = DB16854 |
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| EC_number = 201-746-1 |
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| KEGG = C09629 |
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| PubChem = 5281515 |
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| PubChem = 5281515 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 87-44-5 |
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| CASNo = 87-44-5 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 10357 |
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| ChEBI = 10357 |
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| SMILES = C1(=C)\CC/C=C(/CC21CC2(C)C)C |
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| SMILES = C1(=C)\CC/C=C(/CC21CC2(C)C)C |
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| Section2 = {{Chembox Properties |
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|Section2 = {{Chembox Properties |
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| C=15 |
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| Formula = C<sub>15</sub>H<sub>24</sub> |
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| H=24 |
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| MolarMass = 204.36 g/mol |
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| Density = 0.9052 g/cm<sup>3</sup> |
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| Density = 0.9052 g/cm<sup>3</sup> (17 °C)<ref>] Record, CAS Registry Number 87-44-5</ref> |
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| MeltingPt = |
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| BoilingPt = 262-264 °C; 129-130 °C (14 mm Hg) |
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| BoilingPtC = 262 - 264 |
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| BoilingPt_ref= <ref>{{cite journal | last = Baker | first = R. R. | journal = Journal of Analytical and Applied Pyrolysis | date = 2004 | volume = 71 | issue = 1 | pages = 223–311 | doi=10.1016/s0165-2370(03)00090-1 | title=The pyrolysis of tobacco ingredients| bibcode = 2004JAAP...71..223B }}</ref> |
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|Section6 = {{Chembox Hazards |
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| GHSPictograms = {{GHS07}}{{GHS08}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|304|317}} |
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| PPhrases = {{P-phrases|261|272|280|301+316|302+352|321|331|333+317|362+364|405|501}} |
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'''Caryophyllene''' ({{IPAc-en|ˌ|k|ær|i|oʊ-|ˈ|f|ɪ|l|iː|n}}), more formally '''(−)-β-caryophyllene''' ('''BCP'''), is a natural bicyclic ] that occurs widely in nature. Caryophyllene is notable for having a ] ring, as well as a ''trans''-double bond in a 9-membered ring, both rarities in nature. <ref name=KO>{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}</ref> |
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'''Caryophyllene''' ({{pron-en|ˌkæri.ɵfɪˈliːn}}), or (−)-β-caryophyllene, is a natural bicyclic ] that is a constituent of many ]s, especially clove oil, the oil from the stems and flowers of '']'' (cloves)<ref name="pmid11482764">{{cite journal |author=Ghelardini C, Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A |title=Local anaesthetic activity of beta-caryophyllene |journal=Farmaco |volume=56 |issue=5–7 |pages=387–9 |year=2001 |pmid=11482764 |doi= 10.1016/S0014-827X(01)01092-8|url=}}</ref>, the essential oil of hemp '']''<ref name="pmid18574142"/>, rosemary '']''<ref name="pmid18670820"/>, and ]<ref> Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. <http://realbeer.com/hops/aroma.html> Accessed July 21, 2010.</ref>. It is usually found as a mixture with isocaryophyllene (the ''cis'' double bond isomer) and ] (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a ] ring, a rarity in nature. |
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== Production == |
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Caryophyllene is one of the chemical compounds that contributes to the spiciness of ]. In a study conducted by Jürg Gertsch et al. from the Swiss Federal Institute of Technology (]), beta-caryophyllene was shown to selectively bind to the ] type-2 (]) and to exert significant cannabimimetic ] effects in mice.<ref name="pmid18574142">{{cite journal |author=Gertsch J, Leonti M, Raduner S, ''et al.'' |title=Beta-caryophyllene is a dietary cannabinoid |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=105 |issue=26 |pages=9099–104 |year=2008 |month=July |pmid=18574142 |pmc=2449371 |doi=10.1073/pnas.0803601105}}</ref> Since the widespread plant natural product beta-caryophyllene is an FDA approved food additive and ingested daily with food it is the first dietary cannabinoid. Whether this compound is able to modulate inflammatory processes in humans via the ] is yet unknown. Beta-caryophyllene does not bind to the centrally expressed cannabinoid receptor type-1 (]) and therefore does not exert psychomimetic effects. |
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Caryophyllene can be produced synthetically,<ref>{{cite journal |last1=Corey |first1=E. J. |last2=Mitra |first2=R. B. |last3=Uda |first3=H. |title=Total Synthesis of ''d'',''l''-Caryophyllene and ''d'',''l''-Isocaryophyllene |journal=Journal of the American Chemical Society |year=1964 |volume=86 |issue=3 |pages=485–492 |doi=10.1021/ja01057a040|bibcode=1964JAChS..86..485C }}</ref> but it is invariably obtained from natural sources because it is widespread. It is a constituent of many ]s, especially clove oil, the oil from the stems and flowers of '']'' (cloves), the essential oil of '']'', ], ], and ].<ref name=KO/> It is usually found as a mixture with ] (the ''cis'' double bond isomer) and ] (obsolete name: α-caryophyllene), a ring-opened isomer. |
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Caryophyllene is one of the chemical compounds that contributes to the ] of ].<ref name="pmid12462618">{{cite journal |last1=Jirovetz |first1=L. |last2=Buchbauer |first2=G. |last3=Ngassoum |first3=M. B. |last4=Geissler |first4=M. |title=Aroma compound analysis of ''Piper nigrum'' and ''Piper guineense'' essential oils from Cameroon using solid-phase microextraction–gas chromatography, solid-phase microextraction–gas chromatography–mass spectrometry and olfactometry |journal=Journal of Chromatography A |volume=976 |issue=1–2 |pages=265–275 |date=November 2002 |pmid=12462618 |doi= 10.1016/S0021-9673(02)00376-X}}</ref> |
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The first total synthesis of caryophyllene in 1964 by ] was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.<ref>{{cite journal |author=Corey EJ, Mitra RB, Uda H |title=Total Synthesis of ''d'',''l''-Caryophyllene and ''d'',''l''-Isocaryophyllene |journal=Journal of the American Chemical Society |year=1964 |volume=86 |issue=3 |pages=485–492 |doi=10.1021/ja01057a040}}</ref> |
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== Basic research == |
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β-Caryophyllene is under ] for its potential action as an agonist of the ] (CB<sub>2</sub> receptor).<ref name="Ceccarelli Fiorenzani Pessina et al 2020">{{cite journal |last1=Ceccarelli |first1=Ilaria |last2=Fiorenzani |first2=Paolo |last3=Pessina |first3=Federica |last4=Pinassi |first4=Jessica |last5=Aglianò |first5=Margherita |last6=Miragliotta |first6=Vincenzo |last7=Aloisi |first7=Anna Maria |title=The CB2 Agonist β-Caryophyllene in Male and Female Rats Exposed to a Model of Persistent Inflammatory Pain |journal=Frontiers in Neuroscience |date=18 August 2020 |volume=14 |pages=850 |doi=10.3389/fnins.2020.00850| pmc=7461959 |pmid=33013287 |doi-access=free }}</ref> In other basic studies, β-caryophyllene has a binding affinity of K<sub>i</sub> = 155 nM at the CB<sub>2</sub> receptors.<ref>{{cite journal |last1=Alberti |first1=Thaís Barbosa |last2=Barbosa |first2=Wagner Luiz Ramos |last3=Vieira |first3=José Luiz Fernandes |last4=Raposo |first4=Nádia Rezende Barbosa |last5=Dutra |first5=Rafael Cypriano |title=(−)-β-Caryophyllene, a CB2 Receptor-Selective Phytocannabinoid, Suppresses Motor Paralysis and Neuroinflammation in a Murine Model of Multiple Sclerosis |journal=International Journal of Molecular Sciences |date=1 April 2017 |volume=18 |issue=4 |pages=691 |doi=10.3390/ijms18040691 |pmid=28368293 |pmc=5412277 |doi-access=free }}</ref> |
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β-Caryophyllene has the highest cannabinoid activity compared to the ring opened isomer α-caryophyllene ] which may modulate CB<sub>2</sub> activity.<ref>{{cite journal |last1=Hashiesh |first1=Hebaallah Mamdouh |last2=Sharma |first2=Charu |last3=Goyal |first3=Sameer N. |last4=Sadek |first4=Bassem |last5=Jha |first5=Niraj Kumar |last6=Kaabi |first6=Juma Al |last7=Ojha |first7=Shreesh |title=A focused review on CB2 receptor-selective pharmacological properties and therapeutic potential of β-caryophyllene, a dietary cannabinoid |journal=Biomedicine & Pharmacotherapy |date=1 August 2021 |volume=140 |pages=111639 |doi=10.1016/j.biopha.2021.111639 |pmid=34091179 |s2cid=235362290 |doi-access=free }}</ref> To compare binding, ] binds to the CB<sub>2</sub> receptors as a partial agonist with an affinity of K<sub>i</sub> = 126.4 nM,<ref>{{cite book |last1=Russo |first1=Ethan B. |last2=Marcu |first2=Jahan |title=Cannabinoid Pharmacology |chapter=Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads |series=Advances in Pharmacology |date=2017 |volume=80 |pages=67–134 |doi=10.1016/bs.apha.2017.03.004 |pmid=28826544 |isbn=978-0-12-811232-8 }}</ref> while delta-9-] binds to the CB<sub>2</sub> receptors as a partial agonist with an affinity of K<sub>i</sub> = 36 nM.<ref>{{cite journal |last1=Bow |first1=Eric W. |last2=Rimoldi |first2=John M. |title=The Structure–Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation |journal=Perspectives in Medicinal Chemistry |date=28 June 2016 |volume=8 |pages=17–39 |doi=10.4137/PMC.S32171 |pmid=27398024 |pmc=4927043 }}</ref> |
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== Safety == |
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Caryophyllene has been given ] (GRAS) designation by the FDA and is approved by the FDA for use as a food additive, typically for flavoring.<ref>{{cite web |title=Nomination Background: beta-Caryophyllene (CASRN: 87-44-5) |url=https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/chem_background/exsumpdf/betacaryophyllene_508.pdf }}</ref><ref name="accessdata.fda.gov">{{Cite web|url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.515&SearchTerm=caryophyllene|title = CFR - Code of Federal Regulations Title 21}}</ref> Rats given up to 700 mg/kg daily for 90 days did not produce any significant toxic effects.<ref>{{cite journal | doi=10.1177/1091581816655303 | title=Toxicological Evaluation of β-Caryophyllene Oil | year=2016 | last1=Schmitt | first1=D. | last2=Levy | first2=R. | last3=Carroll | first3=B. | journal=International Journal of Toxicology | volume=35 | issue=5 | pages=558–567 | pmid=27358239 | s2cid=206689471 | doi-access=free }}</ref> Caryophyllene has an {{LD50}} of 5,000 mg/kg in mice.<ref>{{Cite web |title=β-Caryophyllene - SDS |url=https://www.sigmaaldrich.com/AU/en/sds/ALDRICH/W225207?userType=undefined |access-date=18 April 2024}}</ref><ref>{{Cite web |title=Oil of cinnamon - SDS |url=https://www.carlroth.com/medias/SDB-A432-AU-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wyNzQzMDV8YXBwbGljYXRpb24vcGRmfHNlY3VyaXR5RGF0YXNoZWV0cy9oOWMvaDAyLzkwMjM0NDcyNjk0MDYucGRmfGI0MTk3NmNjN2U0Yjg4NjU2NWNmYWY2YWRkMTQzNjM0OWQxNGYxMmU2N2NlYzMyMTY0ZjljZWQ5YzRhM2YzYmY |access-date=18 April 2024}}</ref> |
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== Metabolism and derivatives== |
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14-Hydroxycaryophyllene oxide (]<sub>15</sub>]<sub>24</sub>]<sub>2</sub>) was isolated from the urine of ]s treated with (−)-caryophyllene (C<sub>15</sub>H<sub>24</sub>). The ] ] of 14-hydroxycaryophyllene (as its ] derivative) has been reported.<ref name="Asakawa"> |
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{{Unbulleted list citebundle |
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|{{*}} {{cite journal |last1=Asakawa |first1=Y. |last2=Taira |first2=Z. |last3=Takemoto |first3=T. |last4=Ishida |first4=T. |last5=Kido |first5=M. |last6=Ichikawa |first6=Y. |title=X-Ray Crystal Structure Analysis of 14-Hydroxycaryophyllene Oxide, a New Metabolite of (—)-Caryophyllene, in Rabbits |journal=Journal of Pharmaceutical Sciences |date=June 1981 |volume=70 |issue=6 |pages=710–711 |doi=10.1002/jps.2600700642 |language=en | pmid=7252830 | s2cid=38358882}} |
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|{{*}} {{cite journal | last1=Adams | first1=T.B. | last2=Gavin | first2=C. Lucas | last3=McGowen | first3=M.M. | last4=Waddell | first4=W.J. | last5=Cohen | first5=S.M. | last6=Feron | first6=V.J. | last7=Marnett | first7=L.J. | last8=Munro | first8=I.C. | last9=Portoghese | first9=P.S. | last10=Rietjens | first10=I.M.C.M. | last11=Smith | first11=R.L. | title=The FEMA GRAS assessment of aliphatic and aromatic terpene hydrocarbons used as flavor ingredients | journal=] | publisher=] | volume=49 | issue=10 | year=2011 | issn=0278-6915 | doi=10.1016/j.fct.2011.06.011 | pages=2471–2494 | s2cid=207734236 | pmid=21726592}} |
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|{{*}} {{cite journal | year=2005 | volume=2 | issue=5 | last=Ishida | first=Takashi | publisher=] (Swiss Chemical Society) | pages=569–590 | s2cid=22213646 | pmid=17192005 | doi=10.1002/cbdv.200590038 | journal= Chemistry & Biodiversity | issn=1612-1872 | title=Biotransformation of Terpenoids by Mammals, Microorganisms, and Plant-Cultured Cells}} |
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</ref> |
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The ] of caryophyllene progresses through (−)-caryophyllene oxide (C<sub>15</sub>H<sub>24</sub>O) since the latter compound also afforded 14-hydroxycaryophyllene (C<sub>15</sub>H<sub>24</sub>O) as a ].<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/1742210#section=Top|title=Caryophyllene oxide – C<sub>15</sub>H<sub>24</sub>O |website=]|access-date=September 8, 2016}}</ref> |
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:Caryophyllene (C<sub>15</sub>H<sub>24</sub>) → caryophyllene oxide (C<sub>15</sub>H<sub>24</sub>O) → 14-hydroxycaryophyllene (C<sub>15</sub>H<sub>24</sub>O) → 14-hydroxycaryophyllene oxide (]<sub>15</sub>]<sub>24</sub>]<sub>2</sub>). |
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Caryophyllene oxide,<ref>{{cite journal |last1=Yang |first1=Depo |last2=Michel |first2=Laura |last3=Chaumont |first3=Jean-Pierre |last4=Millet-Clerc |first4=Joëlle |title=Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis |journal=Mycopathologia |date=1999 |volume=148 |issue=2 |pages=79–82 |doi=10.1023/a:1007178924408 |pmid=11189747 |s2cid=24242933 }}</ref> in which the ] group of caryophyllene has become an ], is the component responsible for cannabis identification by ]<ref>{{cite journal |last1=Russo |first1=Ethan B |title=Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects: Phytocannabinoid-terpenoid entourage effects |journal=British Journal of Pharmacology |date=August 2011 |volume=163 |issue=7 |pages=1344–1364 |doi=10.1111/j.1476-5381.2011.01238.x |pmid=21749363 |pmc=3165946 }}</ref><ref>{{cite journal | last1 = Stahl | first1 = E. | last2 = Kunde | first2 = R. | year = 1973 | title = Die Leitsubstanzen der Haschisch-Suchhunde | trans-title = The tracing substances of hashish search dogs | language = de | journal = Kriminalistik | volume = 27 | pages = 385–389 }}</ref> and is also an approved food additive, often as flavoring.<ref name="accessdata.fda.gov"/> Caryophyllene oxide may have negligible cannabinoid activity.<ref>{{cite journal |last1=Wiley |first1=Jenny L. |last2=Marusich |first2=Julie A. |last3=Blough |first3=Bruce E. |last4=Namjoshi |first4=Ojas |last5=Brackeen |first5=Marcus |last6=Akinfiresoye |first6=Luli R. |last7=Walker |first7=Teneille D. |last8=Prioleau |first8=Cassandra |last9=Barrus |first9=Daniel G. |last10=Gamage |first10=Thomas F. |title=Evaluation of cannabimimetic effects of selected minor cannabinoids and Terpenoids in mice |journal=Progress in Neuro-Psychopharmacology and Biological Psychiatry |date=June 2024 |volume=132 |pages=110984 |doi=10.1016/j.pnpbp.2024.110984 |pmid=38417478 |pmc=11015967 |pmc-embargo-date=June 8, 2025 |s2cid=267941924 }}</ref> |
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==Natural sources== |
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==Natural sources== |
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The approximate quantity of caryophyllene in the ] of each source is given in square brackets (''''): |
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The approximate quantity of caryophyllene in the ] of each source is given in square brackets (''''): |
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*], ], ] ('']'')<ref name="pmid18574142"/> ]]<ref>{{cite web |first=Vito |last=Mediavilla |coauthors=Simon Steinemann |url=http://www.internationalhempassociation.org/jiha/jiha4208.html |title=Essential oil of ''Cannabis sativa'' L. strains |publisher=International Hemp Association |accessdate=11 July 2008}}</ref> |
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*] ('']'') ]]<ref>{{cite web |first1=V. |last1=Mediavilla |first2=S. |last2=Steinemann |url=http://www.internationalhempassociation.org/jiha/jiha4208.html |title=Essential oil of ''Cannabis sativa'' L. strains |publisher=International Hemp Association |access-date=11 July 2008}}</ref> |
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*] ('']'') <ref name="pmid16390196">{{cite journal |author=Singh G, Marimuthu P, de Heluani CS, Catalan CA |title=Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components |journal=J. Agric. Food Chem. |volume=54 |issue=1 |pages=174–81 |year=2006 |month=January |pmid=16390196 |doi=10.1021/jf0518610 |url=}}</ref> |
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*] (''Carum nigrum'') <ref name="pmid16390196">{{cite journal |last1=Singh |first1=G. |last2=Marimuthu |first2=P. |last3=De Heluani |first3=C. S. |last4=Catalan |first4=C. A. |title=Antioxidant and biocidal activities of ''Carum nigrum'' (seed) essential oil, oleoresin, and their selected components |journal=Journal of Agricultural and Food Chemistry |volume=54 |issue=1 |pages=174–181 |date=January 2006 |pmid=16390196 |doi=10.1021/jf0518610 |bibcode=2006JAFC...54..174S |hdl=11336/99544 |hdl-access=free }}</ref> |
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*]s ('']'')<ref name="pmid11482764"/> ]]<ref name="issn19302126">{{cite journal |last1=Alma |first1=M. Hakkı |last2=Ertaş |first2=Murat |last3=Nitz |first3=Siegfrie |last4=Kollmannsberger |first4=Hubert |editor1-first=Lucian A. |editor1-last=Lucia |editor2-first=Martin A. |editor2-last=Hubbe |year=2007 |month=May |title=Chemical composition and content of essential oil from the bud of cultivated Turkish clove |journal=BioResources |volume=2 |issue=2 |pages=265–269 |publisher=North Carolina State University |location=Raleigh, North Carolina, USA |issn=1930-2126 |url=http://www.ncsu.edu/bioresources/BioRes_02/BioRes_02_2_265_269_Alma_ENK_CloveOil_Turkish.pdf |format=PDF |accessdate=September 6, 2010 |quote=The results showed that the essential oils mainly contained about 3.56% ''β''-Caryophyllene}}</ref> |
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*]s (''Syzygium aromaticum'') ]]<ref>{{cite journal |last1=Alma |first1=M. Hakki |last2=Ertaş |first2=Murat |last3=Nitz |first3=Siegfrie |last4=Kollmannsberger |first4=Hubert |title=Chemical composition and content of essential oil from the bud of cultivated Turkish clove (Syzygium aromaticum L.) |journal=BioResources |date=23 May 2007 |volume=2 |issue=2 |pages=265–269 |doi=10.15376/biores.2.2.265-269 |doi-access=free }}</ref> |
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*] ('']'')<ref name="pmid18775972">{{cite journal |author=Wang G, Tian L, Aziz N, ''et al.'' |title=Terpene Biosynthesis in Glandular Trichomes of Hop |journal=Plant Physiol. |volume=148 |issue=3 |pages=1254–66 |year=2008 |month=November |pmid=18775972 |pmc=2577278 |doi=10.1104/pp.108.125187 |url=}}</ref> <ref name="issn02357216">{{cite journal|last1=Bernotienë|first1=Genovaitë|last2=Nivinskienë|first2=Ona|last3=Butkienë|first3=Rita|last4=Mockutë|first4=Danutë|year=2004|title=Chemical composition of essential oils of hops (Humulus lupulus L.) growing wild in Auktaitija|journal=Chemija|volume=4|series=2|pages=31–36|publisher=Lithuanian Academy of Sciences|location=Vilnius, Lithuania|issn=0235-7216|url=http://www.elibrary.lt/resursai/LMA/Chemija/C-31.pdf|accessdate=September 6, 2010}}</ref> |
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*] ('']'')<ref>{{cite journal |last1=Wang |first1=Guodong |last2=Tian |first2=Li |last3=Aziz |first3=Naveed |last4=Broun |first4=Pierre |last5=Dai |first5=Xinbin |last6=He |first6=Ji |last7=King |first7=Andrew |last8=Zhao |first8=Patrick X. |last9=Dixon |first9=Richard A. |title=Terpene Biosynthesis in Glandular Trichomes of Hop |journal=Plant Physiology |date=6 November 2008 |volume=148 |issue=3 |pages=1254–1266 |doi=10.1104/pp.108.125187 |pmid=18775972 |pmc=2577278 }}</ref> <ref name="issn02357216">{{cite journal|last1=Bernotienë|first1=G.|last2=Nivinskienë|first2=O.|last3=Butkienë|first3=R.|last4=Mockutë|first4=D.|year=2004|title=Chemical composition of essential oils of hops (''Humulus lupulus'' L.) growing wild in Auktaitija|journal=Chemija|volume=4|series=2|pages=31–36|url=http://www.elibrary.lt/resursai/LMA/Chemija/C-31.pdf|access-date=September 6, 2010|archive-date=March 7, 2023|archive-url=https://web.archive.org/web/20230307193722/http://www.elibrary.lt/resursai/LMA/Chemija/C-31.pdf|url-status=dead}}</ref> |
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*] ('']'' spp.)<ref name="pmid18095647">{{cite journal |author=Zheljazkov VD, Cantrell CL, Tekwani B, Khan SI |title=Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting |journal=J. Agric. Food Chem. |volume=56 |issue=2 |pages=380–5 |year=2008 |month=January |pmid=18095647 |doi=10.1021/jf0725629 |url=}}</ref> ]''; 4.0–19.8% '']'']<ref name="issn14246376">{{cite journal |last1=Silva |first1=Maria Goretti de Vasconcelos |last2=Matos |first2=Francisco José de Abreu |last3=Lopes |first3=Paulo Roberto Oliveira |last4=Silva |first4=Fábio Oliveira |last5=Holanda |first5=Márcio Tavares |editor1-first=Gordon M. |editor1-last=Cragg |editor2-first=Vanderlan S. |editor2-last=Bolzani |editor3-first=G. S. R. Subba |editor3-last=Rao |date=August 2, 2004 |title=Composition of essential oils from three ''Ocimum'' species obtained by steam and microwave distillation and supercritical CO<sub>2</sub> extraction |journal=Arkivoc |volume=2004 |issue=vi |pages=66–71 |publisher=ARKAT USA, Inc. |issn=1424-6376 |url=http://www.arkat-usa.org/get-file/19788/ |format=PDF |accessdate=September 6, 2010}}</ref> |
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*] ('']'' spp.)<ref name="pmid18095647">{{cite journal |last1=Zheljazkov |first1=V. D. |last2=Cantrell |first2=C. L. |last3=Tekwani |first3=B. |last4=Khan |first4=S. I. |title=Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting |journal=Journal of Agricultural and Food Chemistry |volume=56 |issue=2 |pages=380–5 |date=January 2008 |pmid=18095647 |doi=10.1021/jf0725629 |bibcode=2008JAFC...56..380Z }}</ref> ]''; 4.0–19.8% '']'']<ref name="issn14246376">{{cite journal |last1=Vasconcelos Silva |first1=M. G. |last2=Abreu Matos |first2=F. J. |last3=Oliveira Lopes |first3=P. R. |last4=Oliveira Silva |first4=F. |last5=Tavares Holanda |first5=M. |editor1-first=G. M. |editor1-last=Cragg |editor2-first=V. S. |editor2-last=Bolzani|editor-link2=Vanderlan da Silva Bolzani |editor3-first=G. S. R. S. |editor3-last=Rao |date=August 2, 2004 |title=Composition of essential oils from three ''Ocimum'' species obtained by steam and microwave distillation and supercritical CO<sub>2</sub> extraction |journal=Arkivoc |volume=2004 |issue=6 |pages=66–71 |doi=10.3998/ark.5550190.0005.609 |doi-access=free |hdl=2027/spo.5550190.0005.609 |hdl-access=free }}</ref> |
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*] ('']'')<ref name="pmid17268981">{{cite journal |author=Harvala C, Menounos P, Argyriadou N |title=Essential Oil from Origanum dictamnus |journal=Planta Med. |volume=53 |issue=1 |pages=107–9 |year=1987 |month=February |pmid=17268981 |doi=10.1055/s-2006-962640 |url=}}</ref> <ref name="issn15403580">{{cite journal |last1=Calvo-Irabien |first1=L. M. |last2=Yam-Puc |first2=J. A. |last3=Dzib |first3=G. |last4=Escalante-Erosa |first4=F. |last5=Peña-Rodriguez |first5=L. M. |year=2009 |month=July |title=Effect of Postharvest Drying on the Composition of Mexican Oregano (''Lippia graveolens'') Essential Oil |journal=Journal of Herbs, Spices & Medicinal Plants |volume=15 |issue=3 |pages=281–287 |publisher=Taylor & Francis |location=London, UK |issn=1540-3580 |doi=10.1080/10496470903379001}}</ref> |
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*] (''Origanum vulgare'')<ref name="pmid17268981">{{cite journal |vauthors=Harvala C, Menounos P, Argyriadou N |title=Essential oil from ''Origanum dictamnus'' |journal=Planta Medica |volume=53 |issue=1 |pages=107–109 |date=February 1987 |pmid=17268981 |doi=10.1055/s-2006-962640 |s2cid=260278580 }}</ref> <ref name="issn15403580">{{cite journal |last1=Calvo Irabién |first1=L. M. |last2=Yam-Puc |first2=J. A. |last3=Dzib |first3=G. |last4=Escalante Erosa |first4=F. |last5=Peña Rodríguez |first5=L. M. |date=July 2009 |title=Effect of postharvest drying on the composition of Mexican oregano (''Lippia graveolens'') essential oil |journal=Journal of Herbs, Spices & Medicinal Plants |volume=15 |issue=3 |pages=281–287 |doi=10.1080/10496470903379001 |s2cid=86208062 }}</ref><ref>{{cite journal | pmid = 11336262 | volume=57 | issue=1 | title=The essential oil of ''Origanum vulgare'' L. ssp. ''vulgare'' growing wild in Vilnius district (Lithuania) | date=May 2001 | journal=Phytochemistry | pages=65–69 | doi=10.1016/s0031-9422(00)00474-x| last1=Mockutė | first1=D. | last2=Bernotienė | first2=G. | last3=Judžentienė | first3=A. | bibcode=2001PChem..57...65M }}</ref> |
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*] (''Piper nigrum'') <ref name="pmid12462618"/> |
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*] ('']'') <ref name="pmid12462618">{{cite journal |author=Jirovetz L, Buchbauer G, Ngassoum MB, Geissler M |title=Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry |journal=J Chromatogr A |volume=976 |issue=1–2 |pages=265–75 |year=2002 |month=November |pmid=12462618 |doi= 10.1016/S0021-9673(02)00376-X|url=}}</ref> |
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*] (''Lavandula angustifolia'') ]]<ref>{{cite journal | last1 = Prashar | first1 = A. | last2 = Locke | first2 = I. C. | last3 = Evans | first3 = C. S. | year = 2004 | title = Cytotoxicity of lavender oil and its major components to human skin cells | journal = Cell Proliferation | volume = 37 | issue = 3| pages = 221–229 | doi=10.1111/j.1365-2184.2004.00307.x | pmid=15144499| pmc = 6496511 }}</ref><ref>{{cite journal|last1=Umezu|first1=T.|last2=Nagano|first2=K.|last3=Ito|first3=H.|last4=Kosakai|first4=K.|last5=Sakaniwa|first5=M.|last6=Morita|first6=M.|title=Anticonflict effects of lavender oil and identification of its active constituents|journal=Pharmacology Biochemistry and Behavior|date=December 2006|volume=85|issue=4|pages=713–721|doi=10.1016/j.pbb.2006.10.026|pmid=17173962|s2cid=21779233}}</ref> |
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*] ('']'') <ref name="pmid12462618"/> |
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*] ('']'')<ref name="pmid18670820">{{cite journal |author=Ormeño E, Baldy V, Ballini C, Fernandez C |title=Production and diversity of volatile terpenes from plants on calcareous and siliceous soils: effect of soil nutrients |journal=J. Chem. Ecol. |volume=34 |issue=9 |pages=1219–29 |year=2008 |month=September |pmid=18670820 |doi=10.1007/s10886-008-9515-2 |url=}}</ref> <ref name="issn19904053">{{cite journal |last1=Jamshidi |first1=R. |last2=Afzali |first2=Z. |last3=Afzali |first3=D. |year=2009 |month=February |title=Chemical Composition of Hydrodistillation Essential Oil of Rosemary in Different Origins in Iran and Comparison with Other Countries |journal=American-Eurasian Journal of Agricultural & Environmental Sciences |volume=5 |issue=1 |pages=78–81 |publisher=IDOSI Publications |location=Pakistan |issn=1990-4053 |url=http://www.idosi.org/aejaes/jaes5(1)/13.pdf |format=PDF |accessdate=September 6, 2010}}</ref> |
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*] (''Rosmarinus officinalis'')<ref name="pmid18670820">{{cite journal |last1=Ormeño |first1=E. |last2=Baldy |first2=V. |last3=Ballini |first3=C. |last4=Fernández |first4=C. |title=Production and diversity of volatile terpenes from plants on calcareous and siliceous soils: effect of soil nutrients |journal=Journal of Chemical Ecology |volume=34 |issue=9 |pages=1219–1229 |date=September 2008 |pmid=18670820 |doi=10.1007/s10886-008-9515-2 |bibcode=2008JCEco..34.1219O |s2cid=28717342 }}</ref> {{citation needed|date=May 2019}} |
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*] ('']'') <ref name="Cinnamomum zeylanicum">{{cite journal |doi=10.1002/jsfa.1277 |title=Volatile constituents of essential oils isolated from different parts of cinnamon (''Cinnamomum zeylanicum'' Blume) |year=2003 |author=Kaul PN, Bhattacharya AK, Rao BRR, ''et al.'' |journal=Journal of the Science of Food and Agriculture |volume=83 |issue=1 |pages=53–55}}</ref> |
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*] (''Cinnamomum verum'') <ref>{{cite journal |last1=Kaul |first1=Pran N |last2=Bhattacharya |first2=Arun K |last3=Rajeswara Rao |first3=Bhaskaruni R |last4=Syamasundar |first4=Kodakandla V |last5=Ramesh |first5=Srinivasaiyer |title=Volatile constituents of essential oils isolated from different parts of cinnamon (''Cinnamomum zeylanicum'' Blume) |journal=Journal of the Science of Food and Agriculture |date=1 January 2003 |volume=83 |issue=1 |pages=53–55 |doi=10.1002/jsfa.1277 |bibcode=2003JSFA...83...53K }}</ref> |
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*] ('']'') <ref name=eocs>{{cite journal |doi=10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F |title=Essential oil constituents of the spice ''Cinnamomum tamala'' (Ham.) Nees & Eberm |year=2000 |author=Ahmed A, Choudhary MI, Farooq A, ''et al.'' |journal=Flavour and Fragrance Journal |volume=15 |issue=6 |pages=388–390}}</ref> |
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*] ('']'') <ref>{{cite journal |last1=Ahmed |first1=Aftab |last2=Choudhary |first2=M. Iqbal |last3=Farooq |first3=Afgan |last4=Demirci |first4=Betül |last5=Demirci |first5=Fatih |last6=Başer |first6=K. Hüsnü Can |title=Essential oil constituents of the spice ''Cinnamomum tamala'' (Ham.) Nees & Eberm |journal=Flavour and Fragrance Journal |date=2000 |volume=15 |issue=6 |pages=388–390 |doi=10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F |doi-access=free }}</ref> |
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*] (''Cananga odorata'') |
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*] oil ('']'')<ref>{{cite journal |last1=Leandro |first1=Lidiam Maia |last2=de Sousa Vargas |first2=Fabiano |last3=Barbosa |first3=Paula Cristina Souza |last4=Neves |first4=Jamilly Kelly Oliveira |last5=da Silva |first5=José Alexsandro |last6=da Veiga-Junior |first6=Valdir Florêncio |title=Chemistry and Biological Activities of Terpenoids from Copaiba (Copaifera spp.) Oleoresins |journal=Molecules |date=30 March 2012 |volume=17 |issue=4 |pages=3866–3889 |doi=10.3390/molecules17043866 |pmid=22466849 |pmc=6269112 |doi-access=free }}</ref><ref>{{cite journal |last1=Sousa |first1=João Paulo B. |last2=Brancalion |first2=Ana P.S. |last3=Souza |first3=Ariana B. |last4=Turatti |first4=Izabel C.C. |last5=Ambrósio |first5=Sérgio R. |last6=Furtado |first6=Niege A.J.C. |last7=Lopes |first7=Norberto P. |last8=Bastos |first8=Jairo K. |title=Validation of a gas chromatographic method to quantify sesquiterpenes in copaiba oils |journal=Journal of Pharmaceutical and Biomedical Analysis |date=March 2011 |volume=54 |issue=4 |pages=653–659 |doi=10.1016/j.jpba.2010.10.006 |pmid=21095089 |doi-access=free }}</ref> |
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=== Biosynthesis === |
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Caryophyllene is a common ] among plant species. It is biosynthesized from the common ] precursors ] (DMAPP) and ] (IPP). First, single units of DMAPP and IPP are reacted via an ]-type reaction with the loss of ], catalyzed by the enzyme ], to form ] (GPP). This further reacts with a second unit of IPP, also via an ] catalyzed by the enzyme ], to form ] (FPP). Finally, FPP undergoes ] enzyme-catalyzed intramolecular cyclization to form caryophyllene.<ref>{{cite journal |last1=Yang |first1=Jianming |last2=Li |first2=Zhengfeng |last3=Guo |first3=Lizhong |last4=Du |first4=Juan |last5=Bae |first5=Hyeun-Jong |title=Biosynthesis of β-caryophyllene, a novel terpene-based high-density biofuel precursor, using engineered ''Escherichia coli'' |journal=Renewable Energy |date=December 2016 |volume=99 |pages=216–223 |doi=10.1016/j.renene.2016.06.061 |bibcode=2016REne...99..216Y }}</ref> |
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==Compendial status== |
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==Compendial status== |
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* Food Chemical Codex <ref name=rffs>{{cite web |
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* ]<ref name=rffs>{{cite web |
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|title=Revisions to FCC, First Supplement |
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|url=http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html |
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}}</ref><sup>,</sup> <ref name=cs>{{cite web |
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| archive-url = https://web.archive.org/web/20110422122647/http://www.tga.gov.au/docs/pdf/aan/aanchem.pdf |
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==Further reading== |
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* {{cite journal |last1=Ghelardini |first1=C. |last2=Galeotti |first2=N. |last3=Di Cesare Mannelli |first3=L. |last4=Mazzanti |first4=G. |last5=Bartolini |first5=A. |title=Local anaesthetic activity of beta-caryophyllene |journal=Farmaco |volume=56 |issue=5–7 |pages=387–389 |year=2001 |pmid=11482764 |doi= 10.1016/S0014-827X(01)01092-8|hdl=2158/397975 |hdl-access=free }} |
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==Notes and references== |
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==Notes and references== |
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{{Reflist}} |
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{{Reflist|2}} |
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{{Cannabinoids}} |
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==External links== |
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{{Cannabinoidergics}} |
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*, Aaron Rowe, '']'', June 29, 2008 |
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{{Authority control}} |
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