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词条 Caryophyllene
释义

  1. Metabolism and derivatives

  2. Natural sources

  3. Compendial status

  4. Notes and references

{{chembox
| Watchedfields = changed
| verifiedrevid = 460021442
| Name = Caryophyllene
| ImageFile =
| ImageFile1 = Beta-Caryophyllen.svg
| ImageName = beta-caryophyllene
| PIN = (1R,4E,9S)-4,11,11-Trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
| SystematicName =
| OtherNames = β-Caryophyllene
trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
| IUPACName =
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444848
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 445740
| PubChem = 5281515
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BHW853AU9H
| InChI = 1/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1
| InChIKey = NPNUFJAVOOONJE-GFUGXAQUBC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NPNUFJAVOOONJE-GFUGXAQUSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 87-44-5
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 10357
| SMILES = C1(=C)\\CC/C=C(/CC[C@@H]2[C@@H]1CC2(C)C)C
}}
| Section2 = {{Chembox Properties
| C=15
| H=24
| Density = 0.9052 g/cm3 (17 °C)[1]
| MeltingPt =
| BoilingPtC = 262 - 264
| BoilingPt_ref= [2]
| Section3 =
| Section4 =
| Section5 =
| Section6 =
}}

Caryophyllene {{IPAc-en|ˌ|k|ær|i|oʊ-|f|ɪ|ˈ|l|iː|n}}, or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves),[3] the essential oil of Cannabis sativa, rosemary,[4] and hops.[4] It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.[5]

Caryophyllene is one of the chemical compounds that contributes to the aroma of black pepper.[6]

Metabolism and derivatives

14-Hydroxycaryophyllene oxide (C15H24O2) was isolated from the urine of rabbits treated with (-)-caryophyllene (C15H24). The x-ray crystal structure of 14-hydroxycaryophyllene (as its acetate derivative) has been reported.

The metabolism of caryophyllene progresses through (-)-caryophyllene oxide (C15H24O) since the latter compound also afforded 14-hydroxycaryophyllene (C15H24O) as a metabolite.[7]

Caryophyllene (C15H24) → caryophyllene oxide (C15H24O) → 14-hydroxycaryophyllene (C15H24O) → 14-hydroxycaryophyllene oxide (C15H24O2).

Caryophyllene oxide,[8] in which the olefin of caryophyllene has become an epoxide, is the component responsible for cannabis identification by drug-sniffing dogs[9][10] and is also an approved food flavoring.

Natural sources

The approximate quantity of caryophyllene in the essential oil of each source is given in square brackets ('):

  • Cannabis, hemp, marijuana (Cannabis sativa) [3.8–37.5% of cannabis flower essential oil][11]
  • Black caraway (Carum nigrum) [7.8%][12]
  • Cloves (Syzygium aromaticum)[3] [1.7–19,5% of clove bud essential oil][13]
  • Hops (Humulus lupulus)[14] [5.1–14.5%][15]
  • Basil (Ocimum spp.)[16] [5.3–10.5% O. gratissimum; 4.0–19.8% O. micranthum][17]
  • Oregano (Origanum vulgare)[18] [4.9–15.7%][19][20]
  • Black pepper (Piper nigrum) [7.29%][6]
  • Lavender (Lavandula angustifolia) [4.62–7.55% of lavender oil][21][22]
  • Rosemary (Rosmarinus officinalis)[23] [0.1–8.3%][24]
  • True cinnamon (Cinnamomum zeylanicum) [6.9–11.1%][25]
  • Malabathrum (Cinnamomum tamala) [25.3%][26]
  • Ylang-ylang (Cananga odorata) [3.1–10.7%]
  • Copaiba oil (Copaifera spp.)[27][28]

Compendial status

  • Food Chemicals Codex[29][30]

Notes and references

1. ^SciFinder Record, CAS Registry Number 87-44-5
2. ^{{cite journal | author = Baker, Richard 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}}
3. ^1 {{cite journal |vauthors=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=}}
4. ^Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. Accessed July 21, 2010.
5. ^{{cite journal |vauthors=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}}
6. ^1 {{cite journal |vauthors=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 |date=November 2002 |pmid=12462618 |doi= 10.1016/S0021-9673(02)00376-X|url=}}
7. ^{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/1742210#section=Top|title=Caryophyllene oxide {{!}} C15H24O - PubChem|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov|access-date=2016-09-08}}
8. ^{{Cite journal|last=Yang|first=D.|last2=Michel|first2=L.|last3=Chaumont|first3=J. P.|last4=Millet-Clerc|first4=J.|date=1999-11-01|title=Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis|journal=Mycopathologia|volume=148|issue=2|pages=79–82|issn=0301-486X|pmid=11189747|doi=10.1023/A:1007178924408}}
9. ^{{cite journal | last1 = Russo | first1 = Ethan | year = 2011 | title = Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects | journal = Br J Pharmacol | volume = 163 | issue = 7| pages = 1344–1364 | pmc=3165946 | pmid=21749363 | doi=10.1111/j.1476-5381.2011.01238.x}}
10. ^{{cite journal | last1 = Stahl | first1 = E | last2 = Kunde | first2 = R | year = 1973 | title = Die Leitsubstanzen der Haschisch-Suchhunde | url = | journal = Kriminalistik: Z Gesamte Kriminal Wiss Prax. | volume = 27 | issue = | pages = 385–389 }}
11. ^{{cite web |first=Vito |last=Mediavilla |author2=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}}
12. ^{{cite journal |vauthors=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 |date=January 2006 |pmid=16390196 |doi=10.1021/jf0518610 |url=}}
13. ^{{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 |date=May 2007 |title=Chemical composition and content of essential oil from the bud of cultivated Turkish clove |journal=BioResources |volume=2 |issue=2 |pages=265–269 |issn=1930-2126 |url=http://www.ncsu.edu/bioresources/BioRes_02/BioRes_02_2_265_269_Alma_ENK_CloveOil_Turkish.pdf |accessdate=September 6, 2010 |quote=The results showed that the essential oils mainly contained about [...] 3.56% β-Caryophyllene}}
14. ^{{cite journal |vauthors=Wang G, Tian L, Aziz N |title=Terpene Biosynthesis in Glandular Trichomes of Hop |journal=Plant Physiol. |volume=148 |issue=3 |pages=1254–66 |date=November 2008 |pmid=18775972 |pmc=2577278 |doi=10.1104/pp.108.125187 |url=|display-authors=etal}}
15. ^{{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|issn=0235-7216|url=http://www.elibrary.lt/resursai/LMA/Chemija/C-31.pdf|accessdate=September 6, 2010}}
16. ^{{cite journal |vauthors=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 |date=January 2008 |pmid=18095647 |doi=10.1021/jf0725629 |url=}}
17. ^{{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 CO2 extraction |journal=Arkivoc |volume=2004 |issue=vi |pages=66–71 |issn=1424-6376 |url=http://www.arkat-usa.org/get-file/19788/ |format=PDF |accessdate=September 6, 2010 |doi=10.3998/ark.5550190.0005.609}}
18. ^{{cite journal |vauthors=Harvala C, Menounos P, Argyriadou N |title=Essential Oil from Origanum dictamnus |journal=Planta Med. |volume=53 |issue=1 |pages=107–9 |date=February 1987 |pmid=17268981 |doi=10.1055/s-2006-962640 |url=}}
19. ^{{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. |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 |issn=1540-3580 |doi=10.1080/10496470903379001}}
20. ^{{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=65–9 | doi=10.1016/s0031-9422(00)00474-x| author1=Mockute | first1=D | last2=Bernotiene | first2=G | last3=Judzentiene | first3=A }}
21. ^{{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 | url = | journal = Cell Proliferation | volume = 37 | issue = 3| pages = 221–229 | doi=10.1111/j.1365-2184.2004.00307.x | pmid=15144499}}
22. ^{{cite journal|last1=Umezu|first1=Toyoshi|last2=Nagano|first2=Kimiyo|last3=Ito|first3=Hiroyasu|last4=Kosakai|first4=Kiyomi|last5=Sakaniwa|first5=Misao|last6=Morita|first6=Masatoshi|title=Anticonflict effects of lavender oil and identification of its active constituents|journal=Pharmacology Biochemistry and Behavior|date=1 December 2006|volume=85|issue=4|pages=713–721|doi=10.1016/j.pbb.2006.10.026|pmid=17173962|url=http://www.sciencedirect.com/science/article/pii/S0091305706003686|accessdate=21 February 2017}}
23. ^1 {{cite journal |vauthors=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 |date=September 2008 |pmid=18670820 |doi=10.1007/s10886-008-9515-2 |url=}}
24. ^{{cite journal |last1=Jamshidi |first1=R. |last2=Afzali |first2=Z. |last3=Afzali |first3=D. |date=February 2009 |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 |issn=1990-4053 |url=http://www.idosi.org/aejaes/jaes5(1)/13.pdf |accessdate=September 6, 2010}}
25. ^{{cite journal |doi=10.1002/jsfa.1277 |title=Volatile constituents of essential oils isolated from different parts of cinnamon (Cinnamomum zeylanicum Blume) |year=2003 |vauthors=Kaul PN, Bhattacharya AK, Rao BR |journal=Journal of the Science of Food and Agriculture |volume=83 |issue=1 |pages=53–55|display-authors=etal}}
26. ^{{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 |vauthors=Ahmed A, Choudhary MI, Farooq A |journal=Flavour and Fragrance Journal |volume=15 |issue=6 |pages=388–390|display-authors=etal}}
27. ^{{cite journal |pmid=22466849 | doi=10.3390/molecules17043866 | volume=17 | issue=4 | title=Chemistry and biological activities of terpenoids from copaiba (Copaifera spp.) oleoresins | year=2012 | journal=Molecules | pages=3866–89| author1=Leandro | first1=L. M. | last2=Vargas Fde | first2=S | last3=Barbosa | first3=P. C. | last4=Neves | first4=J. K. | last5=Da Silva | first5=J. A. | last6=Da Veiga-Junior | first6=V. F. }}
28. ^{{cite journal |pmid=21095089 | doi=10.1016/j.jpba.2010.10.006 | volume=54 | issue=4 | title=Validation of a gas chromatographic method to quantify sesquiterpenes in copaiba oils | date=Mar 2011 | journal=J Pharm Biomed Anal | pages=653–9| author1=Sousa | first1=J. P. | last2=Brancalion | first2=A. P. | last3=Souza | first3=A. B. | last4=Turatti | first4=I. C. | last5=Ambrósio | first5=S. R. | last6=Furtado | first6=N. A. | last7=Lopes | first7=N. P. | last8=Bastos | first8=J. K. }}
29. ^{{cite web |last=The United States Pharmacopeial Convention |title=Revisions to FCC, First Supplement |website= |url=http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html |doi= |accessdate=29 June 2009 |deadurl=yes |archiveurl=https://web.archive.org/web/20100705122159/http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html |archivedate=5 July 2010 |df= }}
30. ^{{cite web | author = Therapeutic Goods Administration | title = Chemical substances | website = | url = http://www.tga.gov.au/docs/pdf/aan/aanchem.pdf | format = | doi = | accessdate = 29 June 2009 }}
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