Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 12:16, 25 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit		Latest revision as of 05:10, 31 October 2024 edit undoMdewman6 (talk | contribs)Extended confirmed users, Page movers, New page reviewers, Pending changes reviewers, Rollbackers21,716 editsm remove "the"
(196 intermediate revisions by more than 100 users not shown)
Line 1:		Line 1:
			{{this|β-myrcene|its isomer|α-Myrcene}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 402501399
			| Watchedfields = changed
	| Reference=<ref>'']'', 11th Edition, '''6243'''</ref>
			| verifiedrevid = 415853613
	| Name = Myrcene
			| Reference =<ref>'']'', 11th Edition, '''6243'''</ref>
	| ImageFile = Myrcene beta straight acsv.svg
	| ImageSize = 220px		| Name = Myrcene
			| ImageFile = Myrcene beta straight acsv.svg
	| ImageName = Beta-myrcene, skeletal formula
			| ImageSize = 220px
	| ImageFile1 = Myrcene-3D-balls.png
			| ImageName = Beta-myrcene, skeletal formula
	| ImageSize1 = 230px
	| ImageName1 = Beta-myrcene, ball-and-stick model		| ImageFile1 = Beta-Myrcene molecule ball.png
			| ImageSize1 = 230px
	| IUPACName = 7-Methyl-3-methylene-1,6-octadiene
			| ImageName1 = Ball-and-stick model of the beta-myrcene molecule
	| Section1 = {{Chembox Identifiers
			| PIN = 7-Methyl-3-methylideneocta-1,6-diene
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|Section1={{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 28993		| ChemSpiderID = 28993
	| PubChem = 31253		| PubChem = 31253
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C06074		| KEGG = C06074
	| InChI = 1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3		| InChI = 1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3
	| InChIKey = UAHWPYUMFXYFJY-UHFFFAOYAT		| InChIKey = UAHWPYUMFXYFJY-UHFFFAOYAT
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 455491		| ChEMBL = 455491
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 23:		Line 28:
	| StdInChIKey = UAHWPYUMFXYFJY-UHFFFAOYSA-N		| StdInChIKey = UAHWPYUMFXYFJY-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 123-35-3		| CASNo = 123-35-3
			| UNII_Ref = {{fdacite|correct|FDA}}
	| SMILES = CC(=CCCC(=C)C=C)C
			| UNII = 3M39CZS25B
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 17221
			| SMILES = CC(=CCCC(=C)C=C)C
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=10|H=16		| C=10 | H=16
	| Density = 0.794 g/cm<sup>3</sup>		| Density = 0.794 g/cm<sup>3</sup>
	| MeltingPt = < -10 °C		| MeltingPt= <
			| MeltingPtC = -10
	| BoilingPt = 166-168 °C<ref name=Ullmann/><!-- Index of refraction for myrcene 1.4697 according to Ullmann's-->
			| BoilingPtC = 166 to 168
			| BoilingPt_ref = <ref name=Ullmann/><!-- Index of refraction for myrcene 1.4697 according to Ullmann's-->
	}}
			}}
	}}		}}
			'''Myrcene''', or '''β-myrcene''', is a ]. A colorless oil, it occurs widely in ]s. It is produced mainly semi-synthetically from '']'', from which it gets its name. It is an intermediate in the production of several fragrances.<ref name=Behr>{{cite journal |author1=Behr, A. |author2=Johnen, L.| title = Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review | journal = ChemSusChem | year = 2009 | volume = 2 | issue = 12 | pages = 1072–1095 | doi = 10.1002/cssc.200900186 | pmid=20013989|bibcode=2009ChSCh...2.1072B }}</ref> An less-common ]ic form, having one of the three ] units in a different position, is ].
	'''Myrcene''', or β-myrcene, is an ] natural ]. It is classified as a ], but more precisely as a ]. Terpenes are ]s of ] and myrcene is one of the most important. It is a component of the ] of the several plants including ], ], ], and ].<ref name=csoc>{{cite journal
	| last = Chyau
	| first = Charng-Cherng ''et al.''
	| authorlink =
	| coauthors =
	| title = Characteristics of the Steam-Distilled Oil and Carbon Dioxide Extract of Zanthoxylum simulans Fruits
	| journal = ]
	| volume = 44
	| issue = 4
	| pages = 1096–1099
	| publisher =
	| location =
	| year = 1996
	| url =
	| issn =
	| doi = 10.1021/jf950577d
	| id =
	| accessdate = 14 July 2009
	| last2 = Mau
	| first2 = Jeng-Leun
	| last3 = Wu
	| first3 = Chung-May}}</ref><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 produced mainly semi-synthetically from ], from which it gets its name. It is a key intermediate in the production of several fragrances. α-Myrcene is the name for the structural isomer 2-methyl-6-methylene-1,7-octadiene, which is not found in nature and is little used.<ref name=Arno>Arno, B. and Leif, J., "Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review", ChemSusChem, 2009, volume 2, pp. 1072-1095. {{DOI|10.1002/cssc.200900186}}</ref>
			==Production==
	==Biosynthesis and production==
			].]]
	Terpenes arises naturally from dehydration of terpenol ]. It could in principle be extract from any number of plants, for example ], the leaves of which contain up to 40% by weight of myrcene. The current route to commercial samples is by the ] (400 °C) of ], which is obtained from ].<ref name=Arno/>
			Myrcene is often produced commercially by the ] (400&nbsp;°C) of β-], which is obtained from ].<ref name=Behr/> It is rarely obtained directly from plants.<ref name=UllmannEgg>{{cite encyclopedia|author=M. Eggersdorfer |title=Terpenes|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a26_205|isbn=3-527-30673-0}}</ref>
			Plants biosynthesize myrcene via ] (GPP), which isomerizes into ] pyrophosphate. An ], releasing the ] (OPP) and a proton, completes the conversion.<ref>{{Cite book|title=Medicinal Natural Products: A Biosynthetic Approach|last=Dewick|first=Paul M.|publisher=John Wiley and Sons, Ltd.|year=2002|isbn=0-471-49641-3|location=New York|page=174|url=https://books.google.com/books?id=A4zptjOJfKQC}}</ref>
	==Use in fragrance industry==
	Myrcene is an important intermediate used in the perfumery industry. It has pleasant odor, but is rarely used directly. It is also unstable in air, tending to ]ize. Samples are stabilized by the addition of alkylphenols or ]. It is thus more highly valued as an intermediate for the preparation of flavor and fragrance chemicals such as ], ], ], ], ], ], and ]. Treatment of myrcene with ] give geranyl chloride, neryl chloride, and linalyl chloride. Treatment of these compounds with ] gives geranyl acetate, neryl acetate, and linalyl acetate, respectively. These esters are then ] to the corresponding alcohols. Myrcene is also converted to ], another fragrance found in ] via uncatalyzed ] of the 1,3-diene followed by hydrolysis and Pd-catalyzed removal of the amine.
			==Occurrence==
	As 1,3-dienes, both myrcene and mycenol undergo ]s with several ]s such as ] to give cyclohexene derivatives that are also useful fragrances.<ref name=Ullmann>Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg “Flavors and Fragrances” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a11_141}}</ref>
			It could in principle be extracted from any number of plants, such as ] or ],<ref name=UllmannEgg/> the leaves of which contain up to 40% by weight of myrcene.{{cn|date=September 2021}} Many other plants contain myrcene, sometimes in substantial amounts.<ref name=Behr/> Some of these include cannabis,<ref name="Booth">{{cite journal | last1=Booth | first1=Judith K. | last2=Page | first2=Jonathan E. | last3=Bohlmann | first3=Jörg | editor-last=Hamberger | editor-first=Björn | title=Terpene synthases from ''Cannabis sativa'' | journal=PLOS ONE| volume=12 | issue=3 | date=29 March 2017 | issn=1932-6203 | doi=10.1371/journal.pone.0173911 | page=e0173911|pmid=28355238|pmc=5371325| bibcode=2017PLoSO..1273911B | doi-access=free }}</ref> hops, '']'', ], ], ''Myrcia'', ], and ].<ref>{{cite journal|pmid=15453700|year=2004|last1=Marongiu|first1=B|title=Comparative analysis of the oil and supercritical CO2 extract of ''Elettaria cardamomum'' (L.) Maton|journal=Journal of Agricultural and Food Chemistry|volume=52|issue=20|pages=6278–82|last2=Piras|first2=A|last3=Porcedda|first3=S|doi=10.1021/jf034819i}}</ref>
			Of the several terpenes extracted from '']'' (hops), the largest monoterpenes fraction is β-myrcene. One study of the chemical composition of the fragrance of '']'' found β-myrcene to compose between 29.4% and 65.8% of the steam-distilled essential oil for the set of fiber and drug strains tested.<ref>{{Cite web|url=http://druglibrary.net/olsen/HEMP/IHA/jiha4208.html|title=Essential oil of ''Cannabis sativa'' L. strains|website=druglibrary.net|access-date=2017-06-08}}</ref> Additionally, myrcene is thought to be the predominant terpene found in modern cannabis cultivars within North America. Interestingly, photo-oxidation of myrcene has been shown to rearrange the molecule into a novel terpene known as "hashishene" which is named for its abundance in hashish.<ref>{{Cite web|title=Myrcene Terpene for Extracts, vape and concentrates|url=https://www.elevationterpenes.com/products/myrcene-terpene-for-extracts-vape-and-concentrates|access-date=2020-12-03|website=ElevationTerpenes}}</ref>
	== Compendial status ==
	* ]<ref name=ib29>{{cite web
	| last = The British Pharmacopoeia Secretariat
	| first =
	| authorlink =
	| coauthors =
	| title = Index, BP 2009
	| work =
	| publisher =
	| year = 2009
	| url = http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
	| format =
	| doi =
	| accessdate = 31 March 2010}}</ref>
			It is found in the South African '']'' (50%).<ref>{{Cite journal|url=https://agris.fao.org/agris-search/search.do?recordID=US201301099695|title = Composition of the essential oils of two Adenandra species from South Africa|journal = Journal of Essential Oil Research |year = 2006|last1 = Baser|first1 = K. H. C.|last2 = Demirci|first2 = B.|last3 = Ozek|first3 = T.|last4 = Viljoen|first4 = A. M.|last5 = Victor|first5 = J. E.}}</ref> & Brazilian '']'' (40%)<ref>{{cite journal |doi=10.1016/j.foodcont.2018.07.034|title=Essential oil from pink pepper (Schinus terebinthifolius Raddi): Chemical composition, antibacterial activity and mechanism of action |year=2019 |last1=Dannenberg |first1=Guilherme da Silva |last2=Funck |first2=Graciele Daiana |last3=Silva |first3=Wladimir Padilha da |last4=Fiorentini |first4=Ângela Maria |journal=Food Control |volume=95 |pages=115–120 |s2cid=92548775 }}</ref> Myrcene is also found in '']'' ] (up to 48%),<ref>{{cite journal|doi=10.1002/ffj.1242|title=Essential oils from three ''Myrcia'' species |year=2003 |last1=Zoghbi |first1=M das Graças B. |last2=Andrade |first2=Eloisa Helena A. |last3=Da Silva |first3=Milton Helio L. |last4=Carreira |first4=L. M. M. |last5=Maia |first5=J. G. S. |journal=Flavour and Fragrance Journal |volume=18 |issue=5 |pages=421–424 }}</ref> ], ], ], and ].<ref name=Behr/><ref name=csoc>{{cite journal | last1 = Chyau | first1 = C.-C. | last2 = Mau | first2 = J.-L. | last3 = Wu | first3 = C.-M. | title = Characteristics of the Steam-Distilled Oil and Carbon Dioxide Extract of ''Zanthoxylum simulans'' Fruits | journal = ] | year = 1996 | volume = 44 | issue = 4 | pages = 1096–1099 | doi = 10.1021/jf950577d}}</ref>
	==Partial list of the plants that contain myrcene==
	As mentioned above, many plants contain myrcene, sometimes in very large amounts.<ref name=Arno/>
	* ]
	* ]
	* ] spp.
	* ]
	* ]
	* ]
	* ]
	* ]
			==Use in fragrance and flavor industries==
	==References==
			Myrcene is an intermediate used in the ] industry. It has a pleasant odor but is rarely used directly.<ref name=Behr/> It is also unstable in air, tending to ]ize. Samples are stabilized by the addition of alkylphenols or ]. It is thus more highly valued as an intermediate for the preparation of flavor and fragrance chemicals, such as ], ], ], ], ], ], and ].<ref name=UllmannEgg/>
	{{reflist}}
			Both myrcene and myrcenol undergo ]s with several ]s, such as ], to give ] derivatives that are also useful fragrances, for instance ].<ref name=Ullmann>{{cite encyclopedia |author1=Fahlbusch, K.-G. |author2=Hammerschmidt, F.-J. |author3=Panten, J. |author4=Pickenhagen, W. |author5=Schatkowski, D. |author6=Bauer, K. |author7=Garbe, D. |author8=Surburg, H. | encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry | year = 2002 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a11_141 |chapter=Flavors and Fragrances |isbn=3-527-30673-0}}</ref>
			Myrcene also contributes a peppery and balsam aroma in beer.<ref>{{cite journal|pmid=23627300|year=2013|last1=Inui|first1=T|title=Different beers with different hops. Relevant compounds for their aroma characteristics|journal=Journal of Agricultural and Food Chemistry|volume=61|issue=20|pages=4758–64|last2=Tsuchiya|first2=F|last3=Ishimaru|first3=M|last4=Oka|first4=K|last5=Komura|first5=H|doi=10.1021/jf3053737}}</ref><ref>{{cite journal|pmid=23483584|year=2013|last1=Vázquez Araújo|first1=L.|title=Use of hydrodistillation and headspace solid-phase microextraction to characterize the volatile composition of different hop cultivars|journal=Journal of the Science of Food and Agriculture|volume=93|issue=10|pages=2568–74|last2=Rodríguez Solana|first2=R|last3=Cortés Diéguez|first3=S. M.|last4=Domínguez|first4=J. M.|doi=10.1002/jsfa.6078|bibcode=2013JSFA...93.2568V }}</ref>
			As of October 2018, the ] withdrew authorization for the use of myrcene as a synthetic flavoring substance for use in food, without regard to its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use.<ref>{{Federal Register|83|50490}}</ref>
			== Health and safety ==
			In 2015, beta-myrcene was added to ] list of chemicals known to the state of California to cause cancer or reproductive harm.<ref>{{cite web |title=Proposition 65 |url=https://oehha.ca.gov/proposition-65/chemicals/beta-myrcene |website=oehha.ca.gov |publisher=OEHHA - California Office of Environmental Health Hazard Assessment}}</ref>
	== See also ==		== See also ==
	* ]		* ]
			== References ==
			{{reflist}}
	]		]
	]		]
	]
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]