{{위키데이터 속성 추적}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 408562645
| Name = 유제놀
| ImageFile = Eugenol2DCSD.svg
| ImageSize = 240
| ImageAlt = Skeletal formula of eugenol
| ImageFile1 = Eugenol-3D-balls.png
| ImageAlt1 = Ball-and-stick model of the eugenol molecule
| PIN = 2-Methoxy-4-(prop-2-en-1-yl)phenol
| OtherNames = {{ubl|4-Allyl-2-methoxyphenol|2-Methoxy-4-(2-propenyl)phenol|Eugenic acid|Caryophyllic acid|1-Allyl-3-methoxy-4-hydroxybenzene|Allylguaiacol|2-Methoxy-4-allylphenol|4-Allylcatechol-2-methyl ether}}
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 2425
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13876103
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3T8H1794QW
| InChI = 1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
| InChIKey = RRAFCDWBNXTKKO-UHFFFAOYAJ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 42710
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RRAFCDWBNXTKKO-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 97-53-0
| PubChem = 3314
| SMILES = Oc1ccc(cc1OC)CC=C
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4917
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04117
 }}
|Section2={{Chembox Properties
| C=10
| H=12
| O=2
| MeltingPtC = −7.5
| BoilingPtC = 254
| Density = 1.06 g/cm<sup>3</sup>
| pKa = 10.19 at 25{{nbsp}}°C
| MagSus = {{val|-1.021|e=-4|u=cm<sup>3</sup>/mol}}
| Viscosity = {{plainlist|
* 9.12 mPa·s at 20&nbsp;°C
* 5.99 mPa·s at 30&nbsp;°C<ref name="BinghamSpooner1932">{{저널 인용|last1=Bingham|first1=Eugene C.|last2=Spooner|first2=Laurence W. | name-list-style = vanc |title=The Fluidity Method for the Determination of Association. I|journal=Journal of Rheology|volume=3|issue=2|year=1932|pages=221–244|issn=0097-0360|doi=10.1122/1.2116455|bibcode=1932JRheo...3..221B}}</ref>}}
 }}
|Section3={{Chembox Hazards
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| FlashPtC = 104
 }}
|Section8={{Chembox Related
| OtherCompounds = [[2-Phenethyl propionate]]
 }}
}}
'''유제놀'''({{lang|en|eugenol}}, {{IPAc-en|ˈ|juː|dʒ|ᵻ|n|ɒ|l}}), '''유게놀''', '''오이게놀'''은 [[페닐프로펜]]의 액체이다. 유제놀은 [[페닐프로파노이드]]계 화합물에 속한다. 무색에서 엷은 노란색에 이르는 아로마 유액이며 특정한 [[방향유]]로부터, 특히 [[클로브 오일]], [[육두구]], [[계피]], [[바질]], [[월계수 잎]]으로부터 추출한다.<ref>{{저널 인용|title=Constituents of the essential oil from leaves and buds of clove (''Syzigium caryophyllatum'' L.) Alston|journal=Bangladesh Council of Scientific and Industrial Research BCSIR Laboratories|volume=4|pages=451–454|url=https://www.researchgate.net/profile/Mohammad_Bhuiyan9/publication/228673419_Constituents_of_the_essential_oil_from_leaves_and_buds_of_clove_%28Syzigium_caryophyllatum_%28L.%29_Alston%29/file/72e7e51d2a7894d1f0.pdf?ev=pub_int_doc_dl&origin=publication_detail&inViewer=true|format=PDF}}</ref><ref>{{저널 인용 |url=http://onlinelibrary.wiley.com/doi/10.1002/ffj.2730100403/abstract |title=Investigation of the essential oil of cinnamon leaf grown at Bangalore and Hyderabad |journal=Flavour and Fragrance Journal |volume=10 |issue=4 |pages=239–242 |publisher=wiley.com |accessdate=2014-04-27 |doi=10.1002/ffj.2730100403 |year=1995 |last1=Mallavarapu |first1=Gopal R. |last2=Ramesh |first2=S. |last3=Chandrasekhara |first3=R. S. |last4=Rajeswara Rao |first4=B. R. |last5=Kaul |first5=P. N. |last6=Bhattacharya |first6=A. K. |보존url=https://web.archive.org/web/20140524112054/http://onlinelibrary.wiley.com/doi/10.1002/ffj.2730100403/abstract |보존날짜=2014-05-24 |url-status=dead }}</ref><ref>[http://ddr.nal.usda.gov/bitstream/10113/10927/1/IND44023435.pdf Yield and Oil Composition of 38 Basil (''Ocimum basilicum'' L.) Accessions Grown in Mississippi] {{webarchive |url=https://web.archive.org/web/20101015103319/http://ddr.nal.usda.gov/bitstream/10113/10927/1/IND44023435.pdf |date=15 October 2010 }}</ref><ref>{{웹 인용 |url=http://www.thegoodscentscompany.com/gca/gc1101071.html |title=Typical G.C. for bay leaf oil |publisher=Thegoodscentscompany.com |accessdate=2014-04-27 |보존url=https://web.archive.org/web/20140317050150/http://www.thegoodscentscompany.com/gca/gc1101071.html |보존날짜=2014-03-17 |url-status=dead }}</ref> 클로드 버드 오일의 80~90% 농축물, 클로브 잎 오일의 82~88%의 농축물에 존재한다.<ref name="herbmed">{{서적 인용 | isbn = 978-0-85369-623-0 | title = Herbal Medicines | last1 = Barnes | first1 = J. | last2 = Anderson | first2 = L. A. | last3 = Phillipson | first3 = J. D. | year = 2007 | origyear = 1996 | publisher = Pharmaceutical Press | location = London | edition = 3rd | url = http://file.zums.ac.ir/ebook/366-Herbal%20Medicines,%20Third%20edition-Joanne%20Barnes%20J.%20David%20Phillipson%20Linda%20A.%20Anderson-085369623.pdf | format = PDF | 확인날짜 = 2018-03-25 | 보존url = https://web.archive.org/web/20180701140306/http://file.zums.ac.ir/ebook/366-Herbal%20Medicines,%20Third%20edition-Joanne%20Barnes%20J.%20David%20Phillipson%20Linda%20A.%20Anderson-085369623.pdf | 보존날짜 = 2018-07-01 | url-status = dead }}</ref>

== 생합성 ==
[[파일:Eugenol biosynthesis .tif|500px|섬네일|왼쪽|유제놀의 생합성]]
{{-}}

== 독성 ==
유제놀은 [[간독성]]이 있으며 이는 [[간]]에 위해를 줄 수 있음을 의미한다.<ref>{{저널 인용| pmid = 9512727 | year = 1998 | last1 = Thompson | first1 = D. C. | last2 = Barhoumi | first2 = R. | last3 = Burghardt | first3 = R. C. | title = Comparative toxicity of eugenol and its quinone methide metabolite in cultured liver cells using kinetic fluorescence bioassays | volume = 149 | issue = 1 | pages = 55-63 | doi = 10.1006/taap.1997.8348 | journal = [[:en:Toxicology and Applied Pharmacology]]}}</ref><ref>{{저널 인용| pmid = 12126794 | year = 2002 | last1 = Fujisawa | first1 = S. | last2 = Atsumi | first2 = T. | last3 = Kadoma | first3 = Y. | last4 = Sakagami | first4 = H. | title = Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity | volume = 177 | issue = 1 | pages = 39-54 | journal = Toxicology | doi = 10.1016/S0300-483X(02)00194-4}}</ref> 과다 복용은 가능하지만 혈변에서부터 [[경련]], [[설사]], [[구역질]], [[무의식]], [[어지럼증]], 급속한 [[심박수|심박]]에 이르기까지 다양한 증상을 일으킬 수 있다.<ref>{{웹 인용|url=http://health.nytimes.com/health/guides/poison/eugenol-oil-overdose/overview.html |title=Eugenol Oil Overdose |website=New York Times Health Guide}}</ref> 1993년 출판된 보고서에 따르면 2세 소년은 5~10 밀리리터를 복용한 후 거의 사망에 이를 정도였다.<ref>{{저널 인용| pmid = 8215554 | year = 1993 | last1 = Hartnoll | first1 = G. | last2 = Moore | first2 = D. | last3 = Douek | first3 = D. | title = Near fatal ingestion of oil of cloves | volume = 69 | issue = 3 | pages = 392-393 | pmc = 1029532 | journal = Archives of Disease in Childhood | doi = 10.1136/adc.69.3.392}}</ref>

== 알레르기 ==
유제놀은 [[향수]]에 사용하는 것이 제한되는데<ref>{{웹 인용|url=http://www.ifraorg.org/en-us/standards_restricted/s3/p4|website=www.ifraorg.org|url-status=dead |archiveurl=https://web.archive.org/web/20111230042603/http://www.ifraorg.org/en-us/standards_restricted/s3/p4 |archivedate=2011-12-30 }}</ref> 일부 사람들이 그에 민감해질 수 있기 때문이지만 유제놀이 인간에 미치는 알레르기 반응을 일으키는 정도에 대해서는 논란의 여지가 있다.<ref>{{웹 인용 |url=http://www.leffingwell.com/Cropwatch%20Claims%20Victory%20Over%2026%20Allergens.pdf |publisher=www.leffingwell.com |accessdate=2014-04-27 |제목=보관된 사본 |보존url=https://web.archive.org/web/20140210163144/http://www.leffingwell.com/Cropwatch%20Claims%20Victory%20Over%2026%20Allergens.pdf |보존날짜=2014-02-10 |url-status=dead }}</ref>

== 자연 발생 ==
유제놀은 여러 식물에서 자연적으로 발생하며 다음을 포함한다:
{{colbegin||20em}}
* [[정향나무]] (Syzygium aromaticum)<ref name=tdmq>{{저널 인용|last = Pathak|first = S. B.|title = TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove|journal = Chromatographia|volume = 60|issue = 3-4|pages = 241-244|year = 2004|doi = 10.1365/s10337-004-0373-y|last2 = Niranjan|first2 = K.|last3 = Padh|first3 = H.|last4 = Rajani|first4 = M.}}</ref><ref name = igap>{{저널 인용|last=Bullerman|first=L. B.|last2=Lieu|first2=F. Y.|last3=Seier|first3=S. A.|title=Inhibition of growth and aflatoxin production by cinnamon and clove oils. Cinnamic aldehyde and eugenol|journal=Journal of Food Science|date=July 1977|volume=42|issue=4|pages=1107-1109|doi=10.1111/j.1365-2621.1977.tb12677.x}}</ref><ref name=apae>{{저널 인용|last = Lee|first = Kwang-Geun|first2=Takayuki|last2=Shibamoto| title = Antioxidant property of aroma extract isolated from clove buds [Syzygium aromaticum (L.) Merr. et Perry]|journal = Food Chemistry|volume = 74|issue = 4|pages = 443-448|year = 2001|doi = 10.1016/S0308-8146(01)00161-3}}</ref>
* [[쑥속]]
* [[계피]]<ref name=igap /><ref name=eccs>{{저널 인용|last = Kreydiyyeh|first = S. I.|last2 = Usta|first2 = J.|last3 = Copti| first3 = R.|title = Effect of cinnamon, clove and some of their constituents on the Na<sup>+</sup>-K<sup>+</sup>-ATPase activity and alanine absorption in the rat jejunum|journal = [[Food and Chemical Toxicology]]|volume = 38|issue = 9|pages = 755-762|year = 2000|doi = 10.1016/S0278-6915(00)00073-9|pmid = 10930696}}</ref>
* [[Cinnamomum tamala]]<ref name=qdec>{{저널 인용|last = Dighe|first = V. V.|last2 = Gursale| first2 = A. A.|last3 = Sane|first3 = R. T.|last4 = Menon|first4 = S.|last5 = Patel|first5 = P. H.|title = Quantitative Determination of Eugenol from Cinnamomum tamala Nees and Eberm. Leaf Powder and Polyherbal Formulation Using Reverse Phase Liquid Chromatography|journal = Chromatographia|volume = 61|issue = 9-10|pages = 443-446|year = 2005|doi = 10.1365/s10337-005-0527-6}}</ref>
* [[육두구]] (Myristica fragrans)<ref name=baem>{{저널 인용|last = Bennett|first = A.|last2 = Stamford|first2 = I. F.| last3 = Tavares|first3 = I. A.|last4 = Jacobs|first4 = S.|last5 = Capasso|first5 = F.|last6 = Mascolo|first6 = N.|last7 = Autore|first7 = G.|last8 = Romano|first8 = V.|last9 = Di Carlo|first9 = G.|title = The biological activity of eugenol, a major constituent of nutmeg (..Myristica fragrans..): Studies on prostaglandins, the intestine and other tissues|journal = Phytotherapy Research|volume = 2|issue = 3|pages = 124-130|year = 1988|doi = 10.1002/ptr.2650020305}}</ref>
* [[바질]] (sweet basil)<ref name=osc>{{저널 인용|last = Johnson|first = C. B.|title = Substantial UV-B-mediated induction of essential oils in sweet basil (Ocimum basilicum L.)|journal = Phytochemistry|volume = 51|issue = 4|pages = 507-510|year = 1999|doi = 10.1016/S0031-9422(98)00767-5|last2 = Kirby|first2 = J.|last3 = Naxakis|first3 = G.|last4 = Pearson|first4 = S.}}
</ref>
* [[Ocimum gratissimum]] (African basil)<ref name="Gupta">{{저널 인용|last1=Gupta |first1=A. K. |last2=Schauvinhold |first2=I. |last3=Pichersky |first3=E. |last4=Schiestl |first4=F. P. | date = 2014 | title = Eugenol synthase genes in floral scent variation in ''Gymnadenia'' species | journal = Functional & Integrative Genomics | volume = 14 | issue = 4 | pages = 779–788 | pmid= 25239559| doi = 10.1007/s10142-014-0397-9 }}</ref><ref>{{저널 인용|last=Nakamura|first=C. V.|last2=Ueda-Nakamura|first2=T.|last3=Bando|first3=E.|last4=Melo|first4=A. F. N.|last5=Cortez|first5=D. A. G.|last6=Dias Filho|first6=B. P.|title=Antibacterial activity of Ocimum gratissimum L. essential oil|journal=Memorias do Instituto Oswaldo Cruz|date=September 1999|volume=94|issue=5|pages=675-678|doi=10.1590/S0074-02761999000500022|pmid=10464416|url=http://www.scielo.br/pdf/mioc/v94n5/3781.pdf|format=PDF|확인날짜=2018-03-25|보존url=https://web.archive.org/web/20170823053912/http://www.scielo.br/pdf/mioc/v94n5/3781.pdf|보존날짜=2017-08-23|url-status=dead}}</ref>
* [[Ocimum tenuiflorum]] (syn. Ocimum sanctum, tulsi or holy basil)
* [[붓순나무]]<ref name=jsa>{{저널 인용|title = Neurotoxicities in Infants Seen With the Consumption of Star Anise Tea|journal = Pediatrics|volume = 114|issue = 5|pages = e653-e656|year = 2004|doi = 10.1542/peds.2004-0058|pmid = 15492355|last1 = Ize-Ludlow|first1 = D.|last2 = Ragone|first2 = S.|last3 = Bruck|first3 = I. S.|last4 = Bernstein|first4 = J. N.|last5 = Duchowny|first5 = M.|last6 = Pena|first6 = B. M.}}</ref>
* [[레몬밤]]<ref>{{웹 인용|url = http://www.umm.edu/altmed/articles/lemon-balm-000261.htm|title = Lemon balm|accessdate = 2010-12-07|publisher = [[University of Maryland Medical Center]]}}</ref>
* [[딜]]
* [[Pimenta racemosa]]
* [[바닐라]]
* [[월계수]]
* [[셀러리]]
* [[생강]]
{{colend}}

== 각주 ==
{{각주}}

== 외부 링크 ==
{{위키공용분류}}
* {{웹 인용|last1=Kegley |first1=S. E. |last2=Hill |first2=B. R. |last3=Orme |first3=S. |last4=Choi |first4=A. H. |url=http://www.pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33197#Toxicity |title=Toxicity Information for Eugenol |work=PAN Pesticide Database, |publisher=Pesticide Action Network, North America |location=San Francisco, CA |date=2010}}
* {{웹 인용|url = http://scienceblogs.com/moleculeoftheday/2006/10/eugenol_mmm_dentist.php#commentsArea|title = Eugenol (Mmm, dentist)|accessdate = 7 December 2010|date = 4 October 2006|publisher = [[ScienceBlogs]]|work = Molecule of the Day|url-status = dead|archiveurl = https://web.archive.org/web/20091230101057/http://scienceblogs.com/moleculeoftheday/2006/10/eugenol_mmm_dentist.php#commentsArea|archivedate = 30 December 2009|df = dmy-all}}

[[분류:향료]]
[[분류:페놀류]]
[[분류:O-메틸화 페닐프로파노이드]]