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词条 Eugenol
释义

  1. Modern uses

  2. Biosynthesis

  3. Toxicity

  4. Allergy

  5. Natural occurrence

  6. See also

  7. References

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 408562645
| Name = Eugenol
| 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/cm3
| pKa = 10.19 at 25{{nbsp}}°C
| MagSus = {{val|-1.021|e=-4|u=cm3/mol}}
|Section3={{Chembox Hazards
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| FlashPtC = 104
|Section8={{Chembox Related
| OtherCompounds = 2-Phenethyl propionate
}}Eugenol {{IPAc-en|ˈ|j|uː|dʒ|ᵻ|n|ɒ|l}} is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds.[1] It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf.[2][3][4][5] It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil.[6] Eugenol has a pleasant, spicy, clove-like scent.[7] The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The current Linnean nomenclature term for cloves is Syzygium aromaticum.[8]

Modern uses

Eugenol is used in perfumes, flavorings, and essential oils. It is also used as a local antiseptic and anaesthetic.[9][10] Eugenol can be combined with zinc oxide to form zinc oxide eugenol which has restorative and prosthodontic applications in dentistry. For persons with a dry socket as a complication of tooth extraction, packing the dry socket with a eugenol-zinc oxide paste on iodoform gauze is effective for reducing acute pain.[11] Eugenol-Zinc oxide paste is also used for root canal sealing.[12]

It is one of many compounds that is attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.[13] It also attracts female cucumber beetles.[14] It was recently discovered that eugenol and isoeugenol, floral volatile scent compounds, are catalyzed by a single type of enzyme in the genus Gymnadenia and the gene encoding for this enzyme is the first functionally characterized gene in these species so far.[15]

Clove oil is growing in popularity as an anaesthetic for use on aquarium fish as well as on wild fish when sampled for research and management purposes.[16][17] Where readily available, it presents a humane method to euthanise sick and diseased fish either by direct overdose or to induce sleep before an overdose of eugenol.[18]

Biosynthesis

The biosynthesis of eugenol begins with the amino acid tyrosine. L-tyrosine is converted to p-coumaric acid by the enzyme tyrosine ammonia lyase (TAL).[19] From here, p-coumaric acid is converted to caffeic acid by p-coumarate 3-hydroxylase using oxygen and NADPH. S-Adenosyl methionine (SAM) is then used to methylate caffeic acid, forming ferulic acid, which is in turn converted to feruloyl-CoA by the enzyme 4-hydroxycinnamoyl-CoA ligase (4CL).[20] Next, feruloyl-CoA is reduced to coniferaldehyde by cinnamoyl-CoA reductase (CCR). Coniferaldeyhyde is then further reduced to coniferyl alcohol by cinnamyl-alcohol dehydrogenase (CAD) or sinapyl-alcohol dehydrogenase (SAD). Coniferyl alcohol is then converted to an ester in the presence of the substrate CH3COSCoA, forming coniferyl acetate. Finally, coniferyl acetate is converted to eugenol via the enzyme eugenol synthase 1 and the use of NADPH.

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Toxicity

Eugenol is hepatotoxic, meaning it may cause damage to the liver.[21][22] Overdose is possible, causing a wide range of symptoms from blood in the patient's urine, to convulsions, diarrhoea, nausea, unconsciousness, dizziness, or rapid heartbeat.[23] According to a published 1993 report, a 2-year-old boy nearly died after taking between 5 and 10 ml.[24]

Allergy

Eugenol is subject to restrictions on its use in perfumery[25] as some people may become sensitised to it, however, the degree to which eugenol can cause an allergic reaction in humans is disputed.[26]

Eugenol is a component of balsam of Peru, to which some people are allergic.[27][28] When eugenol is used in dental preparations such as surgical pastes, dental packing, and dental cement, it may cause contact stomatitis and allergic cheilitis.[27] The allergy can be discovered via a patch test.[27]

Natural occurrence

Eugenol naturally occurs in several plants, including the following:

{{div col|colwidth=20em}}
  • Cloves (Syzygium aromaticum)[29][30][31]
  • Wormwood{{citation needed|date=August 2017}}
  • Cinnamon[30][32]
  • Cinnamomum tamala[33]
  • Nutmeg (Myristica fragrans)[34]
  • Ocimum basilicum (sweet basil)[35]
  • Ocimum gratissimum (African basil)[15][36]
  • Ocimum tenuiflorum (syn. Ocimum sanctum, tulsi or holy basil)
  • Japanese star anise[37]
  • Lemon balm[38]
  • Dill{{citation needed|date=August 2017}}
  • Pimenta racemosa{{citation needed|date=August 2017}}
  • Vanilla{{citation needed|date=August 2017}}
  • Bay laurel{{citation needed|date=August 2017}}
  • Celery{{citation needed|date=August 2017}}
  • Ginger{{citation needed|date=August 2017}}
{{div col end}}

See also

  • Zinc oxide eugenol
  • Pseudoisoeugenol
  • Isoeugenol
  • Ferulic acid

References

1. ^National Center for Biotechnology Information. PubChem Compound Database; CID=3314, https://pubchem.ncbi.nlm.nih.gov/compound/3314 (accessed Feb. 26, 2019).
2. ^{{cite journal|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/publication/228673419|format=PDF}}
3. ^{{cite journal|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 |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. }}
4. ^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 }}
5. ^{{cite web|url=http://www.thegoodscentscompany.com/gca/gc1101071.html |title=Typical G.C. for bay leaf oil |publisher=Thegoodscentscompany.com |accessdate=2014-04-27}}
6. ^{{cite book | 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 }}
7. ^{{Cite web|url=http://www.hmdb.ca/metabolites/HMDB0005809|title=Human Metabolome Database: Showing metabocard for Eugenol (HMDB0005809)|website=www.hmdb.ca|access-date=2018-07-01}}
8. ^{{cite journal |vauthors=Cortés-Rojas DF, de Souza CR, Oliveira WP |title=Clove (Syzygium aromaticum): a precious spice |journal=Asian Pac J Trop Biomed |volume=4 |issue=2 |pages=90–6 |date=February 2014 |pmid=25182278 |pmc=3819475 |doi=10.1016/S2221-1691(14)60215-X |url=}}
9. ^{{cite journal|journal=Pharmacology|year=1976|volume=14|issue=4|pages=367–77|title=Anesthetic action of methyleugenol and other eugenol derivatives.|last1=Sell|first1= AB|last2=Carlini|first2=EA|doi=10.1159/000136617|pmid=935250}}
10. ^{{cite journal|last1=Jadhav |first1=B. K. |last2=Khandelwal |first2=K. R. |last3=Ketkar |first3=A. R. |last4=Pisal |first4=S. S.|title=Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases|journal=Drug Development and Industrial Pharmacy|date=February 2004|volume=30|issue=2|pages=195–203|pmid=15089054 |doi=10.1081/DDC-120028715}}
11. ^{{cite journal |vauthors=Tarakji B, Saleh LA, Umair A, Azzeghaiby SN, Hanouneh S |title=Systemic review of dry socket: aetiology, treatment, and prevention |journal=J Clin Diagn Res |volume=9 |issue=4 |pages=ZE10–3 |date=April 2015 |pmid=26023661 |pmc=4437177 |doi=10.7860/JCDR/2015/12422.5840 |url=}}
12. ^{{cite book |first= Jack L.|last= Ferracane | title = Materials in Dentistry: Principles and Applications | date = 2001 | edition = 2nd | publisher = Lippincott, Williams & Wilkins | isbn = 978-0-7817-2733-4}}
13. ^{{cite journal |url=http://springerlink.com/content/kv52574k74438848/ |last1=Schiestl |first1=F. P. |last2=Roubik |first2=D. W. |date=January 2003 |title=Odor Compound Detection in Male Euglossine Bees |journal=Journal of Chemical Ecology |volume=29 |issue=1 |pages=253–257 |pmid=12647866 |doi=10.1023/A:1021932131526 |access-date=4 February 2009 |archive-url=https://archive.is/20130203133804/http://springerlink.com/content/kv52574k74438848/ |archive-date=3 February 2013 |dead-url=yes |df=dmy-all }}
14. ^{{cite web|url=http://attra.ncat.org/attra-pub/cucumberbeetle.html|title=Cucumber Beetles: Organic and Biorational Integrated Pest Management (Summary)|publisher=Attra.ncat.org|date=2013-08-05|accessdate=2014-04-27}}
15. ^1 {{cite journal |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 }}
16. ^{{cite conference|title=Anesthesia, Analgesia, and Surgery in Pet Fish|url=http://www.vin.com/VINDBPub/SearchPB/Proceedings/PR05000/PR00342.htm|work=Atlantic Coast Veterinary Conference|date=2001|accessdate=2014-03-17}}
17. ^{{cite journal|last=Grush|first=J.|last2=Noakes|first2=D. L. G. |last3=Moccia|first3=R. D. |title=The Efficacy of Clove Oil As An Anesthetic for the Zebrafish|journal=Zebrafish|date=February 2004|volume=1|issue=1|pages=46–53|doi=10.1089/154585404774101671|pmid=18248205}}
18. ^{{cite web| url = http://www.fishchannel.com/media/fish-health/euthanasia.aspx.pdf| title = Aquarium Fish Euthanasia| author = Monks, Neale| accessdate = 2010-12-07 | date = 2009-04-02| publisher = Fish Channel}}
19. ^{{cite book|last1=Dewick |first1=P. M. |title=Medicinal Natural Products |publisher=John Wiley & Sons |date=2009 |doi=10.1002/9780470742761|isbn=9780470742761 }}
20. ^{{cite journal|last=Harakava |first=R. |title=Genes encoding enzymes of the lignin biosynthesis pathway in Eucalyptus |journal=Genet. Mol. Biol. |volume=28 |pages=601–607 |date=2005}}
21. ^{{cite journal | 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 = Toxicology and Applied Pharmacology}}
22. ^{{cite journal | 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}}
23. ^{{cite news|url=http://health.nytimes.com/health/guides/poison/eugenol-oil-overdose/overview.html |title=Eugenol Oil Overdose |newspaper=The New York Times}}
24. ^{{cite journal | 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}}
25. ^{{cite web|url=http://www.ifraorg.org/en-us/standards_restricted/s3/p4|website=www.ifraorg.org|title=IFRA |deadurl=yes |archiveurl=https://web.archive.org/web/20111230042603/http://www.ifraorg.org/en-us/standards_restricted/s3/p4 |archivedate=2011-12-30 }}
26. ^{{cite web|url=http://www.leffingwell.com/Cropwatch%20Claims%20Victory%20Over%2026%20Allergens.pdf |title=Cropwatch Claims Victory Regarding "26 Allergens" Legislation |publisher=www.leffingwell.com |accessdate=2014-04-27}}
27. ^1 2 {{cite book|url=https://books.google.com/books?id=mrreTHuo54wC&pg=PA352&dq=%22balsam+of+peru%22+%22eugenol%22#v=onepage&q=%22balsam%20of%20peru%22%20%22eugenol%22&f=false |title=Biocompatibility of Dental Materials |first1=Gottfried |last1=Schmalz |first2=Dorthe Arenholt |last2=Bindslev |publisher= |accessdate=2014-04-27|isbn=9783540777823 |date=2008-10-10 }}
28. ^{{cite book|first=Derk P. |last=Bruynzeel |title=Management of Positive Patch Test Reactions |pages=53–55 |publisher=Springer |date=2014 |doi=10.1007/978-3-642-55706-4_11|chapter=Balsam of Peru (Myroxylon pereirae) |isbn=978-3-540-44347-6 }}
29. ^{{cite journal|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.}}
30. ^1 {{cite journal|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}}
31. ^{{cite journal|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}}
32. ^{{cite journal|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+-K+-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}}
33. ^{{cite journal|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}}
34. ^{{cite journal|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}}
35. ^{{cite journal|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.}}
36. ^{{cite journal|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=Memórias 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}}
37. ^{{cite journal|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 = Peña|first6 = B. M.}}
38. ^{{cite web|url = http://www.umm.edu/altmed/articles/lemon-balm-000261.htm|title = Lemon balm|accessdate = 2010-12-07|publisher = University of Maryland Medical Center}}
{{Stomatological preparations}}{{Phenylpropene}}{{Transient receptor potential channel modulators}}{{Use dmy dates|date=January 2011}}

7 : Phenylpropenes|Flavors|Perfume ingredients|Phenols|Allyl compounds|O-Methylated natural phenols|O-Methylated phenylpropanoids
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