loader
Please Wait
Applying Filters...

Technical details about Eugenol, learn more about the structure, uses, toxicity, action, side effects and more

Menu
$ API Ref.Price (USD/KG) : 20Xls
2D Structure
Also known as: 97-53-0, 4-allyl-2-methoxyphenol, 4-allylguaiacol, Eugenic acid, Allylguaiacol, Caryophyllic acid
Molecular Formula
C10H12O2
Molecular Weight
164.20  g/mol
InChI Key
RRAFCDWBNXTKKO-UHFFFAOYSA-N
FDA UNII
3T8H1794QW

A cinnamate derivative of the shikimate pathway found in CLOVE OIL and other PLANTS.
Eugenol is a Standardized Chemical Allergen. The physiologic effect of eugenol is by means of Increased Histamine Release, and Cell-mediated Immunity.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methoxy-4-prop-2-enylphenol
2.1.2 InChI
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
2.1.3 InChI Key
RRAFCDWBNXTKKO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=C(C=CC(=C1)CC=C)O
2.2 Other Identifiers
2.2.1 UNII
3T8H1794QW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Phenol, 2-methoxy-4-(2-propenyl)-

2.3.2 Depositor-Supplied Synonyms

1. 97-53-0

2. 4-allyl-2-methoxyphenol

3. 4-allylguaiacol

4. Eugenic Acid

5. Allylguaiacol

6. Caryophyllic Acid

7. P-allylguaiacol

8. 2-methoxy-4-prop-2-enylphenol

9. P-eugenol

10. Engenol

11. 2-methoxy-4-allylphenol

12. Phenol, 2-methoxy-4-(2-propenyl)-

13. 2-methoxy-4-(2-propenyl)phenol

14. 1,3,4-eugenol

15. 4-allylcatechol-2-methyl Ether

16. 1-hydroxy-2-methoxy-4-allylbenzene

17. 5-allylguaiacol

18. Synthetic Eugenol

19. 2-methoxy-1-hydroxy-4-allylbenzene

20. 4-allyl-1-hydroxy-2-methoxybenzene

21. 1-hydroxy-2-methoxy-4-prop-2-enylbenzene

22. 2-methoxy-4-(prop-2-en-1-yl)phenol

23. Eugenol (natural)

24. Fema No. 2467

25. 4-hydroxy-3-methoxy-1-allylbenzene

26. 2-hydroxy-5-allylanisole

27. Bioxeda

28. Dentogum

29. 4-allylcatechol 2-methyl Ether

30. 4-hydroxy-3-methoxyallylbenzene

31. 2-methoxy-4-(2-propen-1-yl)phenol

32. Phenol, 4-allyl-2-methoxy-

33. Nci-c50453

34. 1-allyl-4-hydroxy-3-methoxybenzene

35. 1-allyl-3-methoxy-4-hydroxybenzene

36. 2-metoksy-4-allilofenol

37. Caryophillic Acid

38. Fa 100

39. Eugenol [usp]

40. Nsc 209525

41. Chebi:4917

42. Phenol, 2-methoxy-4-(2-propen-1-yl)-

43. Nsc-8895

44. Nsc-209525

45. Chembl42710

46. 2-methoxy-4-(3-propenyl)phenol

47. 3t8h1794qw

48. Eugenol (usp)

49. Ncgc00091449-05

50. Dsstox_cid_617

51. Dsstox_rid_75693

52. Dsstox_gsid_20617

53. Eugenol [usan]

54. Wln: 1u2r Dq Co1

55. Phenol, 2-methoxy-4-(2-propen-1-yl)-, Homopolymer

56. Caswell No. 456bc

57. Fema Number 2467

58. Cas-97-53-0

59. 38219-15-7

60. Ccris 306

61. Hsdb 210

62. 2-metoksy-4-allilofenol [polish]

63. Sr-05000002043

64. Einecs 202-589-1

65. Mfcd00008654

66. Epa Pesticide Chemical Code 102701

67. Brn 1366759

68. Unii-3t8h1794qw

69. Ai3-00086

70. Eugenol,(s)

71. 4-allyl-2methoxyphenol

72. 3s0e

73. Eugenol [vandf]

74. Eugenol [fhfi]

75. Eugenol [hsdb]

76. Eugenol [iarc]

77. Eugenol [inci]

78. Eugenol [fcc]

79. Eugenol [ii]

80. Eugenol [mi]

81. Eugenol [mart.]

82. Spectrum2_001264

83. Spectrum3_000646

84. Spectrum4_001783

85. Spectrum5_000425

86. Eugenol [usp-rs]

87. Eugenol [who-dd]

88. 4-allyl-2-methoxy-phenol

89. Bmse010053

90. Epitope Id:114091

91. Eugenol, Puriss., 98%

92. Ec 202-589-1

93. Schembl20361

94. Bspbio_002251

95. Kbiogr_002327

96. Mls000028901

97. Bidd:er0696

98. Divk1c_000692

99. Spectrum1500296

100. Spbio_001228

101. Eugenol [ep Monograph]

102. Gtpl2425

103. Zinc1411

104. Eugenol [usp Monograph]

105. Dtxsid9020617

106. Hms502c14

107. Kbio1_000692

108. Kbio3_001471

109. Eugenol, Reagentplus(r), 99%

110. Nsc8895

111. 4-(2-propenyl)-2-methoxyphenol

112. Eugenol, Natural, >=98%, Fg

113. Ninds_000692

114. Eugenol, >=98%, Fcc, Fg

115. Hms1920o08

116. Hms2091f09

117. Pharmakon1600-01500296

118. Hy-n0337

119. Tox21_111134

120. Tox21_202040

121. Tox21_300105

122. Bbl027721

123. Bdbm50164168

124. Ccg-38827

125. Nsc209525

126. Nsc757030

127. S4706

128. Stl371304

129. Eugenol, Tested According To Ph.eur.

130. 3-(3-methoxy-4-hydroxyphenyl)propene

131. Akos000121354

132. Tox21_111134_1

133. Cs-7807

134. Db09086

135. Fs-2702

136. Nsc-757030

137. Sdccgmls-0066578.p001

138. Idi1_000692

139. Eugenol 1000 Microg/ml In Acetonitrile

140. Ncgc00091449-01

141. Ncgc00091449-02

142. Ncgc00091449-03

143. Ncgc00091449-04

144. Ncgc00091449-06

145. Ncgc00091449-07

146. Ncgc00091449-08

147. Ncgc00091449-10

148. Ncgc00253915-01

149. Ncgc00259589-01

150. Ac-34149

151. Eugenol, Vetec(tm) Reagent Grade, 98%

152. Smr000059114

153. Sbi-0051381.p003

154. Eugenol, Pestanal(r), Analytical Standard

155. A0232

156. Ft-0615974

157. N1805

158. D04117

159. Ab00051992_02

160. A845719

161. Eugenol, Primary Pharmaceutical Reference Standard

162. Q423357

163. Eugenol, Certified Reference Material, Tracecert(r)

164. Q-201105

165. Sr-05000002043-1

166. Sr-05000002043-2

167. Brd-k32977963-001-01-9

168. Brd-k32977963-001-03-5

169. Eugenol (constituent Of Holy Basil Leaf) [dsc]

170. Eugenol, European Pharmacopoeia (ep) Reference Standard

171. F0001-2306

172. 2-methoxy-4-(prop-2-en-1-yl)phenol4-allyl-2-methoxyphenol

173. Eugenol (constituent Of Cinnamomum Cassia Bark) [dsc]

174. Eugenol (constituent Of Cinnamomum Verum Bark) [dsc]

175. Eugenol, United States Pharmacopeia (usp) Reference Standard

176. Eugenol, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 164.20 g/mol
Molecular Formula C10H12O2
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass164.083729621 g/mol
Monoisotopic Mass164.083729621 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count12
Formal Charge0
Complexity145
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

... Has been used as an antipyretic but it is relatively ineffective. /Eugenol/ has... been used in medicine for the study of mucous secretion /and/ gastric cytology, without gastric resection or gastroenterostomy. It has been shown to have anthelmintic properties. /SRP: Former use/

Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1691


Nonprescription medicines for toothache commonly contain eugenol, and some products for canker-sore may do so also.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 78 (1985)


Eugenol is used as a component of several dental materials (e.g., dental cements, impression pastes and surgical pastes). Such products are principally combinations of zinc oxide and eugenol in varying ratios. They are reported to be widely used in dentistry as temporary filing materials, cavity liners for pulp protection, capping materials, temporary cementation of fixed protheses, impression materials and major ingredients of endodontic sealers. In addition, eugenol has been used in dentistry for disinfecting root canals.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 77 (1985)


Analgesic (dental)

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 690


4.2 Drug Indication

Eugenol is not currently available in any FDA-approved drug products. There are a number of unapproved OTC products that advertise it for the use of toothache. Eugenol is is also commonly used in combination with zinc oxide in dental procedures for the cementation of temporary prostheses and the temporary restoration of teeth and cavities.


FDA Label


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)


Solvents

Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant and Hackh's Chemical Dictionary, 5th ed) (See all compounds classified as Solvents.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
EUGENOL
5.2.2 FDA UNII
3T8H1794QW
5.2.3 Pharmacological Classes
Cell-mediated Immunity [PE]; Increased Histamine Release [PE]; Standardized Chemical Allergen [EPC]; Allergens [CS]
5.3 Absorption, Distribution and Excretion

Intraperitoneal injection of a single 450 mg/kg dose of (14)C methoxy labelled eugenol resulted in rapid distribution to all organs. Both ether- and water soluble materials were recovered from most tissues and excretions. Only 0.2-1.0% of the dose was eliminated as expired (14)CO2. Over 70% of a lethal dose of eugenol was recovered on death, from the urine of rabbits.

WHO; Food Additive Series 17: Eugenol (1980). Available from, as of April 21, 2005: https://www.inchem.org/documents/jecfa/jecmono/v17je10.htm


No penetration of mouse skin was demonstrated after dermal application of eugenol.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 86 (1985)


5.4 Metabolism/Metabolites

Following ip injection of (14)C eugenol into rats, ... the presence of (14)CO2 in expired air indicated the demethylation of eugenol.

Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon Press, 1979., p. 376


The metabolism and toxic effects of eugenol were studied in isolated rat hepatocytes. Incubation of hepatocytes with eugenol resulted in the formation of conjugates with sulfate, glucuronic acid and glutathione. The major metabolite formed was the glucuronic acid conjugate. Covalent binding to cellular protein was observed using (3)H eugenol. Loss of intracellular glutathione and cell death were also observed in these incubations. Concentrations of 1 mM eugenol caused a loss of over 90% of intracellular glutathione and resulted in approximately 85% cell death over a 5 hr incubation period. The loss of the majority of glutathione occurred prior to the onset of cell death (2 hr). The effects of eugenol were concentration dependent. The addition of 1 mM N-acetylcysteine to incubations containing 1 mM eugenol was able to completely prevent glutathione loss and cell death as well as inhibit the covalent binding of eugenol metabolites to protein. Conversely, pretreatment of hepatocytes with diethylmaleate to deplete intracellular glutathione increased the cytotoxic effects of eugenol. These results demonstrate that eugenol is actively metabolized in hepatocytes and suggest that the cytotoxic effects of eugenol are due to the formation of a reactive intermediate, possibly a quinone methide.

PMID:1991333 Thompson DC et al; Chem Biol Interact 77 (2): 137-47 (1991)


Two metabolites of eugenol, 3-piperidyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone and 3-pyrrolidinyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone, have been isolated from rat urine.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 86 (1985)


Epoxidation of eugenol by rat liver cell cultures has been reported. The dihydrodiol metabolite of eugenol has been isolated from liver homogenates and urine of rats pretreated with eugenol.

WHO; Food Additive Series 17: Eugenol (1980). Available from, as of April 21, 2005: https://www.inchem.org/documents/jecfa/jecmono/v17je10.htm


For more Metabolism/Metabolites (Complete) data for EUGENOL (9 total), please visit the HSDB record page.


Eugenol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-(2-methoxy-4-prop-2-enylphenoxy)oxane-2-carboxylic acid and Hydroxychavicol.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.5 Mechanism of Action

The exact mechanism of action of eugenol is unknown. However, eugenol has been shown to interrupt action potentials, which may be involved in its anti-pain activity. Research has also shown eugenol to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties.


... Thymocyte suspension was irradiated by gamma-rays, and the malondialdehyde (MDA) formation was measured with the thiobarbituric acid reactive species (TBARS) method. The results showed an increase in MDA in irradiated (2 Gy) thymocytes, which was inhibited in samples treated with increasing concentrations of eugenol (10-200 uM) prior to irradiation. The concentration of eugenol required to inhibit half of the MDA formation (IC(50)) in irradiated thymocytes was 100 uM. A dose-dependent increase in the generation of ROS was observed in irradiated thymocytes (0.5-200 cGy) as measured by 2,7-dichlorodihydro fluorescein diacetate (DCH-FDA), which was inhibited by eugenol administered before irradiation.

PMID:15163290 Pandy BN, Mishra KP; J Environ Pathol Toxicol Oncol 23 (2): 117-22 (2004)


Respiratory inhibition of isolated rat liver mitochondria by eugenol was dose related and uncoupled oxidative phosphorylation from electron transfer.

PMID:295190 Cotmore JM et al; Arch Oral Biol 24 (8): 565 (1979)


Polymorphonuclear leukocytes (PMNL) play an important role in the modulation of inflammatory conditions in humans. PMNL cells recruited at the site of inflammation, release inflammatory mediators such as leukotrienes, proteolytic enzymes and reactive oxygen species. Among these, leukotrienes are implicated in pathophysiology of allergic and inflammatory disorders like asthma, allergic rhinitis, arthritis, inflammatory bowel disease and psoriasis. 5-lipoxygenase (5-LO) is the key enzyme in biosynthetic pathway of leukotrienes. Our earlier studies showed that spice phenolic active principles significantly inhibit 5-LO enzyme in human PMNLs. In this study we have further characterized the inhibitory mechanism of eugenol, the active principle of spice-clove on 5-LO enzyme and also its effect on leukotriene C((4)) (LTC(4)). Substrate dependent enzyme kinetics showed that the inhibitory effect of eugenol on 5-LO was of a non-competitive nature. Further, eugenol was found to significantly inhibit the formation of LTC(4) in calcium ionophore A23187 and arachidonic acid (AA) stimulated PMNL cells. These data clearly suggest that eugenol inhibits 5-LO by non-competitive mechanism and also inhibits formation of LTC(4) in human PMNL cells and thus may have beneficial role in modulating 5-LO pathway in human PMNL cells.

PMID:16216483 Raghavenra H et al; Prostaglandins Leukot Essent Fatty Acids 74 (1): 23-7 (2006)


The Ca(2+)-activated Cl(-) channel TMEM16A is involved in epithelial fluid secretion, smooth muscle contraction and neurosensory signaling. We identified a Thai herbal antidiarrheal formulation that inhibited TMEM16A Cl(-) conductance. C18-reversed-phase HPLC fractionation of the herbal formulation revealed >98% of TMEM16A inhibition activity in one out of approximately 20 distinct peaks. The purified, active compound was identified as eugenol (4-allyl-2-methoxyphenol), the major component of clove oil. Eugenol fully inhibited TMEM16A Cl(-) conductance with single-site IC(50)~150 uM. Eugenol inhibition of TMEM16A in interstitial cells of Cajal produced strong inhibition of intestinal contraction in mouse ileal segments. TMEM16A Cl(-) channel inhibition adds to the list of eugenol molecular targets and may account for some of its biological activities.

PMID:22666439 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3364195 Yao Z et al; PLoS One. 2012;7(5):e38030. doi: 10.1371/journal.pone.0038030. Epub 2012 May 30.


For more Mechanism of Action (Complete) data for EUGENOL (21 total), please visit the HSDB record page.