Methyleugenol (BioCAD00000014045)

plant natural products microbial natural products

Metabolite Card

Formula: C11H14O2 (178.0994)
SMILES: COC1=C(OC)C=C(CC=C)C=C1

Synonyms [en]

methyleugenol; O-Methyleugenol; methyl eugenol; eugenol methyl ether; 1,2-Dimethoxy-4-(2-propenyl)benzene; Methyl eugenol ether

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Methyleugenol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000014045). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Methyleugenol, also known as 4-allylveratrole or eugenol methyl, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. FDA noted the action was despite its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use. Methyleugenol is a sweet, anise, and apricot tasting compound. Methyleugenol is found, on average, in the highest concentration within a few different foods, such as allspices, tarragons, and sweet bay and in a lower concentration in sweet basils, rosemaries, and hyssops. Methyleugenol has also been detected, but not quantified, in several different foods, such as soy beans, evergreen blackberries, muskmelons, citrus, and pomes. This could make methyleugenol a potential biomarker for the consumption of these foods. As of October 2018, the US FDA withdrew authorization for the use of methyl eugenol as a synthetic flavoring substance for use in food because petitioners provided data demonstrating that these additives induce cancer in laboratory animals. Methyleugenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Methyl eugenol (allylveratrol) is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and is important to insect behavior and pollination. Their ability to attract insects, particularly Bactrocera fruit flies was first noticed in 1915 by F. M. Howlett. The compound may have evolved in response to pathogens, as methyl eugenol has some antifungal activity. Methyl eugenol is found in a number of plants (over 450 species from 80 families including both angiosperm and gymnosperm families) and has a role in attracting pollinators. About 350 plant species have them as a component of floral fragrance.

Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 20056-58-0
  • CAS Registry Number: 30405-75-5
  • CAS Registry Number: 64118-89-4
  • CAS Registry Number: 93-15-2
  • PubChem: 7127
  • ChEBI: ChEBI:4918
  • HMDB: HMDB0031864
  • KEGG: C10454
  • BioCyc: CPD-6482
  • NCBI MeSH: methyleugenol
  • Wikipedia: Methyl eugenol
  • RefMet: RM0036033
  • MoNA: HMDB0031864_c_ms_100975
  • MoNA: HMDB0031864_c_ms_100976
  • MoNA: HMDB0031864_c_ms_100977
  • MoNA: HMDB0031864_c_ms_100978
  • MoNA: HMDB0031864_c_ms_100979
  • MoNA: JP000747
  • MoNA: JP000748
  • MoNA: JP008424
  • MoNA: JP009443
  • Metlin: METLIN_68336
  • Coconut NaturalProduct: CNP0132145.0
  • Coconut NaturalProduct: CNP0137352.0
  • Coconut NaturalProduct: CNP0310060.0
  • Coconut NaturalProduct: CNP0505524.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R10250 2.1.1.146 S-adenosyl-L-methionine:eugenol O-methyltransferase
Rhea:RHEA:80552 2.1.1.146 eugenol + S-adenosyl-L-methionine => O-methyleugenol + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:80553 2.1.1.146 O-methyleugenol + S-adenosyl-L-homocysteine + H+ => eugenol + S-adenosyl-L-methionine
Rhea:RHEA:80554 2.1.1.146 eugenol + S-adenosyl-L-methionine <=> O-methyleugenol + S-adenosyl-L-homocysteine + H+
BioCyc:RXN-6741 2.1.1.146 S-ADENOSYLMETHIONINE + CPD-6481 --> PROTON + CPD-6482 + ADENOSYL-HOMO-CYS
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Organism Source

Taxonomy Source

  1. Aconitum episcopale [ncbi taxid: 226106]
  2. Aconitum fischeri [ncbi taxid: 1111064]
  3. Aconitum macrorhynchum [ncbi taxid: 3038291]
  4. Acorus calamus [ncbi taxid: 4465]
  5. Acorus gramineus [ncbi taxid: 55184]
  6. Acorus tatarinowii [ncbi taxid: 123564]
  7. Actaea dahurica [ncbi taxid: 64029]
  8. Actaea heracleifolia [ncbi taxid: 64034]
  9. Actaea simplex [ncbi taxid: 64042]
  10. Agastache rugosa [ncbi taxid: 39271]
  11. Akebia quinata [ncbi taxid: 13331]
  12. Akebia trifoliata [ncbi taxid: 155132]
  13. Alpinia galanga [ncbi taxid: 94327]
  14. Anaxyrus americanus [ncbi taxid: 8389]
  15. Anemopsis californica [ncbi taxid: 108407]
  16. Angelica acutiloba [ncbi taxid: 55605]
  17. Angelica gigas [ncbi taxid: 85712]
  18. Angelica sinensis [ncbi taxid: 165353]
  19. Anisocycla jollyana [ncbi taxid: 3021357]
  20. Apocynum androsaemifolium [ncbi taxid: 61254]
  21. Ardisia arborescens [ncbi taxid: ]
  22. Arnebia euchroma [ncbi taxid: 373122]
  23. Arnebia guttata [ncbi taxid: 419289]
  24. Aromia moschata [ncbi taxid: 1265417]
  25. Artemisia arborescens [ncbi taxid: 72386]
  26. Artemisia argyi [ncbi taxid: 259893]
  27. Artemisia capillaries [ncbi taxid: ]
  28. Artemisia capillaris [ncbi taxid: 265783]
  29. Artemisia coerulescens [ncbi taxid: ]
  30. Artemisia dracunculus [ncbi taxid: 72341]
  31. Asarum europaeum L. [ncbi taxid: ]
  32. Asarum heterotropoides [ncbi taxid: 366663]
  33. Asarum heterotropoides f. schm. var. mandshuricum (maxim.) kitag. [ncbi taxid: ]
  34. Asarum heterotropoides var. mandshuricum [ncbi taxid: 366665]
  35. Asarum sieboldii [ncbi taxid: 76098]
  36. Asiasarum heterotropoides [ncbi taxid: ]
  37. Asiasarum sieboldii [ncbi taxid: ]
  38. Aulacomnium palustre [ncbi taxid: 171833]
  39. Berberis heterobotrys [ncbi taxid: ]
  40. Brassica hirta [ncbi taxid: ]
  41. Bruguiera gymnorhiza [ncbi taxid: 39984]
  42. Cacia concinna [ncbi taxid: ]
  43. Caesalpinia bonducella [ncbi taxid: ]
  44. Callitris columellaris [ncbi taxid: 214225]
  45. Carduus getulus [ncbi taxid: 3042177]
  46. Caulis perillae [ncbi taxid: ]
  47. Caulis perillae frutescentis [ncbi taxid: ]
  48. Cicer songoricum [ncbi taxid: ]
  49. Cimicifuga foetida [ncbi taxid: ]
  50. Cinamomum cassia [ncbi taxid: ]
  51. Cinnamomum aromaticum [ncbi taxid: 119260]
  52. Cistus creticus [ncbi taxid: 191224]
  53. Citrus limon [ncbi taxid: ]
  54. Cladonia floerkeana [ncbi taxid: 195765]
  55. Clematis chinensis [ncbi taxid: 748693]
  56. Cnidium officinale [ncbi taxid: ]
  57. Comus officinalis [ncbi taxid: ]
  58. Coptis omeiensis [ncbi taxid: 261451]
  59. Cornus officinalis [ncbi taxid: 16906]
  60. Croton nepetaefolius [ncbi taxid: ]
  61. Dacrydium franklinii [ncbi taxid: ]
  62. Daucus carota [ncbi taxid: 4039]
  63. Daucus carota subsp. sativus (Hoffm.) Schuebl. & G. Martens [ncbi taxid: ]
  64. Desmos chinensis [ncbi taxid: 1179221]
  65. Diosma acmaephylla [ncbi taxid: ]
  66. Dysoxylum hainanense [ncbi taxid: ]
  67. Ekebergia benguelensis [ncbi taxid: 2984687]
  68. Elettaria cardamomum [ncbi taxid: 105181]
  69. Elsholtzia ciliata [ncbi taxid: 662901]
  70. Elsholtzia splendens [ncbi taxid: 475396]
  71. Eremophila longifolia [ncbi taxid: 2528947]
  72. Espeletia grandiflora [ncbi taxid: 1933532]
  73. Eucalyptus hybrid [ncbi taxid: ]
  74. Fructus amomi [ncbi taxid: ]
  75. Fructus amomi rotundus [ncbi taxid: ]
  76. Fructus galangae [ncbi taxid: ]
  77. Garcinia oligantha [ncbi taxid: ]
  78. Gentiana kurroo [ncbi taxid: 1523243]
  79. Gerbera saxatilis [ncbi taxid: ]
  80. Glehnia littoralis [ncbi taxid: 48119]
  81. Glycyrrhiza foetida [ncbi taxid: 512625]
  82. Herba artemisiae scopariae [ncbi taxid: ]
  83. Hericium erinaceus [ncbi taxid: 91752]
  84. Homo sapiens [ncbi taxid: 9606]
  85. Hyacinthus orientalis [ncbi taxid: 82025]
  86. Hyssopus officinalis [ncbi taxid: ]
  87. Hyssopus officinalis L. [ncbi taxid: ]
  88. Illicium difengpi [ncbi taxid: 124772]
  89. Indigofera carlesii [ncbi taxid: 595571]
  90. Inula germanica [ncbi taxid: 313945]
  91. Iris spuria [ncbi taxid: 93026]
  92. Isatis tinctoria [ncbi taxid: 161756]
  93. Lagascea mollis [ncbi taxid: 1475413]
  94. Laurencia irieii [ncbi taxid: ]
  95. Laurus nobilis [ncbi taxid: 85223]
  96. Laurus nobilis L. [ncbi taxid: ]
  97. Leptosyne stillmanii [ncbi taxid: 159684]
  98. Licaria puchuri-major [ncbi taxid: ]
  99. Ligusticum chuanxiong [ncbi taxid: 2689076]
  100. Ligusticum sinense [ncbi taxid: ]
  101. Lithospermum erythrorhizon [ncbi taxid: 34254]
  102. Magnolia liliflora [ncbi taxid: ]
  103. Magnolia liliiflora [ncbi taxid: 3403]
  104. Magnolia salicifolia [ncbi taxid: 3411]
  105. Melaleuca leucadendra [ncbi taxid: 164936]
  106. Melicertus plebejus [ncbi taxid: ]
  107. Michelia alba [ncbi taxid: ]
  108. Monopterix uaucu [ncbi taxid: ]
  109. Mosla chinensis [ncbi taxid: 516065]
  110. Myristica fragrans [ncbi taxid: 51089]
  111. Myrrhis odorata (L.) Scop. [ncbi taxid: ]
  112. Myrtus communis [ncbi taxid: 119949]
  113. Nectandra polita [ncbi taxid: ]
  114. Nierembergia aristata [ncbi taxid: 274371]
  115. Ocimum basilicum [ncbi taxid: 39350]
  116. Ocimum basilicum L. [ncbi taxid: ]
  117. Ocimum gratissimum [ncbi taxid: 204144]
  118. Ocotea pretiosa [ncbi taxid: ]
  119. Pagrus major [ncbi taxid: 143350]
  120. Parmelia vittata [ncbi taxid: ]
  121. Pericarpium zanthoxyli [ncbi taxid: ]
  122. Phlegmariurus yunnanensis [ncbi taxid: 385391]
  123. Phyllanthus emblica [ncbi taxid: ]
  124. Phyllospongia papyracea [ncbi taxid: 279625]
  125. Pimenta dioica [ncbi taxid: 375272]
  126. Pinellia ternata [ncbi taxid: 199225]
  127. Pinus nigra J. F. Arnold [ncbi taxid: ]
  128. Pinus sylvestris [ncbi taxid: 3349]
  129. Pinus sylvestris L. [ncbi taxid: ]
  130. Piper betle [ncbi taxid: 13217]
  131. Piper sanctum [ncbi taxid: 511552]
  132. Pisolithus arhizus [ncbi taxid: 80664]
  133. Pocillopora damicornis [ncbi taxid: 46731]
  134. Podocarpus ferruginea [ncbi taxid: ]
  135. Polygala sibirica [ncbi taxid: 690825]
  136. Polygala tenuifolia [ncbi taxid: 355332]
  137. Protaetia cuprea [ncbi taxid: 360077]
  138. Pulmonaria mollis [ncbi taxid: 256500]
  139. Radix chuanxiong [ncbi taxid: ]
  140. Radix smilacis [ncbi taxid: ]
  141. Rhizoma arisaema cum bile [ncbi taxid: ]
  142. Rhizoma chuanxiong [ncbi taxid: ]
  143. Rosa multiflora [ncbi taxid: 74647]
  144. Rosa rugosa [ncbi taxid: 74645]
  145. Rosmarinus officinalis [ncbi taxid: ]
  146. Rubus trifidus [ncbi taxid: 75096]
  147. Satureja montana [ncbi taxid: 49988]
  148. Satureja montana L. [ncbi taxid: ]
  149. Scutellaria barbata [ncbi taxid: 396367]
  150. Sophora flavescens [ncbi taxid: 49840]
  151. Stolonica socialis [ncbi taxid: 581074]
  152. Sus scrofa [ncbi taxid: 9823]
  153. Syzygium aromaticum [ncbi taxid: 219868]
  154. Talaromyces islandicus [ncbi taxid: 28573]
  155. Tephrosia crassifolia [ncbi taxid: 3091980]
  156. Tetracera alnifolia [ncbi taxid: ]
  157. Zanthoxylum bungeanum [ncbi taxid: 328401]
  158. Zingiber cassumunar Roxb. [ncbi taxid: ]
  159. Zingiber officinale [ncbi taxid: 94328]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:SORGHUMBICOLOR_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:CANNUUM_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:CARIETINUM_ICC4958_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:CARROT_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:CSATIVA_PK_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:MUSKMELON_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:LJAPONICUS_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:WHEATD_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:DROTUNDATA_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:POPLAR_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:BAMBARABEAN_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:BANANA_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:TOMATO_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:DATEPALM_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:OTHOMAEUM_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:PLANT_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:CASHEW_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:SOY_PWY-4201 volatile cinnamoic ester biosynthesis
PlantCyc:REDSAGE_PWY-4201 volatile cinnamoic ester biosynthesis
View All Pathways