Safrole (BioCAD00000017496)

plant natural products microbial natural products

Metabolite Card

Formula: C10H10O2 (162.0681)
SMILES: C=CCC1=CC2=C(OCO2)C=C1

Synonyms [en]

safrole; Shikimole; Safrol; 5-Allyl-1,3-benzodioxole; m-Allylpyrocatechin methylene ether; 5-(2-Propenyl)-1,3-benzodioxole

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Safrole. 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: BioCAD00000017496). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Safrole, also known as shikimol, is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil, or synthesized from other related methylenedioxy compounds. It is the principal component of brown camphor oil, and is found in small amounts in a wide variety of plants, where it functions as a natural pesticide. Safrole is found in anise and nutmeg. Banned by FDA for use in food. Safrole is formerly used as a food flavour It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide and the recreational drug MDMA ("Ecstacy"). Safrole is a natural plant constituent, found in oil of sassafras and certain other essential oils. It is a member of the methylenedioxybenzene group of compounds, many of which (e.g. piperonyl butoxide) are extensively used as insecticide synergists. Safrole is a major source of human exposure to safrole is through consumption of spices, such as nutmeg, cinnamon and black pepper, in which safrole is a constituent. Safrole is also present in root beer, and has been used as an additive in chewing gum, toothpaste, soaps and certain pharmaceutical preparations. Safrole is a weak hepatocarcinogen and it is a matter of considerable interest whether the ally1 moiety or the methylenedioxy group, or both, are involved in the mechanism of its carcinogenesis. Safrole is extensively metabolized, giving rise to a large number of metabolites. Metabolism involves essentially two major routes, oxidation of the ally1 side chain, and oxidation of the methylenedioxy group with subsequent cleavage to form the catechol. Safrole undergoes oxidation of the allylic group to yield the 2, 3-epoxide (safrole epoxide). The dihydrodiol is one of the metabolites of safrole, and presumably arises from the hydration of the 2, 3-epoxide. The principal route of metabolism of safrole is through cleavage of the methylenedioxy group, the major metabolites being allylcatechol and its isomer, propenylcatechol. Eugenol and its isomer I-methoxy- 2-hydroxy-4-allylbenzene have been detected as minor metabolites in rat, mouse and human (PMID:6719936). The Ocotea cymbarum oil made of the Ocotea pretiosa, a plant growing in Brazil, and sassafras oil made of Sassafras albidum, a tree growing in eastern North America, are the main natural sources for safrole. It has a characteristic "candy-shop" aroma

Cytoplasm Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 1126-61-0
  • CAS Registry Number: 8006-80-2
  • CAS Registry Number: 94-59-7
  • PubChem: 5144
  • ChEBI: ChEBI:8994
  • HMDB: HMDB0033591
  • KEGG: C10490
  • BioCyc: CPD-21978
  • NCBI MeSH: Safrole
  • Wikipedia: Safrole
  • RefMet: RM0136667
  • MoNA: Bruker_HCD_library001022
  • MoNA: HMDB0033591_c_ms_101347
  • MoNA: HMDB0033591_c_ms_101348
  • MoNA: HMDB0033591_c_ms_101349
  • MoNA: HMDB0033591_c_ms_101350
  • MoNA: HMDB0033591_c_ms_101351
  • MoNA: JP005804
  • MoNA: JP009330
  • MoNA: JP009448
  • MoNA: JP009742
  • Metlin: METLIN_44059
  • Coconut NaturalProduct: CNP0320423.0
  • Coconut NaturalProduct: CNP0508090.0

Class / Ontology

Metabolic Network
ID EC Number Name
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Organism Source

Taxonomy Source

  1. Acanthopanax ricinifolius [ncbi taxid: ]
  2. Aconitum episcopale [ncbi taxid: 226106]
  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. Actinomadura hibisca [ncbi taxid: 68565]
  8. Agave lophantha [ncbi taxid: ]
  9. Albizia Julibrissin [ncbi taxid: 3813]
  10. Anacardium occidentale [ncbi taxid: 171929]
  11. Anastrepha suspensa [ncbi taxid: 28587]
  12. Anchusa officinalis [ncbi taxid: 89630]
  13. Andinobates fulguritus [ncbi taxid: 111124]
  14. Anethum graveolens [ncbi taxid: 40922]
  15. Angelica acutiloba [ncbi taxid: 55605]
  16. Angelica gigas [ncbi taxid: 85712]
  17. Angelica sinensis [ncbi taxid: 165353]
  18. Aniba spp. [ncbi taxid: ]
  19. Ardisia arborescens [ncbi taxid: ]
  20. Aromia moschata [ncbi taxid: 1265417]
  21. Artemisia dracunculus [ncbi taxid: 72341]
  22. Artemisia glutinosa [ncbi taxid: ]
  23. Asarum forbesii [ncbi taxid: 76091]
  24. Asarum heterotropoides [ncbi taxid: 366663]
  25. Asarum heterotropoides f. schm. var. mandshuricum (maxim.) kitag. [ncbi taxid: ]
  26. Asarum heterotropoides var.mandshuricum [ncbi taxid: ]
  27. Asarum sieboldii [ncbi taxid: 76098]
  28. Asiasarum heterotropoides [ncbi taxid: ]
  29. Asiasarum sieboldii [ncbi taxid: ]
  30. Aspergillus caespitosus [ncbi taxid: 176165]
  31. Astilbe koreana [ncbi taxid: 657399]
  32. Boronia muelleri [ncbi taxid: 1764345]
  33. Bothriospermum secundum [ncbi taxid: 1421720]
  34. Bowdichia nitida [ncbi taxid: 595543]
  35. Burkholderia cepacia [ncbi taxid: 292]
  36. Cacia concinna [ncbi taxid: ]
  37. Calocera viscosa [ncbi taxid: 63146]
  38. Cardium corbis [ncbi taxid: ]
  39. Caryocar glabrum [ncbi taxid: 72385]
  40. Caryopteris mongholica [ncbi taxid: 201515]
  41. Cassia carnaval [ncbi taxid: ]
  42. Catalpa bignonioides [ncbi taxid: 85179]
  43. Cephalonoplos segetum [ncbi taxid: 41543]
  44. Cinamomum cassia [ncbi taxid: ]
  45. Cinnamomum aromaticum [ncbi taxid: 119260]
  46. Cinnamomum camphora [ncbi taxid: 13429]
  47. Cinnamomum micranthum [ncbi taxid: 337465]
  48. Citrus aurantium [ncbi taxid: ]
  49. Citrus natsudaidai [ncbi taxid: 109792]
  50. Citrus sinensis [ncbi taxid: 2711]
  51. Citrus trifoliata [ncbi taxid: 37690]
  52. Colchicum macedonicum [ncbi taxid: 225786]
  53. Comaster multifida [ncbi taxid: ]
  54. Conoideocrella tenuis [ncbi taxid: 1105321]
  55. Coprosma acerosa [ncbi taxid: 225357]
  56. Coptis deltoidea [ncbi taxid: 261449]
  57. Coptis omeiensis [ncbi taxid: 261451]
  58. Cranfillia vulcanica [ncbi taxid: 393586]
  59. Curcuma amanda Roxb [ncbi taxid: ]
  60. Cyanospira rippkae [ncbi taxid: ]
  61. Cymathere triplicata [ncbi taxid: ]
  62. Dalbergia frutescens [ncbi taxid: 450026]
  63. Dalbergia rubiginosa [ncbi taxid: 1635142]
  64. Dicliptera riparia [ncbi taxid: ]
  65. Dillenia papuana [ncbi taxid: 1085409]
  66. Diosma acmaephylla [ncbi taxid: ]
  67. Elaeagnus umbellata [ncbi taxid: 43233]
  68. Elsholtzia ciliata [ncbi taxid: 662901]
  69. Eremophila longifolia [ncbi taxid: 2528947]
  70. Erwinia rhapontici [ncbi taxid: 55212]
  71. Esenbeckia nesiotica [ncbi taxid: ]
  72. Eucalyptus citriodora [ncbi taxid: ]
  73. Eucalyptus hybrid [ncbi taxid: ]
  74. Euphorbia caducifolia [ncbi taxid: 1129975]
  75. Euphorbia kansui [ncbi taxid: 239687]
  76. Ficus elastica [ncbi taxid: 182112]
  77. Forsythia suspensa [ncbi taxid: 126418]
  78. Forsythia suspense [ncbi taxid: ]
  79. Garcinia oligantha [ncbi taxid: ]
  80. Gibberella saubinetii [ncbi taxid: ]
  81. Helianthopsis bishopii [ncbi taxid: ]
  82. Helipterum tenellum [ncbi taxid: ]
  83. Hypericum papuanum [ncbi taxid: 1137007]
  84. Hypselodoris cantabrica [ncbi taxid: ]
  85. Hyptis tomentosa [ncbi taxid: ]
  86. Ilex kaushue [ncbi taxid: 1006183]
  87. Illicium difengpi [ncbi taxid: 124772]
  88. Illicium religiosum [ncbi taxid: ]
  89. Illicium verum [ncbi taxid: 124778]
  90. Inula germanica [ncbi taxid: 313945]
  91. Inula thapsoides [ncbi taxid: ]
  92. Ipomoea cristulata [ncbi taxid: 1917418]
  93. Iris spuria [ncbi taxid: 93026]
  94. Juniperus scopulorum [ncbi taxid: 466205]
  95. Kaunia arbuscularis [ncbi taxid: ]
  96. Lachnoanaerobaculum saburreum [ncbi taxid: 467210]
  97. Laurencia irieii [ncbi taxid: ]
  98. Lens phaseoloides [ncbi taxid: ]
  99. Leptolobium panamense [ncbi taxid: 100136]
  100. Leucetta microrhaphis [ncbi taxid: ]
  101. Leucophyllum ambiguum [ncbi taxid: 1382326]
  102. Licaria puchuri-major [ncbi taxid: ]
  103. Licaria puchury-major [ncbi taxid: ]
  104. Limeum pterocarpum [ncbi taxid: 764827]
  105. Litsea cubeba [ncbi taxid: 155299]
  106. Lophozonia menziesii [ncbi taxid: ]
  107. Lupinus formosus [ncbi taxid: 53227]
  108. Macrocystidia cucumis [ncbi taxid: 182055]
  109. Magnolia salicifolia [ncbi taxid: 3411]
  110. Malaxis grandifolia [ncbi taxid: ]
  111. Mappia foetida [ncbi taxid: 487070]
  112. Melicope indica [ncbi taxid: ]
  113. Mesembryanthemum tortuosum [ncbi taxid: 216016]
  114. Metapenaeus macleayi [ncbi taxid: 578590]
  115. Monomorium delagoense [ncbi taxid: ]
  116. Morchella vulgaris [ncbi taxid: 60348]
  117. Mosla chinensis [ncbi taxid: 516065]
  118. Myristica fragrans [ncbi taxid: 51089]
  119. Nectandra polita [ncbi taxid: ]
  120. Nemuaron humboldtii [ncbi taxid: ]
  121. Nerita albicilla [ncbi taxid: 52928]
  122. Ocimum basilicum [ncbi taxid: 39350]
  123. Ocimum basilicum L. [ncbi taxid: ]
  124. Ocotea pretiosa [ncbi taxid: ]
  125. Oxandra xylopioides [ncbi taxid: 306934]
  126. Pagrus major [ncbi taxid: 143350]
  127. Palicourea alpina [ncbi taxid: 60103]
  128. Pancratium trianthum [ncbi taxid: 1055008]
  129. Parmelia enteromorpha [ncbi taxid: ]
  130. Parmelia vittata [ncbi taxid: ]
  131. Persicaria thunbergii [ncbi taxid: 668956]
  132. Pinellia ternata [ncbi taxid: 199225]
  133. Piper aduncum [ncbi taxid: 130377]
  134. Piper cubeba [ncbi taxid: 405322]
  135. Piper pedicellosum [ncbi taxid: 2231266]
  136. Pocillopora damicornis [ncbi taxid: 46731]
  137. Posoqueria latifolia [ncbi taxid: 58460]
  138. Protaetia cuprea [ncbi taxid: 360077]
  139. Pyracantha angustifolia [ncbi taxid: 690342]
  140. Ramalina terebrata [ncbi taxid: 387287]
  141. Resinicium pinicola [ncbi taxid: ]
  142. Rhodomyrtus tomentosa [ncbi taxid: 98583]
  143. Rhodotypos scandens [ncbi taxid: 32245]
  144. Rosmarinus officinalis [ncbi taxid: ]
  145. Rubus trifidus [ncbi taxid: 75096]
  146. Salix sieboldiana [ncbi taxid: 2878180]
  147. Salvia xalapensis [ncbi taxid: 2039553]
  148. Sambucus ebulus [ncbi taxid: 28503]
  149. Sassafras albidum [ncbi taxid: 46945]
  150. Satureja atropatana [ncbi taxid: 2996424]
  151. Saussurea lappa [ncbi taxid: ]
  152. Scrophularia smithii [ncbi taxid: 1357656]
  153. Solanum torvum [ncbi taxid: 119830]
  154. Sonchus leptocephalus [ncbi taxid: 50223]
  155. Streptomyces fulvoviridis [ncbi taxid: 66891]
  156. Tanacetum santolinoides [ncbi taxid: ]
  157. Trifolium alexandrium [ncbi taxid: ]
  158. Trifolium pratense [ncbi taxid: 57577]
  159. Tylophora flava [ncbi taxid: ]
  160. Wunderlichia mirabilis [ncbi taxid: 375931]
  161. Xanthostemon oppositifolius [ncbi taxid: 1619564]
  162. Zilla spinosa [ncbi taxid: 127626]
  163. Zingiber officinale [ncbi taxid: 94328]
  164. Abrus pulchellus [ncbi taxid: 192852]
  165. Asarum forbesii [ncbi taxid: 76091]
  166. Asarum heterotropoides var. mandshuricum [ncbi taxid: 366665]
  167. Asarum sieboldii [ncbi taxid: 76098]
  168. Cinnamomum camphora [ncbi taxid: 13429]
  169. Crocus sativus [ncbi taxid: 82528]
  170. Elsholtzia splendens [ncbi taxid: 475396]
  171. Forsythia suspensa [ncbi taxid: 126418]
  172. Fructus amomi [ncbi taxid: ]
  173. Fructus amomi rotundus [ncbi taxid: ]
  174. Gomphrena globosa [ncbi taxid: 221775]
  175. Homo sapiens [ncbi taxid: 9606]
  176. Illicium religiosum [ncbi taxid: ]
  177. Juniperus scopulorum [ncbi taxid: 466205]
  178. Ligum cinnamomi camphorae [ncbi taxid: ]
  179. Lycium chinense [ncbi taxid: 112883]
  180. Magnolia liliflora [ncbi taxid: ]
  181. Magnolia liliiflora [ncbi taxid: 3403]
  182. Magnolia salicifolia [ncbi taxid: 3411]
  183. Myristica fragrans [ncbi taxid: 51089]
  184. Ocimum basilicum [ncbi taxid: 39350]
  185. Rhizoma arisaema cum bile [ncbi taxid: ]
  186. Sassafras albidum [ncbi taxid: 46945]
  187. Sassafras tzumu [ncbi taxid: 128701]
  188. Zingiber officinale [ncbi taxid: 94328]

Pathway Synthetic

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