Aromatic primary alcohol (BioCAD00000006795)

plant natural products microbial natural products

Metabolite Card

Formula: C7H8O (108.0575)
SMILES: OCC1=CC=CC=C1

Synonyms [en]

Phenylcarbinol; Benzenemethanol; benzyl alcohol; phenylmethanol; Aromatic alcohol; alcoholum benzylicum

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Aromatic primary alcohol. 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: BioCAD00000006795). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Benzyl alcohol is a colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with Lidocaine injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutical aid, and in perfumery and flavoring. Benzyl Alcohol is an aromatic alcohol used in a wide variety of cosmetic formulations as a fragrance component, preservative, solvent, and viscosity-decreasing agent. Benzyl alcohol is metabolized to Benzoic Acid, which reacts with glycine and excreted as hippuric acid in the human body. Acceptable daily intakes were established by the World Health Organization at 5 mg/kg for Benzyl alcohol. No adverse effects of benzyl alcohol have been seen in chronic exposure animal studies using rats and mice. Effects of Benzyl Alcohol in chronic exposure animal studies are limited to reduced feed intake and reduced growth. Some differences have been noted in one reproductive toxicity study using mice, but these were limited to lower maternal body weights and decreased mean litter weights. Another study also noted that fetal weight was decreased compared to controls, but a third study showed no differences between control and benzyl alcohol-treated groups. Benzyl alcohol has been associated with an increased number of resorptions and malformations in hamsters, but there have been no reproductive or developmental toxicity findings in studies using mice and rats. Genotoxicity tests for benzyl alcohol are mostly negative, but there were some assays that were positive. Carcinogenicity studies, however, were negative. Clinical data indicates that benzyl alcohol can produce nonimmunologic contact urticaria and nonimmunologic immediate contact reactions, characterized by the appearance of wheals, erythema, and pruritis. 5% benzyl alcohol can elicit a reaction. Benzyl alcohol is not a sensitizer at 10%. Benzyl alcohol could be used safely at concentrations up to 5%, but that manufacturers should consider the nonimmunologic phenomena when using benzyl alcohol in cosmetic formulations designed for infants and children. Additionally, Benzyl alcohol is considered safe up to 10% for use in hair dyes. The limited body exposure, the duration of use, and the frequency of use are considered in concluding that the nonimmunologic reactions would not be a concern. Because of the wide variety of product types in which benzyl alcohol may be used, it is likely that inhalation may be a route of exposure. The available safety tests are not considered sufficient to support the safety of benzyl alcohol in formulations where inhalation is a route of exposure. Inhalation toxicity data are needed to complete the safety assessment of benzyl alcohol where inhalation can occur. (PMID:11766131).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 100-51-6
  • CAS Registry Number: 185532-71-2
  • CAS Registry Number: 201740-95-6
  • CAS Registry Number: 66072-40-0
  • PubChem: 244
  • ChEBI: ChEBI:17987
  • HMDB: HMDB0003119
  • KEGG: C03485
  • BioCyc: BENZYL-ALCOHOL
  • Wikipedia: Benzyl_Alcohol
  • DrugBank: DB06770
  • Coconut NaturalProduct: CNP0263608.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01487 1.1.1.90 aromatic alcohol:NAD+ oxidoreductase
KEGG:R01488 1.1.1.91 aromatic alcohol:NADP+ oxidoreductase
KEGG:R01491 1.1.3.7 aromatic alcohol:oxygen oxidoreductase
Rhea:RHEA:18902 3.5.1.64 N-benzyloxycarbonyl-L-leucine + H2O + H+ => benzyl alcohol + L-leucine + CO2
Rhea:RHEA:18903 3.5.1.64 benzyl alcohol + L-leucine + CO2 => N-benzyloxycarbonyl-L-leucine + H2O + H+
Rhea:RHEA:18904 3.5.1.64 N-benzyloxycarbonyl-L-leucine + H2O + H+ <=> benzyl alcohol + L-leucine + CO2
Rhea:RHEA:20901 3.5.1.58 N-benzyloxycarbonylglycine + H2O + H+ => benzyl alcohol + glycine + CO2
Rhea:RHEA:20902 3.5.1.58 benzyl alcohol + glycine + CO2 => N-benzyloxycarbonylglycine + H2O + H+
Rhea:RHEA:20903 3.5.1.58 N-benzyloxycarbonylglycine + H2O + H+ <=> benzyl alcohol + glycine + CO2
Rhea:RHEA:23461 3.1.1.70 benzyl cetraxate + H2O => cetraxate + benzyl alcohol + H+
Rhea:RHEA:23462 3.1.1.70 cetraxate + benzyl alcohol + H+ => benzyl cetraxate + H2O
Rhea:RHEA:23463 3.1.1.70 benzyl cetraxate + H2O <=> cetraxate + benzyl alcohol + H+
Rhea:RHEA:30412 2.3.1.196 benzyl alcohol + benzoyl-CoA => benzyl benzoate + CoA
Rhea:RHEA:30413 2.3.1.196 benzyl benzoate + CoA => benzyl alcohol + benzoyl-CoA
Rhea:RHEA:30414 2.3.1.196 benzyl alcohol + benzoyl-CoA <=> benzyl benzoate + CoA
Rhea:RHEA:36148 2.3.1.224 benzyl alcohol + acetyl-CoA => benzyl acetate + CoA
Rhea:RHEA:36149 2.3.1.224 benzyl acetate + CoA => benzyl alcohol + acetyl-CoA
Rhea:RHEA:36150 2.3.1.224 benzyl alcohol + acetyl-CoA <=> benzyl acetate + CoA
Rhea:RHEA:51593 1.14.15.26 toluene + 2 reduced [2Fe-2S]-[ferredoxin] + O2 + 2 H+ => benzyl alcohol + 2 oxidized [2Fe-2S]-[ferredoxin] + H2O
Rhea:RHEA:51594 1.14.15.26 benzyl alcohol + 2 oxidized [2Fe-2S]-[ferredoxin] + H2O => toluene + 2 reduced [2Fe-2S]-[ferredoxin] + O2 + 2 H+
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Organism Source

Taxonomy Source

  1. Acacia aulacocarpa [ncbi taxid: 138511]
  2. Acacia longifolia [ncbi taxid: 139010]
  3. Aceriphyllum rossii [ncbi taxid: ]
  4. Actaea dahurica [ncbi taxid: 64029]
  5. Actaea heracleifolia [ncbi taxid: 64034]
  6. Actaea simplex [ncbi taxid: 64042]
  7. Agnorhiza bolanderi [ncbi taxid: 230216]
  8. Alangium premnifolium [ncbi taxid: 2918396]
  9. Albizia coriaria [ncbi taxid: 2708711]
  10. Alligator mississippiensis [ncbi taxid: 8496]
  11. Aloe africana [ncbi taxid: 1080010]
  12. Aloe ferox [ncbi taxid: 117798]
  13. Aloe spicata [ncbi taxid: 992642]
  14. Aloe vera [ncbi taxid: 34199]
  15. Anaxagorea clavata [ncbi taxid: ]
  16. Anemone flaccida [ncbi taxid: ]
  17. Angelica anomala [ncbi taxid: 357845]
  18. Angelica tarokoensis [ncbi taxid: 2831630]
  19. Araujia sericifera [ncbi taxid: 63463]
  20. Ardisia neriifolia [ncbi taxid: 2184479]
  21. Aria pallescens [ncbi taxid: ]
  22. Arnica nevadensis [ncbi taxid: 436208]
  23. Artemisia argyi [ncbi taxid: 259893]
  24. Artemisia monogyna [ncbi taxid: 1903222]
  25. Artemisia montana [ncbi taxid: 669134]
  26. Artemisia princeps [ncbi taxid: 223870]
  27. Aspidosperma subincanum [ncbi taxid: 2743209]
  28. Astragalus canadensis [ncbi taxid: 20408]
  29. Bassia butyracea [ncbi taxid: ]
  30. Beyeria brevifolia [ncbi taxid: 2752376]
  31. Bistorta manshuriensis [ncbi taxid: 1548133]
  32. Bistorta officinalis [ncbi taxid: 125587]
  33. Bombax ceiba [ncbi taxid: 45325]
  34. Bragantia wallichii [ncbi taxid: ]
  35. Bursaria spinosa [ncbi taxid: 105281]
  36. Chloranthus tianmushanensis [ncbi taxid: ]
  37. Chromolaena odorata [ncbi taxid: 103745]
  38. Chromolaena pulchella [ncbi taxid: ]
  39. Cimicifuga foetida [ncbi taxid: ]
  40. Cinamomum cassia [ncbi taxid: ]
  41. Cinnamomum aromaticum [ncbi taxid: 119260]
  42. Citrullus lanatus [ncbi taxid: 3654]
  43. Citrus reticulata [ncbi taxid: 85571]
  44. Citrus reticulate [ncbi taxid: ]
  45. Cladonia evansii [ncbi taxid: 197026]
  46. Clonostachys rosea [ncbi taxid: 29856]
  47. Cnidium officinale [ncbi taxid: ]
  48. Coccus fagi [ncbi taxid: ]
  49. Colobocentrotus atratus [ncbi taxid: 39290]
  50. Craibiodendron yunnanese [ncbi taxid: ]
  51. Crocus sativus [ncbi taxid: 82528]
  52. Cryptocarya aschersoniana [ncbi taxid: 1345236]
  53. Delphinium andersoni [ncbi taxid: ]
  54. Dendrosenecio kilimanjari [ncbi taxid: 109559]
  55. Dianthus caryophyllus L. [ncbi taxid: ]
  56. Dioecrescis erythroclada [ncbi taxid: 1571008]
  57. Diphasia angolensis [ncbi taxid: ]
  58. Dipterocarpus alatus [ncbi taxid: 340438]
  59. Drosera peltata [ncbi taxid: 4369]
  60. Echinops amplexicaulis [ncbi taxid: 910522]
  61. Elysia rufescens [ncbi taxid: 380559]
  62. Epaltes gariepina [ncbi taxid: 1548596]
  63. Epimedium davidii [ncbi taxid: 253605]
  64. Erysimum odoratum [ncbi taxid: 1137569]
  65. Eucalyptus melliodora [ncbi taxid: 183838]
  66. Eupatorium argentinum [ncbi taxid: ]
  67. Eupolyphaga sinensis [ncbi taxid: 367774]
  68. Eutypella scoparia [ncbi taxid: ]
  69. Ficus formosana [ncbi taxid: 1127366]
  70. Frullania tamarisci [ncbi taxid: 95764]
  71. Fusarium gibbosum [ncbi taxid: 2126134]
  72. Galenia africana [ncbi taxid: ]
  73. Gardenia fosbergii [ncbi taxid: ]
  74. Gastrodia elata [ncbi taxid: 91201]
  75. Globba malaccensis [ncbi taxid: ]
  76. Gnidia lamprantha [ncbi taxid: ]
  77. Guatteria boliviana [ncbi taxid: 343271]
  78. Hesperis matronalis [ncbi taxid: 264418]
  79. Heterotheca inuloides [ncbi taxid: 3015714]
  80. Homo sapiens [ncbi taxid: 9606]
  81. Hyssopus officinalis [ncbi taxid: ]
  82. Ilex affinis [ncbi taxid: 185489]
  83. Ilex amara [ncbi taxid: 185490]
  84. Illicium verum [ncbi taxid: 124778]
  85. Isodon japonicus [ncbi taxid: 425908]
  86. Isodon kameba [ncbi taxid: ]
  87. Juniperus brevifolia [ncbi taxid: 746017]
  88. Kaempferia pulchra [ncbi taxid: 199647]
  89. Knightia excelsa [ncbi taxid: 35944]
  90. Lactarius scrobiculatus [ncbi taxid: 93011]
  91. Laurencia distichophylla [ncbi taxid: ]
  92. Leonurus glaucescens [ncbi taxid: 445399]
  93. Lepidium draba [ncbi taxid: 153317]
  94. Levisticum officinale [ncbi taxid: 48042]
  95. Ligusticum sinense [ncbi taxid: ]
  96. Liquidambar orientalis [ncbi taxid: 63360]
  97. Liriope muscari [ncbi taxid: 39529]
  98. Lonicera japonica [ncbi taxid: 105884]
  99. Maba buxifolia [ncbi taxid: ]
  100. Mentha x piperita [ncbi taxid: 34256]
  101. Micromeria pineolens [ncbi taxid: 306397]
  102. Morus alba [ncbi taxid: 3498]
  103. Morus bombycis [ncbi taxid: 66393]
  104. Nemalion vermiculare [ncbi taxid: 935621]
  105. Neolentinus lepideus [ncbi taxid: 38799]
  106. Nidula candida [ncbi taxid: 1348642]
  107. Odixia angusta [ncbi taxid: 125740]
  108. Ophiocoma scolopendrina [ncbi taxid: 1365868]
  109. Ophiopogon japonicus [ncbi taxid: 100506]
  110. Osmanthus fragrans [ncbi taxid: 93977]
  111. Penicillium citreonigrum [ncbi taxid: 69768]
  112. Peritassa compta [ncbi taxid: ]
  113. Petiveria alliacea [ncbi taxid: 46142]
  114. Pheidole pallidula [ncbi taxid: 190770]
  115. Pogostemon cablin [ncbi taxid: 28511]
  116. Prosopis glandulosa [ncbi taxid: ]
  117. Proteaceae [ncbi taxid: 4328]
  118. Prunus laurocerasus [ncbi taxid: 32242]
  119. Prunus mume [ncbi taxid: 102107]
  120. Pseudopterogorgia kallos [ncbi taxid: ]
  121. Psiadia dentata [ncbi taxid: 1225829]
  122. Pteris prolifera [ncbi taxid: ]
  123. Pterocarpus grandiflorus [ncbi taxid: ]
  124. Pyrosoma giganteum [ncbi taxid: ]
  125. Quercus aegilops [ncbi taxid: ]
  126. Quercus sessiliflora [ncbi taxid: ]
  127. Rheedia acuminata [ncbi taxid: ]
  128. Rhizobium phaseoli [ncbi taxid: 396]
  129. Rosmarinus officinalis [ncbi taxid: ]
  130. Salacia madagascariensis [ncbi taxid: 670374]
  131. Salvia officinalis [ncbi taxid: 38868]
  132. Saussurea carthamoides [ncbi taxid: ]
  133. Saxifraga stolonifera [ncbi taxid: 182070]
  134. Saxifraga stolonifera Meerb. [ncbi taxid: ]
  135. Securidaca inappendiculata [ncbi taxid: 3091905]
  136. Senecio squalidus [ncbi taxid: 121554]
  137. Seriphidium cinum [ncbi taxid: ]
  138. Serratia odorifera [ncbi taxid: 618]
  139. Sesbania punicea [ncbi taxid: 543741]
  140. Simira eliezeriana [ncbi taxid: ]
  141. Solanum acaule [ncbi taxid: 103871]
  142. Spodoptera eridania [ncbi taxid: 37547]
  143. Stenostomum lucidum [ncbi taxid: 43446]
  144. Stevia amambayensis [ncbi taxid: ]
  145. Streptomyces althioticus [ncbi taxid: 83380]
  146. Streptomyces ANU 6277 [ncbi taxid: ]
  147. Streptomyces griseovariabilis [ncbi taxid: 284636]
  148. Swertia delavayi [ncbi taxid: 166617]
  149. Swertia hickinii [ncbi taxid: ]
  150. Symphyocladia latiuscula [ncbi taxid: 396806]
  151. Syzygium aromaticum [ncbi taxid: 219868]
  152. Tacca esquirolii [ncbi taxid: ]
  153. Taxodium mucronatum [ncbi taxid: 99812]
  154. Trichosanthes kirilowii [ncbi taxid: 3677]
  155. Vaccinium corymbosum [ncbi taxid: 69266]
  156. Vaccinium myrtillus [ncbi taxid: 180763]
  157. Vaccinium vitis-idaea [ncbi taxid: 180772]
  158. Vallota purpurea [ncbi taxid: ]
  159. Vismia jefensis [ncbi taxid: ]
  160. Vitex madiensis [ncbi taxid: 1899206]

Pathway Synthetic

pathway id name
BioCyc:META_TOLUENE-DEG-CATECHOL-PWY toluene degradation to benzoate
BioCyc:META_PWY-5178 toluene degradation IV (aerobic) (via catechol)
BioCyc:META_PWY-5183 superpathway of aerobic toluene degradation
BioCyc:META_PWY-7114 tea aroma glycosidic precursor bioactivation
BioCyc:META_PWY-6801 volatile esters biosynthesis (during fruit ripening)
BioCyc:ECO_TRNA-CHARGING-PWY tRNA charging
BioCyc:ARA_PWY-4203 volatile benzenoid biosynthesis I (ester formation)
BioCyc:ARA_PWY-6443 benzoate biosynthesis I (CoA-dependent, β-oxidative)
BioCyc:META_PWY-4203 volatile benzenoid biosynthesis I (ester formation)
BioCyc:META_PWY-6443 benzoate biosynthesis I (CoA-dependent, β-oxidative)
BioCyc:META_PWY-6766 salicin biosynthesis
BioCyc:SCO_TOLUENE-DEG-CATECHOL-PWY toluene degradation to benzoate
BioCyc:META_PWY-6763 salicortin biosynthesis
BioCyc:META_TRNA-CHARGING-PWY tRNA charging
BioCyc:META_PWY-6011 amygdalin and prunasin degradation
BioCyc:META_PWY-5184 toluene degradation VI (anaerobic)
BioCyc:META_PWY-81 toluene degradation to benzoyl-CoA (anaerobic)
PathBank:SMP0000854 Hexuronide and Hexuronate Degradation
PathBank:SMP0000932 Glycerol Metabolism II
PathBank:SMP0000933 Glycerol Metabolism III (sn-Glycero-3-Phosphoethanolamine)
View All Pathways