Phenylacetaldehyde (BioCAD00000016161)

feces plant natural products microbial natural products

Metabolite Card

Formula: C8H8O (120.0575)
SMILES: O=CCC1=CC=CC=C1

Synonyms [en]

phenylacetaldehyde; 2-phenylacetaldehyde; alpha-Tolualdehyde; Hyacinthin; Benzeneacetaldehyde; Phenylacetic aldehyde

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Phenylacetaldehyde. 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: BioCAD00000016161). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form. (PMID: 16910727, 7818768, 15606130).

Cytoplasm
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 122-78-1
  • PubChem: 998
  • ChEBI: ChEBI:16424
  • HMDB: HMDB0006236
  • HMDB: HMDB06236
  • KEGG: C00601
  • BioCyc: PHENYLACETALDEHYDE
  • NCBI MeSH: phenylacetaldehyde
  • Wikipedia: Phenylacetaldehyde
  • DrugBank: DB02178
  • RefMet: RM0031042
  • MoNA: BAF_UVA_POS000439
  • MoNA: BAF_UVA_POS000629
  • MoNA: FiehnHILIC000673
  • MoNA: FiehnHILIC000674
  • MoNA: FiehnHILIC002244
  • MoNA: FiehnLib000822
  • MoNA: FiehnLib000823
  • MoNA: FiehnLibVolatile0032
  • MoNA: HMDB0006236_c_ms_954
  • MoNA: HMDB0006236_c_ms_960
  • MoNA: HMDB0006236_ms_ms_2478
  • MoNA: HMDB0006236_ms_ms_2479
  • MoNA: HMDB0006236_ms_ms_2480
  • MoNA: JP009418
  • MoNA: MoNA016780
  • Metlin: METLIN_58372
  • Coconut NaturalProduct: CNP0175320.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01377 4.1.1.43 phenylpyruvate carboxy-lyase (phenylacetaldehyde-forming)
KEGG:R02536 1.2.1.5 phenylacetaldehyde:NAD+ oxidoreductase
KEGG:R02537 1.2.1.5 aldehyde:NADP+ oxidoreductase
KEGG:R02611 1.1.1.90 phenylethylalcohol:NAD+ oxidoreductase
KEGG:R02612 1.4.9.2 phenethylamine:(acceptor) oxidoreductase (deaminating)
KEGG:R02613 1.4.3.4 phenethylamine:oxygen oxidoreductase (deaminating)
KEGG:R02615 5.3.99.7 styrene-oxide isomerase
KEGG:R10697 5.3.99.7 styrene-oxide isomerase (epoxide-cleaving)
KEGG:R11918 4.1.1.109 L-phenylalanine carboxy-lyase (oxidative-deaminating)
BioCyc:PHENDEHYD-RXN 1.2.1.39 WATER + NAD + PHENYLACETALDEHYDE --> 2 PROTON + NADH + PHENYLACETATE
BioCyc:TRANS-RXN0-284 PHENYLACETALDEHYDE --> PHENYLACETALDEHYDE
BioCyc:RXN-10817 1.4.3.21 phenylethylamine oxidase
Rhea:RHEA:14186 4.1.1.43 3-phenylpyruvate + H+ => 2-phenylacetaldehyde + CO2
Rhea:RHEA:14187 4.1.1.43 2-phenylacetaldehyde + CO2 => 3-phenylpyruvate + H+
Rhea:RHEA:14188 4.1.1.43 3-phenylpyruvate + H+ <=> 2-phenylacetaldehyde + CO2
Rhea:RHEA:21393 1.2.1.39 2-phenylacetaldehyde + NAD+ + H2O => 2-phenylacetate + NADH + 2 H+
Rhea:RHEA:21394 1.2.1.39 2-phenylacetate + NADH + 2 H+ => 2-phenylacetaldehyde + NAD+ + H2O
Rhea:RHEA:21395 1.2.1.39 2-phenylacetaldehyde + NAD+ + H2O <=> 2-phenylacetate + NADH + 2 H+
Rhea:RHEA:21605 5.3.99.7 styrene oxide => 2-phenylacetaldehyde
Rhea:RHEA:21606 5.3.99.7 2-phenylacetaldehyde => styrene oxide
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Organism Source

Taxonomy Source

  1. Actaea dahurica [ncbi taxid: 64029]
  2. Actaea heracleifolia [ncbi taxid: 64034]
  3. Actaea simplex [ncbi taxid: 64042]
  4. Akebia quinata [ncbi taxid: 13331]
  5. Akebia trifoliata [ncbi taxid: 155132]
  6. Angelica acutiloba [ncbi taxid: 55605]
  7. Angelica gigas [ncbi taxid: 85712]
  8. Angelica sinensis [ncbi taxid: 165353]
  9. Arctium lappa [ncbi taxid: 4217]
  10. Arnebia euchroma [ncbi taxid: 373122]
  11. Arnebia guttata [ncbi taxid: 419289]
  12. Artemisia argyi [ncbi taxid: 259893]
  13. Artemisia capillaris [ncbi taxid: 265783]
  14. Artemisia mongolica [ncbi taxid: 669133]
  15. Artemisia montana [ncbi taxid: 669134]
  16. Artemisia princeps [ncbi taxid: 223870]
  17. Bistorta manshuriensis [ncbi taxid: 1548133]
  18. Bistorta officinalis [ncbi taxid: 125587]
  19. Brassica hirta [ncbi taxid: ]
  20. Brassica juncea [ncbi taxid: 3707]
  21. Bupleurum chinense [ncbi taxid: 52451]
  22. Bupleurum falcatum [ncbi taxid: 46367]
  23. Bupleurum scorzonerifolium [ncbi taxid: 48105]
  24. Capsicum annuum [ncbi taxid: 4072]
  25. Carthamus tinctorius [ncbi taxid: 4222]
  26. Centaurea armena [ncbi taxid: 363414]
  27. Centaurea sessilis [ncbi taxid: ]
  28. Centranthus longiflorus ssp. longiflorus [ncbi taxid: ]
  29. Chrysanthemum indicum [ncbi taxid: 146995]
  30. Chrysanthemum x morifolium [ncbi taxid: 41568]
  31. Cimicifuga foetida [ncbi taxid: ]
  32. Cinamomum cassia [ncbi taxid: ]
  33. Cinnamomum aromaticum [ncbi taxid: 119260]
  34. Citrus limon [ncbi taxid: ]
  35. Citrus reticulata [ncbi taxid: 85571]
  36. Citrus sinensis [ncbi taxid: 2711]
  37. Citrus spp. [ncbi taxid: ]
  38. Commiphora quadricincta [ncbi taxid: 2248429]
  39. Crocus sativus [ncbi taxid: 82528]
  40. Daucus carota [ncbi taxid: 4039]
  41. Escherichia coli [ncbi taxid: 562]
  42. Eucalyptus melliodora [ncbi taxid: 183838]
  43. FOOD SAKE [ncbi taxid: ]
  44. Ganoderma lucidum [ncbi taxid: 5315]
  45. Glehnia littoralis [ncbi taxid: 48119]
  46. Gynandropsis gynandra [ncbi taxid: 190802]
  47. Hericium erinaceus [ncbi taxid: 91752]
  48. Homo sapiens [ncbi taxid: 9606]
  49. Ixora chinensis [ncbi taxid: 591727]
  50. Jatropha curcas [ncbi taxid: 180498]
  51. Lithospermum erythrorhizon [ncbi taxid: 34254]
  52. Lobelia chinensis [ncbi taxid: 368926]
  53. Lonicera confusa [ncbi taxid: 370638]
  54. Lonicera fulvotomentosa [ncbi taxid: 643838]
  55. Lonicera hypoglauca [ncbi taxid: 638626]
  56. Lonicera japonica [ncbi taxid: 105884]
  57. Lonicera macranthoides [ncbi taxid: 638627]
  58. Lycopersicon esculentum [ncbi taxid: ]
  59. Marsupella emarginata [ncbi taxid: 253513]
  60. Mentha arvensis [ncbi taxid: 292239]
  61. Mentha canadensis [ncbi taxid: 294733]
  62. Michelia alba [ncbi taxid: ]
  63. Murraya paniculata [ncbi taxid: 43711]
  64. Mus musculus [ncbi taxid: 10090]
  65. Oldenlandia diffusa [ncbi taxid: ]
  66. Perilla frutescens [ncbi taxid: 48386]
  67. Phallus impudicus [ncbi taxid: 146781]
  68. Pinellia ternata [ncbi taxid: 199225]
  69. Portulaca oleracea [ncbi taxid: 46147]
  70. Prunus armeniaca [ncbi taxid: 36596]
  71. Prunus salcina Lindl. (Blackamber,Friar) [ncbi taxid: ]
  72. Pseudomonas pseudoalcaligenes [ncbi taxid: ]
  73. Pterocarpus indicus [ncbi taxid: 100170]
  74. Saccharomyces cerevisiae [ncbi taxid: 4932]
  75. Scutellaria barbata [ncbi taxid: 396367]
  76. Sinapis alba [ncbi taxid: 3728]
  77. Solanum lycopersicum [ncbi taxid: 4081]
  78. Spongiporus leucomallellus (Murril) [ncbi taxid: ]
  79. Sraitia grosvenorii [ncbi taxid: ]
  80. Tagetes minuta [ncbi taxid: 169607]
  81. Tamarindus indica [ncbi taxid: 58860]
  82. Terminalia chebula [ncbi taxid: 155022]
  83. Vaccinium myrtillus [ncbi taxid: 180763]
  84. Vitis vinifera [ncbi taxid: 29760]
  85. Zea mays [ncbi taxid: 4577]
  86. Zingiber officinale [ncbi taxid: 94328]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-6941 styrene degradation
BioCyc:META_PWY-6071 superpathway of phenylethylamine degradation
BioCyc:META_PWY-5751 phenylethanol biosynthesis
BioCyc:ECO_2PHENDEG-PWY phenylethylamine degradation I
BioCyc:AGRO_ANAPHENOXI-PWY L-phenylalanine degradation II (anaerobic)
BioCyc:ECOL413997_2PHENDEG-PWY phenylethylamine degradation I
BioCyc:THAPS_PWY-6318 phenylalanine degradation IV (mammalian, via side chain)
BioCyc:META_2PHENDEG-PWY phenylethylamine degradation I
BioCyc:META_PWY-6534 phenylethylamine degradation II
BioCyc:META_PWY-5079 L-phenylalanine degradation III
BioCyc:ECO_BETSYN-PWY glycine betaine biosynthesis I (Gram-negative bacteria)
BioCyc:TRYPANO_ANAPHENOXI-PWY phenylalanine degradation II (anaerobic)
BioCyc:PLASMO_PWY-5079 phenylalanine degradation III
BioCyc:SCO_ANAPHENOXI-PWY L-phenylalanine degradation II (anaerobic)
BioCyc:SCO_2PHENDEG-PWY phenylethylamine degradation I
BioCyc:PCHR_PWY-5079 phenylalanine degradation III
BioCyc:ECO_PWY-6071 superpathway of phenylethylamine degradation
BioCyc:YEAST_PWY-5079 phenylalanine degradation
BioCyc:SMAN_PWY-5751 phenylethanol biosynthesis
BioCyc:ECOL316407_2PHENDEG-PWY phenylethylamine degradation I
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