3,4-Dihydroxybenzaldehyde (BioCAD00000003870)

blood urine plant natural products microbial natural products

Metabolite Card

Formula: C7H6O3 (138.0317)
SMILES: OC1=CC=C(C=O)C=C1O

Synonyms [en]

3,4-dihydroxybenzaldehyde; protocatechualdehyde; protocatechuic aldehyde; rancinamycin IV; 3,4-Dihydroxybenzenecarbonal; 1,2-Dihydroxy-4-formylbenzene

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

3,4-Dihydroxybenzaldehyde. 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: BioCAD00000003870). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 139-85-5
  • PubChem: 8768
  • ChEBI: ChEBI:50205
  • HMDB: HMDB0059965
  • KEGG: C16700
  • BioCyc: CPD-7616
  • NCBI MeSH: protocatechualdehyde
  • Wikipedia: Protocatechuic aldehyde
  • Wikipedia: Protocatechuic_aldehyde
  • DrugBank: DB11268
  • RefMet: RM0187313
  • MoNA: HMDB0059965_ms_ms_285672
  • MoNA: HMDB0059965_ms_ms_285673
  • MoNA: HMDB0059965_ms_ms_285674
  • MoNA: HMDB0059965_ms_ms_285675
  • MoNA: MetaboBASE0265
  • MoNA: MetaboBASE0266
  • MoNA: MetaboBASE0267
  • MoNA: MetaboBASE0268
  • MoNA: MoNA037441
  • Metlin: METLIN_63101
  • Coconut NaturalProduct: CNP0203672.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R08435 C00811<=>C16700
KEGG:R08436 C00483 + C16700<=>C21634 + C00001
Rhea:RHEA:36308 4.1.2.61 (E)-caffeoyl-CoA + H2O => 3,4-dihydroxybenzaldehyde + acetyl-CoA
Rhea:RHEA:36309 4.1.2.61 3,4-dihydroxybenzaldehyde + acetyl-CoA => (E)-caffeoyl-CoA + H2O
Rhea:RHEA:36310 4.1.2.61 (E)-caffeoyl-CoA + H2O <=> 3,4-dihydroxybenzaldehyde + acetyl-CoA
Rhea:RHEA:36312 3,4-dihydroxybenzaldehyde + NAD+ + H2O => 3,4-dihydroxybenzoate + NADH + 2 H+
Rhea:RHEA:36313 3,4-dihydroxybenzoate + NADH + 2 H+ => 3,4-dihydroxybenzaldehyde + NAD+ + H2O
Rhea:RHEA:36314 3,4-dihydroxybenzaldehyde + NAD+ + H2O <=> 3,4-dihydroxybenzoate + NADH + 2 H+
Rhea:RHEA:62429 3-hydroxy-3-(3,4-dihydroxyphenyl)propanoyl-CoA => 3,4-dihydroxybenzaldehyde + acetyl-CoA
Rhea:RHEA:62430 3,4-dihydroxybenzaldehyde + acetyl-CoA => 3-hydroxy-3-(3,4-dihydroxyphenyl)propanoyl-CoA
Rhea:RHEA:62431 3-hydroxy-3-(3,4-dihydroxyphenyl)propanoyl-CoA <=> 3,4-dihydroxybenzaldehyde + acetyl-CoA
Rhea:RHEA:63189 3,4-dihydroxybenzaldehyde + tyramine + AH2 => norbelladine + A + H2O
Rhea:RHEA:63190 norbelladine + A + H2O => 3,4-dihydroxybenzaldehyde + tyramine + AH2
Rhea:RHEA:63191 3,4-dihydroxybenzaldehyde + tyramine + AH2 <=> norbelladine + A + H2O
Rhea:RHEA:72540 3,4-dihydroxybenzaldehyde + NADP+ + H2O => 3,4-dihydroxybenzoate + NADPH + 2 H+
Rhea:RHEA:72541 3,4-dihydroxybenzoate + NADPH + 2 H+ => 3,4-dihydroxybenzaldehyde + NADP+ + H2O
Rhea:RHEA:72542 3,4-dihydroxybenzaldehyde + NADP+ + H2O <=> 3,4-dihydroxybenzoate + NADPH + 2 H+
Rhea:RHEA:73816 piceatannol + O2 => 3,5-dihydroxybenzaldehyde + 3,4-dihydroxybenzaldehyde
Rhea:RHEA:73817 3,5-dihydroxybenzaldehyde + 3,4-dihydroxybenzaldehyde => piceatannol + O2
Rhea:RHEA:73818 piceatannol + O2 <=> 3,5-dihydroxybenzaldehyde + 3,4-dihydroxybenzaldehyde
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Organism Source

Taxonomy Source

  1. Acacia adunca [ncbi taxid: 204988]
  2. Achillea biebersteinii [ncbi taxid: 282722]
  3. Aconitum leucostomum [ncbi taxid: 632164]
  4. Acrisione denticulata [ncbi taxid: 462376]
  5. Actaea racemosa [ncbi taxid: 64040]
  6. Adenia globosa [ncbi taxid: 387507]
  7. Adiantum lunulatum [ncbi taxid: ]
  8. Aglaia grandis [ncbi taxid: 306506]
  9. Alstonia spathulata [ncbi taxid: ]
  10. Amathia pinnata [ncbi taxid: ]
  11. Amorphophallus konjac [ncbi taxid: 78372]
  12. Amorphophallus konjac K.Koch [ncbi taxid: ]
  13. Anacystis montana [ncbi taxid: ]
  14. Anaphalis araneosa [ncbi taxid: ]
  15. Anarsia lineatella [ncbi taxid: 1101080]
  16. Anastatica hierochuntica [ncbi taxid: 663965]
  17. Annona cornifolia [ncbi taxid: 502529]
  18. Apollonias barbujana [ncbi taxid: ]
  19. Aquilegia ecalcarata [ncbi taxid: 46965]
  20. Archidendron ellipticum [ncbi taxid: 392766]
  21. Artemisia assoana [ncbi taxid: 1227617]
  22. Artemisia hanseniana [ncbi taxid: ]
  23. Artemisia kurramensis [ncbi taxid: 1177124]
  24. Asterospicularia laurae [ncbi taxid: 1540332]
  25. Astragalus sempervirens [ncbi taxid: 1532287]
  26. Baccharis dracunculifolia [ncbi taxid: 72900]
  27. Berberis orthobotrys [ncbi taxid: 1433323]
  28. Bhesa nitidissima [ncbi taxid: ]
  29. Bishovia boliviensis [ncbi taxid: ]
  30. Blastochloris viridis [ncbi taxid: 1079]
  31. Bletilla formosana [ncbi taxid: 466243]
  32. Blumea balsamifera [ncbi taxid: 313920]
  33. Blumea eriantha [ncbi taxid: ]
  34. Blumea mollis [ncbi taxid: 119169]
  35. Bulbinella floribunda [ncbi taxid: ]
  36. Calostephane divaricata [ncbi taxid: 1548555]
  37. Calycanthus floridus [ncbi taxid: 3429]
  38. Calycotome villosa [ncbi taxid: ]
  39. Capparis spinosa [ncbi taxid: 65558]
  40. Caragana aurantiaca [ncbi taxid: 626687]
  41. Caryocar villosum [ncbi taxid: 507520]
  42. Catunaregam tomentosa [ncbi taxid: 907773]
  43. Ceanothus velutinus [ncbi taxid: 54785]
  44. Centipeda minima [ncbi taxid: 397370]
  45. Ceriops decandra [ncbi taxid: 172013]
  46. Chaenomeles sinensis [ncbi taxid: ]
  47. Chiton tuberculatus [ncbi taxid: 1539881]
  48. Chlorophytum borivilianum [ncbi taxid: 503355]
  49. Chrysanthemum sinense [ncbi taxid: ]
  50. Cipadessa fruticosa [ncbi taxid: ]
  51. Cirsium setosum [ncbi taxid: ]
  52. Cis punctifer [ncbi taxid: ]
  53. Citrullus lanatus [ncbi taxid: 3654]
  54. Cladonia impexa [ncbi taxid: ]
  55. Cladosporium cucumerinum [ncbi taxid: 166633]
  56. Clerodendranthus spicatus [ncbi taxid: 516067]
  57. Codium dwarkense [ncbi taxid: 1676211]
  58. Colladonia triquetra [ncbi taxid: ]
  59. Colletotrichum gloeosporioides [ncbi taxid: 474922]
  60. Commiphora mukul [ncbi taxid: 2067815]
  61. Coprinopsis atramentaria [ncbi taxid: 71694]
  62. Coreopsis lanceolata [ncbi taxid: 159666]
  63. Corydalis montana [ncbi taxid: ]
  64. Cotyledon secunda [ncbi taxid: ]
  65. Cryptotympana sp. [ncbi taxid: ]
  66. Cucurbita moschata [ncbi taxid: 3662]
  67. Cymbastela coralliophila [ncbi taxid: 85786]
  68. Dalbergia ecastaphyllum [ncbi taxid: 450024]
  69. Derris amazonica [ncbi taxid: ]
  70. Diospyros cornii [ncbi taxid: ]
  71. Diplazium esculentum [ncbi taxid: 29615]
  72. Dipterocarpus dyeri [ncbi taxid: 340441]
  73. Drechslera avenae [ncbi taxid: 33199]
  74. Dumortiera hirsuta [ncbi taxid: 56917]
  75. Dytiscus marginalis [ncbi taxid: 398601]
  76. Echinopsis terscheckii [ncbi taxid: ]
  77. Episcia cupreata [ncbi taxid: 168484]
  78. Eucalyptus melliodora [ncbi taxid: 183838]
  79. Euonymus laxiflorus [ncbi taxid: 1009469]
  80. Euphorbia formosana [ncbi taxid: 458693]
  81. Forsythia suspensa [ncbi taxid: 126418]
  82. Forsythia viridissima [ncbi taxid: 205691]
  83. Fragaria vesca [ncbi taxid: 57918]
  84. Ganoderma lucidum [ncbi taxid: 5315]
  85. Garcinia scortechinii [ncbi taxid: 180116]
  86. Gardenia tubifera [ncbi taxid: 1240870]
  87. Gastrodia elata [ncbi taxid: 91201]
  88. Glechoma grandis [ncbi taxid: 672818]
  89. Glechoma longituba [ncbi taxid: 516071]
  90. Glochidion philippicum [ncbi taxid: 271531]
  91. Gnetum latifolium [ncbi taxid: 225592]
  92. Goniothalamus malayanus [ncbi taxid: 261094]
  93. Hedysarum connatum [ncbi taxid: ]
  94. Helipterum roseum [ncbi taxid: ]
  95. Himalaiella deltoidea [ncbi taxid: ]
  96. Homo sapiens [ncbi taxid: 9606]
  97. Hordeum vulgare [ncbi taxid: 4513]
  98. Hypericum laricifolium [ncbi taxid: 1136989]
  99. Ilex brevicuspis [ncbi taxid: 53199]
  100. Ilex chinensis [ncbi taxid: 1043419]
  101. Impatiens edgeworthii [ncbi taxid: 342012]
  102. Inonotus hispidus [ncbi taxid: 40469]
  103. Inonotus obliquus [ncbi taxid: 167356]
  104. Ipomoea cairica [ncbi taxid: 129201]
  105. Ipomoea digitata [ncbi taxid: ]
  106. Ipomoea purpurea [ncbi taxid: 4121]
  107. Isodon lophanthoides [ncbi taxid: 204133]
  108. Jasonia candicans [ncbi taxid: ]
  109. Kopsia grandifolia [ncbi taxid: 1750995]
  110. Lactarius sanguifluus [ncbi taxid: 111137]
  111. Lasianthus fordii [ncbi taxid: 1406743]
  112. Laurencia spectabilis [ncbi taxid: ]
  113. Leathesia nana [ncbi taxid: ]
  114. Ledebouria socialis [ncbi taxid: 34191]
  115. Lepisorus ussuriensis [ncbi taxid: 699700]
  116. Liriodendron tulipifera [ncbi taxid: 3415]
  117. Litchi chinensis [ncbi taxid: 151069]
  118. Littorina littorea [ncbi taxid: 31216]
  119. Llex chinensis [ncbi taxid: ]
  120. Lycopus europaeus [ncbi taxid: 260603]
  121. Lysimachia mauritiana [ncbi taxid: 306286]
  122. Marrubium anisodon [ncbi taxid: 2291693]
  123. Melilotus officinalis [ncbi taxid: 47083]
  124. Mentha x piperita [ncbi taxid: 34256]
  125. Myoporum platycarpum [ncbi taxid: 796003]
  126. Nasutitermes ephratae [ncbi taxid: 114633]
  127. Naucleopsis ternstroemiiflora [ncbi taxid: 241899]
  128. Ocimum gratissimum [ncbi taxid: 204144]
  129. Ongokea gore [ncbi taxid: 350425]
  130. Orobanche coerulescens [ncbi taxid: 223100]
  131. Orobanche pycnostachya [ncbi taxid: 321418]
  132. Othonna sedifolia [ncbi taxid: 405100]
  133. Palaquium canaliculatum [ncbi taxid: 3363855]
  134. Panax innovans [ncbi taxid: ]
  135. Paracoccus denitrificans [ncbi taxid: 266]
  136. Pastinaca sativa [ncbi taxid: 4041]
  137. Peltostigma guatemalense [ncbi taxid: 1136780]
  138. Pemphis acidula [ncbi taxid: 126635]
  139. Penicillium cinerascens [ncbi taxid: 70096]
  140. Perilla frutescens [ncbi taxid: 48386]
  141. Persea mexicana [ncbi taxid: ]
  142. Persicaria perfoliata [ncbi taxid: 371028]
  143. Pharbitis nil [ncbi taxid: ]
  144. Phellinus igniarius [ncbi taxid: 40472]
  145. Phlojodicarpus sibiricus [ncbi taxid: 2893997]
  146. Phlomoides rotata [ncbi taxid: 572115]
  147. Phoebe pittieri [ncbi taxid: ]
  148. Physalis sordida [ncbi taxid: 304128]
  149. Picea jezoensis var. jezoensis [ncbi taxid: 689841]
  150. Pinellia ternata [ncbi taxid: 199225]
  151. Pithecellobium racemosum [ncbi taxid: ]
  152. Pleocarphus revolutus [ncbi taxid: 1910961]
  153. Polyporus umbellatus [ncbi taxid: 158314]
  154. Polysiphonia lanosa [ncbi taxid: ]
  155. Posidonia oceanica [ncbi taxid: 55489]
  156. Premna odorata [ncbi taxid: 1037421]
  157. Pseudoalteromonas luteoviolacea [ncbi taxid: 43657]
  158. Psoralea corylifolia [ncbi taxid: ]
  159. Pterocarpus officinalis [ncbi taxid: 330896]
  160. Pyrus calleryana [ncbi taxid: 36597]
  161. Ranunculus sceleratus [ncbi taxid: 147635]
  162. Ranzania japonica [ncbi taxid: 63353]
  163. Rauvolfia vomitoria [ncbi taxid: 403115]
  164. Rhabdonia verticillata [ncbi taxid: 257557]
  165. Rhizoctonia repens [ncbi taxid: ]
  166. Rhodobacter sphaeroides [ncbi taxid: ]
  167. Rothmannia wittii [ncbi taxid: ]
  168. Rumex chalepensis [ncbi taxid: 1786032]
  169. Rumex japonicus [ncbi taxid: 174651]
  170. Rumex maritimus [ncbi taxid: 467604]
  171. Sabina sargentii [ncbi taxid: ]
  172. Salvia miltiorrhiza [ncbi taxid: 226208]
  173. Salvia miltiorrihiza [ncbi taxid: ]
  174. Salvia prionitis [ncbi taxid: 588964]
  175. Salvia przewalskll [ncbi taxid: ]
  176. Salvia syriaca [ncbi taxid: 1685717]
  177. Salvia trijuga [ncbi taxid: 342065]
  178. Sanicula epipactis [ncbi taxid: 52473]
  179. Sarcophyton buitendijki [ncbi taxid: 358794]
  180. Sarothamnus patens [ncbi taxid: ]
  181. Scopolia atropoides [ncbi taxid: ]
  182. Scutellaria amoena [ncbi taxid: 1052904]
  183. Senecio heliopsis [ncbi taxid: ]
  184. Sinularia depressa [ncbi taxid: ]
  185. Solanum laxum [ncbi taxid: 205558]
  186. Solidago petiolaris [ncbi taxid: 72976]
  187. Sordaria araneosa [ncbi taxid: 573841]
  188. Streptomyces avermectinius [ncbi taxid: ]
  189. Streptomyces lincolnensis [ncbi taxid: 1915]
  190. Streptomyces purpurogeneiscleroticus [ncbi taxid: 68259]
  191. Streptomyces roseoverticillatus [ncbi taxid: 66429]
  192. Swertia franchetiana [ncbi taxid: 50785]
  193. Synadenium pereskiifolium [ncbi taxid: ]
  194. Tabernaemontana divaricata [ncbi taxid: 52861]
  195. Tanacetum parthenium [ncbi taxid: 127999]
  196. Taonia australasica [ncbi taxid: ]
  197. Taraxacum borealisinense [ncbi taxid: ]
  198. Taraxacum coreanum [ncbi taxid: 1041103]
  199. Taraxacum mongolicum [ncbi taxid: 90037]
  200. Taraxacum officinale [ncbi taxid: 50225]
  201. Taraxacum platycarpum [ncbi taxid: 170727]
  202. Taxus drupacea [ncbi taxid: ]
  203. Tetrapanax papyrifer [ncbi taxid: 46417]
  204. Tolypothrix tenuis [ncbi taxid: 457083]
  205. Trachycarpus fortunei [ncbi taxid: 14027]
  206. Vaccinium oxycoccos [ncbi taxid: 516948]
  207. Vernonia lanuginosa [ncbi taxid: ]
  208. Viguiera incana [ncbi taxid: 1048928]
  209. Vitex negundo [ncbi taxid: 361442]
  210. Vitis vinifera [ncbi taxid: 29760]
  211. Vittaria anguste-elongata [ncbi taxid: ]
  212. Wikstroemia retusa [ncbi taxid: 1872696]
  213. Xanthium sibiricum [ncbi taxid: 576365]
  214. Xanthium strumarium [ncbi taxid: 318068]
  215. Zaluzania grayana [ncbi taxid: 191180]
  216. Zanthoxylum acutifolium [ncbi taxid: ]
  217. Zanthoxylum myriacanthum [ncbi taxid: 1009510]
  218. Zanthoxylum tetraspermum [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-7826 Amaryllidacea alkaloids biosynthesis
BioCyc:META_PWY-6667 resveratrol degradation
BioCyc:META_PWY-8003 trans-caffeate degradation (aerobic)
BioCyc:META_PWY-5665 vanillin biosynthesis I
PlantCyc:PLANT_PWY-5665 vanillin biosynthesis I
PlantCyc:PLANT_PWY-7826 Amaryllidacea alkaloids biosynthesis
PlantCyc:VANILLA_PWY-5665 vanillin biosynthesis I
View All Pathways