4-Hydroxycinnamyl aldehyde (BioCAD00000004380)

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Metabolite Card

Formula: C9H8O2 (148.0524)
SMILES: OC1=CC=C(\C=C\C=O)C=C1

Synonyms [en]

p-coumaraldehyde; 4-Hydroxycinnamyl aldehyde; trans-p-Hydroxycinnamaldehyde; (E)-3-(4-Hydroxyphenyl)-2-propenal; (2E)-3-(4-hydroxyphenyl)prop-2-enal; trans-4-hydroxycinnamaldehyde

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

4-Hydroxycinnamyl aldehyde. 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: BioCAD00000004380). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

p-Coumaraldehyde (CAS: 2538-87-6), also known as 4-hydroxycinnamaldehyde or 3-(4-hydroxyphenyl)-2-propenal, belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. p-Coumaraldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, p-coumaraldehyde has been detected, but not quantified in, several different foods, such as red rice, lindens, peaches, white lupines, and evergreen huckleberries. This could make p-coumaraldehyde a potential biomarker for the consumption of these foods. p-Coumaraldehyde is also a constituent of Alpinia galanga (greater galangal) rhizomes and Cucurbita maxima.

Cytoplasm Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 20711-53-9
  • CAS Registry Number: 2538-87-6
  • CAS Registry Number: 82140-91-8
  • PubChem: 440733
  • PubChem: 641301
  • PubChem: 71407359
  • ChEBI: ChEBI:181650
  • ChEBI: ChEBI:28353
  • HMDB: HMDB0040986
  • HMDB: HMDB0135648
  • HMDB: HMDB40986
  • KEGG: C05608
  • BioCyc: COUMARALDEHYDE
  • NCBI MeSH: p-hydroxycinnamaldehyde
  • RefMet: RM0030563
  • MoNA: PR309443
  • MoNA: PR310503
  • MoNA: RIKENPlaSMA004040
  • MoNA: RIKENPlaSMA004041
  • MoNA: RIKENPlaSMA004043
  • MoNA: RIKENPlaSMA004045
  • MoNA: RIKENPlaSMA004047
  • MoNA: RIKENPlaSMA004049
  • MoNA: RIKENPlaSMA004051
  • MoNA: RIKENPlaSMA004053
  • MoNA: RIKENPlaSMA004055
  • MoNA: RIKENPlaSMA004057
  • MoNA: RIKENPlaSMA004059
  • MoNA: RIKENPlaSMA004061
  • MoNA: RIKENPlaSMA008081
  • MoNA: RIKENPlaSMA008083
  • MoNA: RIKENPlaSMA008085
  • MoNA: RIKENPlaSMA008087
  • MoNA: RIKENPlaSMA008088
  • MoNA: RIKENPlaSMA008090
  • MoNA: RIKENPlaSMA008092
  • MoNA: RIKENPlaSMA008094
  • MoNA: RIKENPlaSMA008095
  • MoNA: RIKENPlaSMA008097
  • MoNA: RIKENPlaSMA008099
  • Metlin: METLIN_44643
  • Coconut NaturalProduct: CNP0344624.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01615 1.2.1.44 4-hydroxycinnamyl aldehyde:NADP+ oxidoreductase (CoA-hydroxycinnamoylating)
KEGG:R06579 1.14.13.- C05608<=>C10945
KEGG:R07437 1.1.1.195 4-coumaryl alcohol:NADP+ oxidoreductase
Rhea:RHEA:45725 1.1.1.195 (E)-4-coumaroyl alcohol + NADP+ => (E)-4-coumaraldehyde + NADPH + H+
Rhea:RHEA:45726 1.1.1.195 (E)-4-coumaraldehyde + NADPH + H+ => (E)-4-coumaroyl alcohol + NADP+
Rhea:RHEA:45727 1.1.1.195 (E)-4-coumaroyl alcohol + NADP+ <=> (E)-4-coumaraldehyde + NADPH + H+
Rhea:RHEA:64653 1.2.1.44 (E)-4-coumaraldehyde + NADP+ + CoA => (E)-4-coumaroyl-CoA + NADPH + H+
Rhea:RHEA:64654 1.2.1.44 (E)-4-coumaroyl-CoA + NADPH + H+ => (E)-4-coumaraldehyde + NADP+ + CoA
Rhea:RHEA:64655 1.2.1.44 (E)-4-coumaraldehyde + NADP+ + CoA <=> (E)-4-coumaroyl-CoA + NADPH + H+
Rhea:RHEA:76452 (E)-4-coumaroyl alcohol + A => (E)-4-coumaraldehyde + AH2
Rhea:RHEA:76453 (E)-4-coumaraldehyde + AH2 => (E)-4-coumaroyl alcohol + A
Rhea:RHEA:76454 (E)-4-coumaroyl alcohol + A <=> (E)-4-coumaraldehyde + AH2
Rhea:RHEA:82264 (E)-4-coumaraldehyde + reduced [NADPH—hemoprotein reductase] + O2 => (E)-caffeyl aldehyde + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:82265 (E)-caffeyl aldehyde + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => (E)-4-coumaraldehyde + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:82266 (E)-4-coumaraldehyde + reduced [NADPH—hemoprotein reductase] + O2 <=> (E)-caffeyl aldehyde + oxidized [NADPH—hemoprotein reductase] + H2O + H+
BioCyc:RXN-16806 1.14.14.- COUMARALDEHYDE + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> CPD-18120 + Ox-NADPH-Hemoprotein-Reductases + WATER
BioCyc:RXN-1102 1.1.1.195 COUMARALDEHYDE + NADPH + PROTON --> COUMARYL-ALCOHOL + NADP
BioCyc:RXN-1101 1.2.1.44 P-COUMAROYL-COA + NADPH + PROTON --> COUMARALDEHYDE + CO-A + NADP
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Organism Source

Taxonomy Source

  1. Ajania fruticulosa [ncbi taxid: 99024]
  2. Alpinia galanga [ncbi taxid: 94327]
  3. Annona glabra [ncbi taxid: 301703]
  4. Astragalus curvicarpus [ncbi taxid: 90171]
  5. Carya cathayensis [ncbi taxid: 139927]
  6. Chamaecyparis formosensis [ncbi taxid: 187461]
  7. Citrullus lanatus [ncbi taxid: 3654]
  8. Colchicum autmnale [ncbi taxid: ]
  9. Colchicum hierosolymitanum [ncbi taxid: ]
  10. Colchicum tunicatum [ncbi taxid: 1094127]
  11. Eucalyptus radiata [ncbi taxid: 87679]
  12. Fructus galangae [ncbi taxid: ]
  13. Gloriosa superba [ncbi taxid: 41220]
  14. Ilex taubertiana [ncbi taxid: 224368]
  15. Pandanus tectorius [ncbi taxid: 4726]
  16. Sonchus oleraceus [ncbi taxid: 50207]
  17. Spiraea formosana [ncbi taxid: 409510]
  18. Torreya grandis [ncbi taxid: 58047]
  19. Torreya nuncifera [ncbi taxid: ]
  20. Urceolaria bryophila [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:ARA_PWY-361 phenylpropanoid biosynthesis
BioCyc:META_PWY-361 phenylpropanoid biosynthesis
BioCyc:META_PWY-7682 arabidopyrone biosynthesis
PlantCyc:SVIRIDIS_PWY-361 monolignol biosynthesis
PlantCyc:AHYPOCHONDRIACUS_PWY-361 monolignol biosynthesis
PlantCyc:ASPARAGUS_PWY-361 monolignol biosynthesis
PlantCyc:WHEATA_PWY-361 monolignol biosynthesis
PlantCyc:BANANA_PWY-361 monolignol biosynthesis
PlantCyc:BARLEY_PWY-361 monolignol biosynthesis
PlantCyc:BREADWHEAT_PWY-361 monolignol biosynthesis
PlantCyc:CARNATION_PWY-361 monolignol biosynthesis
PlantCyc:CASSAVA_PWY-361 monolignol biosynthesis
PlantCyc:CCAPSULARIS_PWY-361 monolignol biosynthesis
PlantCyc:RUBBERTREE_PWY-361 monolignol biosynthesis
PlantCyc:COCOA_PWY-361 monolignol biosynthesis
PlantCyc:COMMONBEAN_PWY-361 monolignol biosynthesis
PlantCyc:CROSEUS_PWY-361 monolignol biosynthesis
PlantCyc:OMERIDIONALIS_PWY-361 monolignol biosynthesis
PlantCyc:ONIVARA_PWY-361 monolignol biosynthesis
PlantCyc:CORKOAK_PWY-361 monolignol biosynthesis
View All Pathways