Metabolite Card
Formula: C9H8O2 (148.0524)
SMILES: OC(=O)\C=C/C1=CC=CC=C1
Synonyms [en]
cinnamic acid; trans-cinnamic acid; Benzenepropenoic acid; Benzylideneacetic acid; Benzeneacrylic acid; E-cinnamic acid
Last reviewed on 2024-06-28.
Cite this Page
Cinnamic acid. 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: BioCAD00000008507). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Cinnamic acid, also known as (Z)-cinnamate or 3-phenyl-acrylate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Cinnamic acid can be obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Cinnamic acid exists in all living organisms, ranging from bacteria to plants to humans. Outside of the human body, cinnamic acid has been detected, but not quantified in, chinese cinnamons. In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids.
DBLinks
- CAS Registry Number: 621-82-9
- PubChem CID: 5372954
- ChEBI: 27386
- HMDB: HMDB0000567
- LipidMaps:
- KEGG: C10438
- BioCyc: CPD-674
- NCBI MeSH: cinnamic acid
- Wikipedia: Cinnamic acid
Other DBLinks
- CAS Registry Number: 102-94-3
- CAS Registry Number: 140-10-3
- CAS Registry Number: 621-82-9
- CAS Registry Number: 9045-22-1
- PubChem: 444539
- PubChem: 5372954
- PubChem: 8784
- ChEBI: ChEBI:27386
- ChEBI: ChEBI:35697
- ChEBI: ChEBI:35699
- HMDB: HMDB0000567
- HMDB: HMDB0000930
- KEGG: C00423
- KEGG: C10438
- BioCyc: CPD-674
- NCBI MeSH: cinnamic acid
- NCBI MeSH: Tinzaparin
- Wikipedia: Cinnamic acid
- Wikipedia: Cinnamic_acid
- RefMet: RM0135968
- MoNA: CCMSLIB00005463755
- MoNA: CCMSLIB00005720586
- MoNA: CCMSLIB00005720897
- MoNA: EMBL_MCF_2_0_HRMS_Library000352
- MoNA: FiehnHILIC001120
- MoNA: FiehnHILIC002643
- MoNA: HMDB0000567_ms_ms_791
- MoNA: HMDB0000567_ms_ms_792
- MoNA: HMDB0000567_ms_ms_793
- MoNA: HMDB0000930_c_ms_1245
- MoNA: HMDB0000930_ms_ms_1324
- MoNA: HMDB0000930_ms_ms_1325
- MoNA: HMDB0000930_ms_ms_1326
- MoNA: LU019151
- MoNA: LU019152
- MoNA: MoNA032560
- MoNA: MoNA032562
- MoNA: MoNA032563
- MoNA: MoNA032656
- MoNA: MoNA032657
- MoNA: MoNA032659
- MoNA: MoNA032885
- MoNA: MoNA032888
- MoNA: MoNA032891
- MoNA: MoNA033219
- MoNA: MoNA033221
- MoNA: MoNA033223
- MoNA: MoNA034688
- MoNA: MoNA034689
- MoNA: MoNA034690
- MoNA: MoNA035072
- MoNA: MoNA035074
- MoNA: MoNA035079
- MoNA: MoNA035386
- MoNA: MoNA035387
- MoNA: MoNA035395
- MoNA: MoNA037351
- MoNA: MoNA037426
- MoNA: MoNA037558
- MoNA: MoNA038105
- MoNA: MoNA038175
- MoNA: MoNA038306
- MoNA: MoNA038688
- MoNA: MoNA038817
- MoNA: PR308807
- MoNA: PR310502
- MoNA: PT101050
- MoNA: PT201050
- MoNA: RIKENPlaSMA003321
- MoNA: RIKENPlaSMA003323
- MoNA: RIKENPlaSMA003325
- MoNA: RIKENPlaSMA003328
- MoNA: RIKENPlaSMA003330
- MoNA: RIKENPlaSMA003332
- MoNA: RIKENPlaSMA003335
- MoNA: RIKENPlaSMA003337
- MoNA: RIKENPlaSMA003339
- MoNA: RIKENPlaSMA007042
- MoNA: RIKENPlaSMA007044
- MoNA: RIKENPlaSMA007046
- MoNA: RIKENPlaSMA007049
- MoNA: RIKENPlaSMA007051
- MoNA: RIKENPlaSMA007054
- MoNA: RIKENPlaSMA007056
- MoNA: RIKENPlaSMA007058
- MoNA: RP018301
- MoNA: RP018302
- MoNA: RP018303
- MoNA: RP018311
- MoNA: RP018312
- MoNA: VF-NPL-QEHF000427
- MoNA: VF-NPL-QEHF000428
- MoNA: VF-NPL-QEHF000429
- MoNA: VF-NPL-QEHF000430
- MoNA: VF-NPL-QEHF000431
- MoNA: VF-NPL-QEHF000432
- Metlin: METLIN_310
- Metlin: METLIN_63104
Class / Ontology
- WishartLab ClassyFire: [Cinnamic acids] Cinnamic acids
- RefMet: [Cinnamic acids] Cinnamic acids
- ChEBI: [CHEBI:27386] cinnamic acid
- ChEBI: [CHEBI:35697] trans-cinnamic acid
| ID | EC Number | Name |
|---|---|---|
| BioCyc:RXN-12072 | 1.14.12.19 | CPD-674 + NADH + OXYGEN-MOLECULE + PROTON --> CPD-13034 + NAD |
| BioCyc:TRANS-RXN0-466 | CPD-674 --> CPD-674 | |
| BioCyc:RXN-24042 | 1.2.98.- | CINNAMALDEHYDE + 2 CPD-10145 + WATER --> CPD-674 + 2 CPD-15487 + 3 PROTON |
| BioCyc:TRANS-CINNAMATE-4-MONOOXYGENASE-RXN | 1.14.14.91 | CPD-674 + OXYGEN-MOLECULE + Red-NADPH-Hemoprotein-Reductases --> COUMARATE + WATER + Ox-NADPH-Hemoprotein-Reductases |
| BioCyc:PHENYLALANINE-AMMONIA-LYASE-RXN | 4.3.1.25 | PHE --> CPD-674 + AMMONIUM |
| BioCyc:RXN-11269 | CPD-674 + WATER --> CPD-12218 | |
| BioCyc:RXN-9336 | CPD-674 + NAD + 2 WATER --> BENZOATE + ACET + NADH + 2 PROTON | |
| BioCyc:RXN-6721 | S-ADENOSYLMETHIONINE + CPD-674 --> CPD-6421 + ADENOSYL-HOMO-CYS | |
| BioCyc:RXN-18527 | CPD-674 + AMMONIUM --> CPD-14474 | |
| BioCyc:RXN-2001 | 6.2.1.- | CPD-674 + CO-A + ATP --> CINNAMOYL-COA + AMP + PPI |
| BioCyc:2.8.3.17-RXN | 2.8.3.17 | CINNAMOYL-COA + CPD-5921 --> CPD-674 + CPD-5922 |
| BioCyc:CINNAMATE-GLUCOSYLTRANSFERASE-RXN | 2.4.1.177 | CPD-12575 + CPD-674 --> UDP + TRANS-CINNAMOYL-BETA-D-GLUCOSE |
| BioCyc:RXN-19882 | 1.3.8.15 | CPD-674 + ETF-Reduced --> 3-PHENYLPROPIONATE + ETF-Oxidized + PROTON |
| BioCyc:TRANS-CINNAMATE-2-MONOOXYGENASE-RXN | 1.14.13.14 | PROTON + CPD-674 + OXYGEN-MOLECULE + NADPH --> WATER + NADP + 2-COUMARATE |
| BioCyc:RXN-8089 | 1.2.3.9 | CINNAMALDEHYDE + OXYGEN-MOLECULE + WATER --> PROTON + CPD-674 + HYDROGEN-PEROXIDE |
| BioCyc:RXN-803 | 4.1.1.102 | CPD-674 + PROTON --> CPD-1092 + CARBON-DIOXIDE |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| WikiPathways:WP4189 | Mevalonate arm of cholesterol biosynthesis pathway with inhibitors |