4-Hydroxycinnamic acid (p-Coumaric acid)
Compound Structure: |
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Synonyms: | p-coumaric acid;4-Hydroxycinnamic acid;501-98-4;p-Hydroxycinnamic acid;trans-4-Hydroxycinnamic acid;4-Coumaric acid;7400-08-0;trans-p-Coumaric acid;p-Cumaric acid;3-(4-hydroxyphenyl)acrylic acid;p-Hydroxy-cinnamic acid | ||||||||||||||||||||||||||||||||||||||||||
Compound ID: | NMPC-419 | ||||||||||||||||||||||||||||||||||||||||||
PubChem ID: | |||||||||||||||||||||||||||||||||||||||||||
Molecular Formula: | C9H8O3 | ||||||||||||||||||||||||||||||||||||||||||
Canonical SMILES: | C1=CC(=CC=C1C=CC(=O)O)O | ||||||||||||||||||||||||||||||||||||||||||
InChIKey: | NGSWKAQJJWESNS-ZZXKWVIFSA-N | ||||||||||||||||||||||||||||||||||||||||||
About the compound: | 4-Coumaric acid belongs to the hydroxycinnamic acids category, a crucial phenolic compound found across various plant species, playing a key role in creating lignols which are essential for plant structure. It's detected in numerous foods including peanuts, navy beans, tomatoes, carrots, basil, garlic, as well as barley, wine, vinegar, and honey. This compound is produced from cinnamic acid through the activity of a P450-dependent enzyme known as 4-cinnamic acid hydroxylase or from L-tyrosine by tyrosine ammonia lyase. Notably, p-coumaric acid is a precursor to various natural products, such as 4-ethylphenol, highlighting its importance in the food and beverage sector[1]. Recognized for its potential health benefits, 4-coumaric acid is researched for its antioxidant, antimicrobial, anti-melanogenic, and anticancer qualities, pointing towards its promising use in health and medical fields and emphasizing the necessity for further investigation into its action mechanisms and effectiveness[2]. As an organic compound, particularly within the phenylpropanoids and polyketides class, it directly stems from hydroxycinnamic acids and encompasses several forms like coumaric and cinnamic acids. The molecular structure and behavior of 4-coumaric acid demonstrate its capacity for varied biological activities and applications across different domains, including the creation of eco-friendly biochemicals[3]. Reference 1. Wikipedia contributors. "p-Coumaric acid." Wikipedia, The Free Encyclopedia. https://en.wikipedia.org/wiki/P-Coumaric_acid. 2. Kaur, J., & Kaur, R. (2022). p-Coumaric acid: a naturally occurring chemical with potential therapeutic applications. Current Organic Chemistry, 26(14), 1333-1349. https://benthamscience.com/article/126952 3. DrugBank. "p-Coumaric acid: Uses, Interactions, Mechanism of Action." DrugBank Online. Last modified date not provided. https://go.drugbank.com/drugs/DB04066. GHS Hazard Statements • H301+H311 (63.64%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal] • H301 (68.18%): Toxic if swallowed [Danger Acute toxicity, oral] • H311 (68.18%): Toxic in contact with skin [Danger Acute toxicity, dermal] • H314 (68.18%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation] • H315 (31.82%): Causes skin irritation [Warning Skin corrosion/irritation] • H317 (68.18%): May cause an allergic skin reaction [Warning Sensitization, Skin] • H318 (63.64%): Causes serious eye damage [Danger Serious eye damage/eye irritation] • H319 (31.82%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] • H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
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Properties: |
Chemical
and Physical Properties
Source: PubChem |
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Source Species: |
Saccharum officinarum |