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102601

Sigma-Aldrich

3,4-Dihydroxyhydrocinnamic acid

98%

Synonyme(s) :

3-(3,4-Dihydroxyphenyl)propionic acid, Hydrocaffeic acid

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About This Item

Formule linéaire :
(HO)2C6H3CH2CH2CO2H
Numéro CAS:
1078-61-1
Poids moléculaire :
182.17
Numéro Beilstein :
2213449
Numéro CE :
214-083-8
Numéro MDL:
MFCD00002776
Code UNSPSC :
12162002
ID de substance PubChem :
24846583
Nomenclature NACRES :
NA.23

Pureté

98%

Pf

136-139 °C (lit.)

Chaîne SMILES 

OC(=O)CCc1ccc(O)c(O)c1

InChI

1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)

Clé InChI

DZAUWHJDUNRCTF-UHFFFAOYSA-N

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Catégories apparentées

Description générale

3,4-Dihydroxyhydrocinnamic acid (DHCA) belongs to the class of monomers known as hydroxycinnamic acids. DHCA, also known as hydrocaffeic acid, can be polymerized to form various caffeic acid-based polymers. These polymers can be used in the development of coatings, films, and packaging materials due to their antioxidant and antimicrobial properties. caffeic acid-based polymers have also shown potential applications in drug delivery systems, tissue engineering, and encapsulation of bioactive compounds. Additionally, these polymers can be incorporated into cosmetic and personal care products due to their antioxidant and anti-inflammatory properties.

Application

3,4-Dihydroxyhydrocinnamic acid(DHCA) can be used as a monomer to prepare muscle-mimetic, bioadhesive polymers. The strong adhesive action of the polymers is due to interactions of catechol groups present at the end of the polymer terminal chain and substrate surface.
It can also be used for thesurface functionalization of nanoparticles. The functionalization with DHCA notonly improves the water solubility of nanoparticles but also provides a platformfor further modification due to the presence of surface carboxyl groups.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Reina Aoki et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(46), 16603-16610 (2011-11-18)
The ability to detect harmful chemicals rapidly is essential for the survival of all animals. In Caenorhabditis elegans (C. elegans), repellents trigger an avoidance response, causing animals to move away from repellents. Dihydrocaffeic acid (DHCA) is a water-soluble repellent and
Kebba Sabally et al.
Journal of biotechnology, 127(1), 167-176 (2006-08-15)
Lipase-catalyzed transesterification reaction of dihydrocaffeic acid (DHCA) with flaxseed oil in organic solvent media was investigated. Using equal molar concentration of DHCA and flaxseed oil, only phenolic monoacylglycerols were obtained with a transesterification yield (TY) of 18.9%. A 1:4 DHCA
Capucine Guyot et al.
Materials science & engineering. C, Materials for biological applications, 118, 111529-111529 (2020-12-02)
Fast-gelling chitosan thermosensitive hydrogels have proven to be excellent matrices for targeted drug-delivery and cell therapy. In this work, we demonstrate the possibility of designing injectable bioadhesive hydrogels with a high gelation rate by modifying chitosan with catechol (cat-CH) and
Lee E Hunt et al.
Biomolecules, 11(1) (2021-01-06)
There is ongoing interest in exploiting the antioxidant activity and other medicinal properties of natural monophenolic/polyphenolic compounds, but their generally low aqueous solubility limits their applications. Numerous studies have been undertaken to solubilize such compounds via supramolecular derivatization with co-crystal
Abhishek Jain et al.
Scientific reports, 9(1), 9191-9191 (2019-06-27)
Gut microbiome plays a vital role in human health. Human fecal and urine metabolome could provide a functional readout of gut microbial metabolism as well as its interaction with host and diet. However, this relationship still needs to be fully
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