Basic information
- CAS
1078-61-1- Standard SMILES
O=C(O)CCc1ccc(O)c(O)c1- InChIKey
DZAUWHJDUNRCTF-UHFFFAOYSA-N- Molecular formula
- C9H10O4
- Average molar mass
- 182.17 g/mol
- Monoisotopic mass
- 182.0579088
Overview
3-(3,4-dihydroxyphenyl)propanoic acid is a monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity. It has a role as an antioxidant and a human xenobiotic metabolite. It is functionally related to a 3-phenylpropionic acid. It is a conjugate acid of a 3-(3,4-dihydroxyphenyl)propanoate.
Names & identifiers
- Preferred name
- Dihydrocaffeic Acid
- IUPAC
- 3-(3,4-dihydroxyphenyl)propanoic acid
- English name
- Dihydrocaffeic acid
- Molecular formula
- C9H10O4
- Molecular weight
- 182.17
Names & synonyms
Dihydrocaffeic acid1078-61-13,4-Dihydroxyphenylpropionic acidBenzenepropanoic acid, 3,4-dihydroxy-3,4-Dihydroxybenzenepropanoic acidHydrocinnamic acid, 3,4-dihydroxy-MSW0228VUBDTXSID40221919RefChem:486243DTXCID201444103-(3,4-Dihydroxyphenyl)propionic acid3-(3,4-Dihydroxyphenyl)propanoic acid
Show more names
NSC 407275NSC 6240073-propionic acidDIHYDROCAFFEIC ACID(RG)
3,4-Dihydroxyhydrocinnamic acidHydrocaffeic acid3,4-Dihydroxy-benzenepropanoic acid3,4-Dihydroxybenzenepropionic acidHYKOPMFCD00002776Hydrocaffeate3,4-Dihydroxydihydrocinnamic acid
Database identifiers
- CAS
1078-61-1、71693-95-3- PubChem CID
- 348154
- DTXSID
DTXSID40221919- ChEMBL
CHEMBL136927- ChEBI
CHEBI:48400
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 180
Experimental & physicochemical properties
Solubility428 mg/mL
Melting Point136 °C
Physical DescriptionSolid
Collision Cross Section133.05 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 136 · 136-139 °C(lit.)
- Boiling point
- 418 ℃ · 418℃
- Density
- 1.398 · 1.398
- Flash point
- 220 ℃ · 220℃
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 4.75 · 4.75±0.10(Predicted)
- color
- Pale Beige to Pale Brown
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- MW5143500
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Metabolism/Metabolites3,4-dihydroxyphenylpropionic acid has known human metabolites that include 4-hydroxy- 4-Hydroxyphenylpropionic acid and 3-(3-hydroxyphenyl)propanoic acid.
Cellular LocationsCytoplasm
Applications
DescriptionDihydrocaffeic acid is a polyphenol that has diverse biological activities, including antioxidant, neuroprotective, and enzyme inhibitory properties. Dihydrocaffeic acid scavenges ABTS (; IC50 = 81.86 μg/ml) and 2,2-diphenyl-1-picrylhydrazyl (DPPH; ; IC50 = 192.86 μg/ml) radicals and increases the survival of RGC-5 mouse retinal ganglion cells under hypoxic conditions and in the presence of S-nitroso-N-acetyl-D,L-penicillamine (SNAP; ) in a concentration-dependent manner. It also decreases endothelial nitric oxide synthase (eNOS) activity in EA.hy926 human endothelial cells in a concentration-dependent manner. In vivo, dihydrocaffeic acid (30 mg/kg) decreases infarct size in a rat model of transient ischemia induced by middle cerebral artery occlusion (MCAO).
Uses3-(3,4-Dihydroxyphenyl)propionic acid it can be used to produce 3-(3,4-dihydroxy-phenyl)-propionic acid octyl ester by heating.
UsesDihydrocaffeic Acid is a natural product containing a catechol group with an α,β-unsaturated carboxylic acid chain. Dihydrocaffeic Acid has been shown to have hepatoprotective activity. Dihydrocaffei c Acid is a metabolite of Caffeic Acid (C08000) with potent antioxidant properties.
Upstream & downstream products
Upstream raw materials
Related reactions
8 records
Compound notes
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