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Dihydrocaffeic acid

CAT: 0804-HY-N2406-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N2406-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Dihydrocaffeic acid is a microbial metabolite of flavonoids. Dihydrocaffeic acid scavenges intracellular ROS and increases nitric oxide synthase activity. Dihydrocaffeic acid reduces phosphorylation of MAPK p38 and prevent UVB-induced skin damage. Dihydrocaffeic acid has antioxidant, anti-inflammatory and anti-cartilage degradation activities[1][2][3][4][5][6][7][8].
CAS Number
1078-61-1
Product Name Alternative
3,4-Dihydroxy-benzenepropanoic acid
UNSPSC
12352005
Hazard Statement
H315, H319, H335
Target
Endogenous Metabolite; NO Synthase; p38 MAPK; Reactive Oxygen Species (ROS)
Type
Natural Products
Related Pathways
Immunology/Inflammation; MAPK/ERK Pathway; Metabolic Enzyme/Protease; NF-κB
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/dihydrocaffeic-acid.html
Purity
99.65
Solubility
DMSO : 250 mg/mL (ultrasonic) |H2O : ≥ 100 mg/mL
Smiles
O=C(O)CCC1=CC=C(O)C(O)=C1
Molecular Formula
C9H10O4
Molecular Weight
182.17
Precautions
H315, H319, H335
References & Citations
[1]Oliveira MM, et al. Dihydrocaffeic Acid Prevents UVB-Induced Oxidative Stress Leading to the Inhibition of Apoptosis and MMP-1 Expression via p38 Signaling Pathway. Oxid Med Cell Longev. 2019 Jan 17;2019:2419096.|[2]Botta G, et al. Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses. Bioorg Med Chem. 2015 Sep 1;23 (17) :5345-51.|[3]Vázquez R, et al. Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action. Bioorg Med Chem. 2012 Sep 15;20 (18) :5537-49. |[4]Huang J, et al. Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells. J Nutr Biochem. 2004 Dec;15 (12) :722-9. |[5]Lu R, et al. Dihydrocaffeic acid improves IL-1β-induced inflammation and cartilage degradation via inhibiting NF-κB and MAPK signalling pathways. Bone Joint Res. 2023 Apr 6;12 (4) :259-273. |[6]Baeza G, et al. The colonic metabolites dihydrocaffeic acid and dihydroferulic acid are more effective inhibitors of in vitro platelet activation than their phenolic precursors. Food Funct. 2017 Mar 22;8 (3) :1333-1342.|[7]Lee K, et al. Protective Effects of Dihydrocaffeic Acid, a Coffee Component Metabolite, on a Focal Cerebral Ischemia Rat Model. Molecules. 2015 Jun 30;20 (7) :11930-40.|[8]Poquet L, et al. Effect of dihydrocaffeic acid on UV irradiation of human keratinocyte HaCaT cells. Arch Biochem Biophys. 2008 Aug 15;476 (2) :196-204.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite; Microbial Metabolite; p38 MAPK

Chemical Information

Dihydrocaffeic Acid

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.

CAS Number1078-61-1
PubChem CID348154
IUPAC Name3-(3,4-dihydroxyphenyl)propanoic acid
Molecular FormulaC9H10O4
Molecular Weight182.17
XLogP-0.5
Topological Polar Surface Area77.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Heavy Atom Count13
Formal Charge0
Complexity180
SMILES
C1=CC(=C(C=C1CCC(=O)O)O)O
InChI
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)
InChIKey
DZAUWHJDUNRCTF-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Dihydrocaffeic Acid
CAS: 1078-61-1
CID: 348154
Formula: C9H10O4
MW: 182.17
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight182.17
XLogP3-0.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass182.05790880
Monoisotopic Mass182.05790880
Topological Polar Surface Area77.8 Ų
Heavy Atom Count13
Formal Charge0
Complexity180
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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