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5-Hydroxyferulic acid

CAT: 0804-HY-133068-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-133068-01Size:5 mg
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Description
5-Hydroxyferulic acid is a hydroxycinnamic acid and is a metabolite of the phenylpropanoid pathway. 5-Hydroxyferulic acid is a precursor in the biosynthesis of sinapic acid and is also a COMT non-esterifed substrate[1][2][3].
CAS Number
1782-55-4
UNSPSC
12352005
Hazard Statement
H315, H319, H335
Target
COMT; Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease; Neuronal Signaling
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/5-hydroxyferulic-acid.html
Concentration
10mM
Purity
99.42
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(O)/C=C/C1=CC(OC)=C(O)C(O)=C1
Molecular Formula
C10H10O5
Molecular Weight
210.18
Precautions
H315, H319, H335
References & Citations
[1]K Parvathi, et al. Substrate Preferences of O-methyltransferases in Alfalfa Suggest New Pathways for 3-O-methylation of Monolignols. Plant J. 2001 Jan;25 (2) :193-202.|[2]S Maury, et al. Tobacco O-methyltransferases Involved in Phenylpropanoid Metabolism. The Different Caffeoyl-Coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methyltransferase and Caffeic acid/5-hydroxyferulic Acid 3/5-O-methyltransferase Classes Have Distinct Substrate Specificities and Expression Patterns. Plant Physiol. 1999 Sep;121 (1) :215-24.|[3]Inoue, et al. Substrate Preferences of Caffeic acid/5-hydroxyferulic Acid 3/5-O-methyltransferases in Developing Stems of Alfalfa (Medicago Sativa L.) . Arch Biochem Biophys. 2000 Mar 1;375 (1) :175-82.
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

Chemical Information

5-Hydroxyferulic acid

5-hydroxyferulic acid is ferulic acid in which the ring hydrogen at position 5 is substituted by a hydroxy group. It is a hydroxycinnamic acid and a methoxycinnamic acid. It is a conjugate acid of a 5-hydroxyferulate.

CAS Number1782-55-4
PubChem CID446834
IUPAC Name(E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid
Molecular FormulaC10H10O5
Molecular Weight210.18
XLogP1.1
Topological Polar Surface Area87
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count15
Formal Charge0
Complexity250
SMILES
COC1=CC(=CC(=C1O)O)/C=C/C(=O)O
InChI
InChI=1S/C10H10O5/c1-15-8-5-6(2-3-9(12)13)4-7(11)10(8)14/h2-5,11,14H,1H3,(H,12,13)/b3-2+
InChIKey
YFXWTVLDSKSYLW-NSCUHMNNSA-N
Chemical Structure
2D Structure
2D structure of 5-Hydroxyferulic acid
CAS: 1782-55-4
CID: 446834
Formula: C10H10O5
MW: 210.18
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight210.18
XLogP31.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass210.05282342
Monoisotopic Mass210.05282342
Topological Polar Surface Area87 Ų
Heavy Atom Count15
Formal Charge0
Complexity250
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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