4-Hydroxy-3,5-dimethoxycinnamic acid

4-Hydroxy-3,5-dimethoxycinnamic acid
  • CAS No.:530-59-6

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  1. This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
  2. This product is intended solely for non-clinical research, process development, quality studies, further chemical processing, or chemical synthesis. It must not be used in drug-product manufacturing, clinical trials, clinical diagnosis, or administration to humans or animals, or be sold, used as an input, submitted for regulatory filing, or released as an API or pharmaceutical material.
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4-Hydroxy-3,5-dimethoxycinnamic acid Basic information
Product Name:4-Hydroxy-3,5-dimethoxycinnamic acid
Synonyms:3,5-Dimethoxy-4-hydroxycinnamic acid, 4-Hydroxy-3,5-dimethoxycinnamic acid, Sinapic acid;3,5-Dimethoxy-4-hydroxycinnamic acid, 4-Hydroxy-3,5-dimethoxy-cinnamic acid, Sinapic acid, Sinapinic acid;3,5-Dimethoxy-4-hydroxycinnamic acid, 98%, predominantly trans isomer;3-(3,5-Dimethoxy-4-hydroxyphenyl)acrylic acid;3-(4-Hydroxy-3,5-dimethoxyphenyl)propenoic acid;3,5-Dimethoxy-4-hydroxybenzeneacrylic acid;Synapoic acid;3-(4-Hydroxy-3,5-diMethoxyphenyl)-2-propenoic Acid
CAS:530-59-6
MF:C11H12O5
MW:224.21
EINECS:208-487-3
Product Categories:Allium cepa (Onion);Allium sativum (Garlic);Armoracia rusticana (Horseradish);Berberis sp.;Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Cichorium intybus (Chicory);Linum usitatissimum (Flax);Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Aromatic Cinnamic Acids, Esters and Derivatives;Analytical Chemistry;Mass Spectrometry;Matrix Materials (MALDI-TOF-MS);Vaccinium macrocarpon (Cranberry);UltraPure MALDI Matrices;proteinmod
Mol File:530-59-6.mol
4-Hydroxy-3,5-dimethoxycinnamic acid Chemical Properties
Melting point ~202 °C
Boiling point 285.61°C (rough estimate)
density 1.1478 (rough estimate)
refractive index 1.4720 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility H2O: slightly soluble
form powder
pka4.53±0.10(Predicted)
color white
Water Solubility insoluble
BRN 2130006
Stability:Stable. Incompatible with strong oxidizing agents, strong bases. Combustible.
CAS DataBase Reference530-59-6(CAS DataBase Reference)
NIST Chemistry ReferenceCinnamic acid, 4-hydroxy-3,5-dimethoxy-(530-59-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
WGK Germany 3
Hazard Note Irritant
HS Code 29189900
MSDS Information
ProviderLanguage
3,5-Dimethoxy-4-hydroxycinnamic acid English
SigmaAldrich English
ACROS English
ALFA English
4-Hydroxy-3,5-dimethoxycinnamic acid Usage And Synthesis
Chemical Propertiesyellow-brown crystalline powder
Uses4-Hydroxy-3,5-dimethoxycinnamic acid is a commonly used matrix in MALDI mass spectrometry. It is a useful matrix for a wide variety of peptides and proteins. It serves well as a matrix for MALDI due to its ability to absorb laser radiation and to also donate protons (H+) to the analyte of interest.
UsesSinapic acid was suitable as phenolic standard for HPLC analysis in determination of Sinapic acid derivatives in Canola extracts. 10 g/L of sinapinic acid with solvent was suitable as matrix for ultraviolet laser desorption mass spectrometric determination of proteins. It was also suitable to use as matrix for MALDI-TOFMS and MALDI-ion mobility-TOFMS to determine phospholipids in tissue.
DefinitionChEBI: A monohydroxycinnamic acid that is cinnamic acid in which the phenyl hydrogens at positions 3, 4, and 5 are replaced by methoxy, hydroxy, and methoxy groups, respectively.
General DescriptionSinapic acid is an hydroxycinnamic acid derivative that occurs naturally in Brassicaceae species.
Biochem/physiol ActionsOn removal of amino group from phenylalanine, catalysing with enzyme phenylalanine ammonia-lyase forms cinnamic acid. The precursor of hydroxycinnamates is produced after hydroxylation of benzene ring. One of the precursors produced is sinapic acid. Sinapic acid exhibits antimicrobial, antioxidant, anticancer, anti-inflammatory, and anti-anxiety activity. Sinapine (sinapoyl choline) has been acknowledged as an acetylcholinesterase inhibitor, making it therapeutically applicable in treatment of various diseases. 4-Vinylsyringol (a decarboxylation product of sinapic acid) is a potent antimutagenic and antioxidative agent, involved in suppressing the induction of inflammatory cytokines and carcinogenesis. Owing to their anti-oxidative activity, these compounds have been considered to be potentially employed in the pharmaceutical industry, cosmetics and food processing.
Purification MethodsCrystallise it from water. [Beilstein 10 H 508, 10 IV 2104.]
4-Hydroxy-3,5-dimethoxycinnamic acid Preparation Products And Raw materials
Raw materialsHydrochloric acid-->Pyridine-->Piperidine-->3,4,5-Trimethoxybenzaldehyde-->Ethyl hydrogen malonate
Preparation Products2,6-DIMETHOXY-4-METHYLPHENOL

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