4-Hydroxy-3,5-dimethoxycinnamic acid

Synonym(s):3,5-Dimethoxy-4-hydroxycinnamic acid;4-Hydroxy-3,5-dimethoxy-cinnamic acid;Sinapinic acid

CAS NO.：530-59-6
Empirical Formula: C11H12O5
Molecular Weight: 224.21
MDL number: MFCD00004401
EINECS: 208-487-3
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-28 18:16:09

4-Hydroxy-3,5-dimethoxycinnamic acid Structural

What is 4-Hydroxy-3,5-dimethoxycinnamic acid?

Chemical properties

yellow-brown crystalline powder

The Uses of 4-Hydroxy-3,5-dimethoxycinnamic acid

4-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.

The Uses of 4-Hydroxy-3,5-dimethoxycinnamic acid

Sinapic 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.

Definition

ChEBI: 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 Description

Sinapic acid is an hydroxycinnamic acid derivative that occurs naturally in Brassicaceae species.

Biochem/physiol Actions

On 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 Methods

Crystallise it from water. [Beilstein 10 H 508, 10 IV 2104.]

Properties of 4-Hydroxy-3,5-dimethoxycinnamic acid

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
pka	4.53±0.10(Predicted)
color	white
Odor	at 100.00?%. odorless
Water Solubility	insoluble
BRN	2130006
Stability:	Stable. Incompatible with strong oxidizing agents, strong bases. Combustible.
CAS DataBase Reference	530-59-6(CAS DataBase Reference)
NIST Chemistry Reference	Cinnamic acid, 4-hydroxy-3,5-dimethoxy-(530-59-6)

Safety information for 4-Hydroxy-3,5-dimethoxycinnamic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.