Syringic acid

Synonym(s):3,5-Dimethoxy-4-hydroxybenzoic acid;3,5-Dimethoxy-4-hydroxybenzoic acid, Syringic acid;4-Hydroxy-3,5-dimethoxybenzoic acid;4-Hydroxy-3,5-dimethoxy-benzoic acid;Gallic acid 3,5-dimethyl ether

CAS NO.：530-57-4
Empirical Formula: C9H10O5
Molecular Weight: 198.17
MDL number: MFCD00002552
EINECS: 208-486-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-18 14:07:02

What is Syringic acid?

Description

Syringic acid is a naturally occurring O-methylated phenolic acid that can be enzymatically degraded by some bacteria as a source of methane or methanol. It is also a component of phenolic extracts from various plants that have antioxidant and prooxidant activities. Syringic acid has been shown to inhibit aldose reductase (IC₅₀ = 213 μg/ml), proteasome activity, and cancer cell proliferation. Phenolic extracts containing syringic acid have been shown to inhibit α-amylase and α-glucosidase activities and reduce lipid peroxidation in vitro.

Chemical properties

light brown powder

The Uses of Syringic acid

antiproliferative; antifungal

The Uses of Syringic acid

Syringic Acid is used in biological studies for electron transfer from plant phenolates to carotenoid radical cations with antioxidant interaction entering the Marcus theory inverted region.

Definition

ChEBI: A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.

Natural occurence

Syringic acid can be found in several plants including Ardisia elliptica and Schumannianthus dichotomus.

Synthesis

Syringic acid can be prepared by selectively hydrolyzing (demethylating) eudesmic acid with 20% sulfuric acid.

Purification Methods

Recrystallise syringic acid from H2O using charcoal [Bogert & Coyne J Am Chem Soc 51 571 1929, Anderson & Nabenhauer J Am Chem Soc 48 3001 1926.] The methyl ester has m 107o (from MeOH), the 4-acetyl derivative has m 190o and the 4-benzoyl derivative has m 229-232o. [Hahn & Wassmuth Chem Ber 67 2050 1934, UV: Lemon J Am Chem Soc 69 2998 1947 and Pearl & Beyer J Am Chem Soc 72 1743 1950, Beilstein 10 IV 1995.]

Properties of Syringic acid

Melting point:	205-209 °C (lit.)
Boiling point:	192-193°C 14mm
Density	1.2539 (rough estimate)
refractive index	1.4570 (estimate)
Flash point:	192-193°C/14mm
storage temp.	Store below +30°C.
solubility	DMSO (Slightly), Methanol (Slightly)
pka	4.33±0.10(Predicted)
form	Powder
color	Grayish-beige to light brown
Water Solubility	5780 mg/L (25 ºC)
BRN	2115262
Stability:	Stable. Incompatible with strong bases, strong oxidizing agents.
CAS DataBase Reference	530-57-4(CAS DataBase Reference)
NIST Chemistry Reference	Benzoic acid, 4-hydroxy-3,5-dimethoxy-(530-57-4)
EPA Substance Registry System	Syringic acid (530-57-4)

Safety information for Syringic 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.