Syringaldehyde

Synonym(s):3,5-Dimethoxy-4-hydroxybenzaldehyde;4-Hydroxy-3,5-dimethoxybenzaldehyde

CAS NO.：134-96-3
Empirical Formula: C9H10O4
Molecular Weight: 182.17
MDL number: MFCD00006943
EINECS: 205-167-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-09 21:40:10

What is Syringaldehyde?

Physical properties

light yellow-green to brown crystalline powder.

Chemical properties

4-Hydroxy-3,5-dimethoxybenzaldehyde has sweet, balsamic-floral odor of considerable tenacity. lt has notes in common with Vanillin but is not as sweet and not as Vanilla-like, more floral and slightly greener.

Occurrence

Reported found in pineapple, beer, wine, grape brandy, rum, many different whisky products, sherry, roasted barley and hardwood smoke

The Uses of Syringaldehyde

Syringaldehyde is used in biological studies for the isolation and structural characterization of milled wood lignin, dioxane lignin, and cellulolytic lignin preparation from Brewer''s spent grain.

The Uses of Syringaldehyde

Syringaldehyde may be used as an analytical reference standard for the determination of the analyte in guacoextracts and pharmaceutical preparations,(1) cognacs and wines,(2) plum brandies,(4) and wheat straw(5) by various chromatography techniques.

Definition

ChEBI: A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.

Preparation

Vanillin is converted to 5-iodovanillin, which is treated with sodium methoxide to form 4-hydroxy-3,5- dimethyxybenzaldehyde.

Aroma threshold values

Aroma characteristics at 1.0%: weak sweet, slightly smoky, cinnamic, vanilla, leather-like with a phenolic medicinal nuance

Synthesis Reference(s)

Canadian Journal of Chemistry, 31, p. 476, 1953 DOI: 10.1139/v53-064
Synthetic Communications, 20, p. 2659, 1990 DOI: 10.1080/00397919008051474

General Description

Syringaldehyde is an aromatic phenolic aldehyde and a degradation product of lignin. It exhibits antioxidant activity and is reported to inhibit prostaglandin synthetase enzyme. The synthetic form of syringaldehyde is commercially used in pharmaceuticals, food, cosmetics, textiles, pulp and paper industries.

Biochem/physiol Actions

Odor at 1.0%

Purification Methods

Crystallise syringaldehyde from pet ether. [Beilstein 8 H 391, 8 IV 2718.]

Properties of Syringaldehyde

Melting point:	110-113 °C(lit.)
Boiling point:	192-193 °C14 mm Hg(lit.)
Density	1.013
refractive index	1.4500 (estimate)
FEMA	4049 \| 4-HYDROXY-3,5,-DIMETHOXY BENZALDEHYDE
Flash point:	192-193°C/14mm
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Chloroform, Methanol (Slightly)
pka	7.80±0.23(Predicted)
form	Crystalline Powder
color	Light yellow-green to brown
Odor	at 100.00 %. mild plastic woody tonka sweet
Water Solubility	very sparingly soluble
Sensitive	Air Sensitive
JECFA Number	1878
Merck	14,9015
BRN	784514
Stability:	Hygroscopic
CAS DataBase Reference	134-96-3(CAS DataBase Reference)
NIST Chemistry Reference	Benzaldehyde, 4-hydroxy-3,5-dimethoxy-(134-96-3)
EPA Substance Registry System	Syringaldehyde (134-96-3)

Safety information for Syringaldehyde

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.