Syringic acid

Names

[ CAS No. ]:
530-57-4

[ Name ]:
Syringic acid

[Synonym ]:
QVR DQ CO1 EO1
Gallic acid 3,5-dimethyl ether
Cedar acid
3,5-Dimethoxy-4-hydroxybenzoic acid
4-hydroxy-3,5-O-dimethylbenzoic acid
Benzoic acid, 4-hydroxy-3,5-dimethoxy-
4-Hydroxy-3,5-dimethoxybenzoic acid
Syringic acid
3,5-Dimethoxy-4-hydroxybenzoic acid 4-Hydroxy-3,5-dimethoxy-benzoic acid
Benzoic acid,4-hydroxy-3,5-dimethoxy
4-Hydroxy-3,5-dimethoxy-benzoic acid
3,5-Dimethoxy-4-hydroxybenzyl acid
EINECS 208-486-8
3,5-Dimethoxy-4-hydroxybenzoate
MFCD00002552

Biological Activity

[Description]:

Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation.

[Related Catalog]:

Research Areas >> Metabolic Disease

Natural Products >> Phenols

[Target]

Human Endogenous Metabolite

[In Vitro]

Syringic acid is a phenol present in some distilled alcohol beverages. It is also a product of microbial (gut) metabolism of anthocyanins and other polyphenols that have been consumed[1]. Research suggests that phenolics from wine may play a positive role against oxidation of low-density lipoprotein (LDL), which is a key step in the development of atherosclerosis. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation[2].

[References]

[1]. Forester SC, et al. Identification of Cabernet Sauvignon anthocyanin gut microflora metabolites. J Agric Food Chem. 2008 Oct 8;56(19):9299-304.

[2]. Kalkan Yildirim H, et al. Protection capacity against low-density lipoprotein oxidation and antioxidant potential of some organic and non-organic wines. Int J Food Sci Nutr. 2004 Aug;55(5):351-62.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
379.5±42.0 °C at 760 mmHg

[ Melting Point ]:
205-209 °C(lit.)

[ Molecular Formula ]:
C₉H₁₀O₅

[ Molecular Weight ]:
198.173

[ Flash Point ]:
155.0±21.4 °C

[ Exact Mass ]:
198.052826

[ PSA ]:
75.99000

[ LogP ]:
1.13

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.566

[ Stability ]:
Stable. Incompatible with strong bases, strong oxidizing agents.

[ Water Solubility ]:
5780 mg/L (25 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DH2090000

CHEMICAL NAME :: Benzoic acid, 4-hydroxy-3,5-dimethoxy-

CAS REGISTRY NUMBER :: 530-57-4

BEILSTEIN REFERENCE NO. :: 2115262

LAST UPDATED :: 199709

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C9-H10-O5

MOLECULAR WEIGHT :: 198.19

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 3 gm/L

REFERENCE :: CALEDQ Cancer Letters (Shannon, Ireland). (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1975- Volume(issue)/page/year: 14,251,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DH2090000

[ HS Code ]:
29189090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Development of antibodies for determination of alkylresorcinol metabolites in human urine and elucidation of ELISA cross-reactivity.

J. Immunol. Methods 413 , 12-24, (2014)

Alkylresorcinols (ARs) are amphiphilic phenolic lipids and their two main metabolites, 3-(3,5-dihydroxyphenyl)-propanoic acid (DHPPA) and 3,5-dihydroxybenzoic acid (DHBA), can be used as biomarkers of...

Effect of selected Saccharomyces cerevisiae yeast strains and different aging techniques on the polysaccharide and polyphenolic composition and sensorial characteristics of Cabernet Sauvignon red wines.

J. Sci. Food Agric. 95 , 2132-44, (2015)

The objective of this work was to study the effect of two Saccharomyces cerevisiae yeast strains with different capabilities of polysaccharide liberation during alcoholic fermentation in addition to s...

Comparison between ATR-IR, Raman, concatenated ATR-IR and Raman spectroscopy for the determination of total antioxidant capacity and total phenolic content of Chinese rice wine.

Food Chem. 194 , 671-9, (2015)

The application of attenuated total reflectance infrared spectroscopy (ATR-IR), Raman spectroscopy (RS) and combination of ATR-IR and RS for measurements of total antioxidant capacity (TAC) and total ...