SYRINGIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10O5
Molecular Weight	198.1727
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=CC(OC)=C1O)C(O)=O

InChI

InChIKey=JMSVCTWVEWCHDZ-UHFFFAOYSA-N

InChI=1S/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26838182 | https://www.ncbi.nlm.nih.gov/pubmed/27593755 | http://pubs.acs.org/doi/abs/10.1021/acs.cgd.6b00750

Syringic acid (SYRA) is a potential antioxidant used in traditional Chinese medicine and is an emerging nutraceutical. Current reports claim its potential anti-angiogenic, anti-glycating, anti-hyperglycaemic, neuroprotective, and memory-enhancing properties in various animal models. Syringic acid (SA) possesses anti-obesity, anti-inflammatory and anti-steatotic effects via the regulation of lipid metabolic and inflammatory genes. SA is likely to be a new natural therapeutic agent for obesity or non-alcoholic liver disease. Syringic acid reduces oxidative stress and axonal degeneration in rat sciatic nerve after ischemia/reperfusion injury. Syringic acid may play a role in the treatment of peripheral nerve injuries due to ischemia/reperfusion.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23079793 \| https://www.ncbi.nlm.nih.gov/pubmed/27593755	Inhibitor 8297
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 8297	3.19 µM [Ki]
Carbonic anhydrase I 62 Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 8297	4.15 µM [Ki]
Carbonic anhydrase VA 25 Target ID: CHEMBL4789 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 8297	6.34 µM [Ki]
Carbonic anhydrase VI 16 Target ID: CHEMBL3025 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 8297	7.55 µM [Ki]
Aldose reductase 44 Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28111996	Inhibitor 8297	0.107 mM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26838182	Primary	Preclinical	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26838182	Primary	Preclinical	Unknown Approved Use Unknown
Peripheral nerve injuries 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27593755	Primary	Preclinical	Unknown Approved Use Unknown
Spinal cord ischemia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25903968	Primary	Preclinical	Unknown Approved Use Unknown
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23079793	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Continuous oxidation of aromatic aldehyde to aromatic carboxylic acid by Burkholderia cepacia TM1 in a cell-holding reactor.	2001	16232987
[Factors of laccase producing and fermentation conditions by a new white-rot fungus AH28-2].	2001 Sep	11797226
Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection.	2002 Jun 19	12059140
Phenolic compounds profile of cornicabra virgin olive oil.	2002 Nov 6	12405780
[Two new phenylethanoid glycosides from Corallodiscus flabellata].	2003 Apr	12889125
Metabolic profiling of root exudates of Arabidopsis thaliana.	2003 Apr 23	12696935
Compounds obtained from sida acuta with the potential to induce quinone reductase and to inhibit 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in a mouse mammary organ culture model.	2003 Aug	12967190
Potential inhibitors from wet oxidation of wheat straw and their effect on ethanol production of Saccharomyces cerevisiae: wet oxidation and fermentation by yeast.	2003 Mar 20	12529889
Purification of bioethanol effluent in an UASB reactor system with simultaneous biogas formation.	2003 Oct 5	12910537
Antiproliferative and apoptotic effects of selective phenolic acids on T47D human breast cancer cells: potential mechanisms of action.	2004	14979919
Signal quenching, detoxification and mineralization of vir gene-inducing phenolics by the VirH2 protein of Agrobacterium tumefaciens.	2004 Feb	14763983
Comparison between cachaça and rum using pattern recognition methods.	2004 Jun 2	15161210
Phenyl methyl ethers: novel electron donors for respiratory growth of Desulfitobacterium hafniense and Desulfitobacterium sp. strain PCE-S.	2004 Mar	14758469
Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius.	2004 May	15165144
Low-molecular-weight components of olive oil mill waste-waters.	2004 May-Jun	15202603
Free phenols in maize pith and their relationship with resistance to Sesamia nonagrioides (Lepidoptera: Noctuidae) attack.	2005 Aug	16156590
Analyses of phenolic compounds by microemulsion electrokinetic chromatography.	2005 Aug	16041702
Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L.	2005 Aug 10	16076123
Methyl gallate and chemicals structurally related to methyl gallate protect human umbilical vein endothelial cells from oxidative stress.	2005 Aug 31	16155411
Oleanane triterpenes from Aegiceras corniculatum.	2005 Jan	15664478
Comparison of microemulsion electrokinetic chromatography and micellar electrokinetic chromatography methods for the analysis of phenolic compounds.	2005 Jun	16013824
Effect of phenols on natural killer (NK) cell-mediated death in the K562 human leukemic cell line.	2005 Nov	16198604
Genotype and environmental variation in phenolic content, phenolic acid composition, and antioxidant activity of hard spring wheat.	2006 Feb 22	16478246
Laccase-catalyzed polymerization of two phenolic compounds studied by matrix-assisted laser desorption/ionization time-of-flight and electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry with collision-induced dissociation experiments.	2006 May	16677045
Insulin-sensitizing and anti-proliferative effects of Argania spinosa seed extracts.	2006 Sep	16951716
Effects of extraction solvent mixtures on antioxidant activity evaluation and their extraction capacity and selectivity for free phenolic compounds in barley (Hordeum vulgare L.).	2006 Sep 20	16968094
Phenolics of Moringa oleifera leaves.	2007 Jan	17365690
High-amylose corn exhibits better antioxidant activity than typical and waxy genotypes.	2007 Jan 24	17227056
Inhibition of gastric H+, K+-ATPase and Helicobacter pylori growth by phenolic antioxidants of Zingiber officinale.	2007 Mar	17295419
Alkylated poly(styrene-divinylbenzene) monolithic columns for mu-HPLC and CEC separation of phenolic acids.	2007 Nov	17960850
Gas chromatographic-mass spectrometric study of the degradation of phenolic compounds in wastewater olive oil by Azotobacter Chroococcum.	2008 May	17624767

Patents

Sample Use Guides

In Vivo Use Guide

Hypertension treatment: Rats were treated with different doses of Syringic acid (SA) (25, 50, and 100 mg/kg body weight (b.w.)). The protective effect at the dose of the three tested doses (25, 50, and 100 mg/kg) of SA at a dose of 50 mg/kg b.w. exerts optimum protection.

Route of Administration: Oral

In Vitro Use Guide

The results of 3-(4,5-dimethylthiazol‑2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assays showed that pre-treatment with SA (0.1, 1, 10, and 20 uM) attenuated OGD/R-induced neuronal injury in a dose-dependent manner, with evidence of increased cell viability and decreased LDH leakage in cultured hippocampal neuronal cells..

Name

Type

Language

SYRINGIC ACID

Official Name

English

3,5-DIMETHOXY-4-HYDROXYBENZOIC ACID

Systematic Name

English

BENZOIC ACID, 4-HYDROXY-3,5-DIMETHOXY-

Common Name

English

SYRINGIC ACID [INCI]

Common Name

English

4-HYDROXY-3,5-DIMETHOXYBENZOIC ACID

Systematic Name

English

NSC-2129

Code

English

GALLIC ACID 3,5-DIMETHYL ETHER

Common Name

English

2,6-DIMETHOXY-4-CARBOXYPHENOL

Systematic Name

English

CEDAR ACID

Common Name

English

Classification Tree Code System Code

DSLD

4155 (Number of products:6)