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

Molecular Formula	C9H10O5
Molecular Weight	198.1727
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23079793 \| https://www.ncbi.nlm.nih.gov/pubmed/27593755	Inhibitor 8504
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 8504	3.19 µM [Ki]
Carbonic anhydrase I 62 Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 8504	4.15 µM [Ki]
Carbonic anhydrase VA 26 Target ID: CHEMBL4789 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 8504	6.34 µM [Ki]
Carbonic anhydrase VI 17 Target ID: CHEMBL3025 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 8504	7.55 µM [Ki]
Aldose reductase 45 Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28111996	Inhibitor 8504	0.107 mM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26838182	Primary	Preclinical	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 32 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 575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23079793	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Gas chromatographic-mass spectrometric study of the degradation of phenolic compounds in wastewater olive oil by Azotobacter Chroococcum.	2008-05	17624767
Photocatalytic ozonation of phenolic wastewaters: Syringic acid, tyrosol and gallic acid.	2008-01	18161559
cis-Jasmone induces accumulation of defence compounds in wheat, Triticum aestivum.	2008-01	17681563
Photocatalytic promoted oxidation of phenolic mixtures: an insight into the operating and mechanistic aspects.	2007-12	17631936
Alkylated poly(styrene-divinylbenzene) monolithic columns for mu-HPLC and CEC separation of phenolic acids.	2007-11	17960850
Manganese affects the production of laccase in the basidiomycete Ceriporiopsis subvermispora.	2007-10	17711455
High-performance liquid chromatography as a tool for the chemical standardisation of Triphala--an Ayurvedic formulation.	2007-09-20	17879225
Degradation of 3-O-methylgallate in Sphingomonas paucimobilis SYK-6 by pathways involving protocatechuate 4,5-dioxygenase.	2007-09	17645527
Antioxidant small phenolic ingredients in Inonotus obliquus (persoon) Pilat (Chaga).	2007-08	17666849
Quantification of alkylresorcinol metabolites in urine by HPLC with coulometric electrode array detection.	2007-07	17495018
Efficiency of natural phenolic compounds regenerating alpha-tocopherol from alpha-tocopheroxyl radical.	2007-05-02	17419638
Differentiation of young red wines based on chemometrics of minor polyphenolic constituents.	2007-05-02	17407321
Phytochemical and biological studies on Saudi Commiphora opobalsamum L.	2007-05	17487607
Inhibition of gastric H+, K+-ATPase and Helicobacter pylori growth by phenolic antioxidants of Zingiber officinale.	2007-03	17295419
Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159.	2007-03	17111140
High-amylose corn exhibits better antioxidant activity than typical and waxy genotypes.	2007-01-24	17227056
High-performance liquid chromatographic method for the quantification of phenolics in 'Chyavanprash' a potent Ayurvedic drug.	2007-01-17	16971083
Antioxidant activity of sugar molasses, including protective effect against DNA oxidative damage.	2007-01	17995870
Phenolics of Moringa oleifera leaves.	2007-01	17365690
Tyrosinase from Rhizobium etli is involved in nodulation efficiency and symbiosis-associated stress resistance.	2007	17693711
Determination of some hydroxybenzoic acids and catechins in white wine samples by liquid chromatography with luminescence detection.	2006-12	17305238
Optimization of extraction of phenolic compounds from flax shives by pressurized low-polarity water.	2006-10-04	17002424
[Chemical constituents in root of Zanthoxylum nitidum].	2006-10	17225536
Effects of extraction solvent mixtures on antioxidant activity evaluation and their extraction capacity and selectivity for free phenolic compounds in barley (Hordeum vulgare L.).	2006-09-20	16968094
Insulin-sensitizing and anti-proliferative effects of Argania spinosa seed extracts.	2006-09	16951716
A new cytotoxic amide from the stem wood of Hibiscus tiliaceus.	2006-08	16732539
Plant growth inhibitors isolated from sugarcane (Saccharum officinarum) straw.	2006-07	16777531
Anti-Salmonella activity of constituents of Ardisia elliptica Thunb.	2006-06	16901814
Evaluation of the antioxidant properties and bioavailability of free and bound phenolic acids from Trichilia emetica Vahl.	2006-05-24	16427228
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.	2006-05	16677045
Phenolic acids as bioindicators of fly ash deposit revegetation.	2006-05	16418890
Conversion of sinapic acid to syringic acid by a filamentous fungus Paecilomyces variotii.	2006-04	16778358
Genotype and environmental variation in phenolic content, phenolic acid composition, and antioxidant activity of hard spring wheat.	2006-02-22	16478246
Characterization of the psychrotolerant acetogen strain SyrA5 and the emended description of the species Acetobacterium carbinolicum.	2006-01	16344912
Antimutagenic effect of phenolic acids.	2005-12	16601817
[Chemical constituents from leaves of Phyllostachys pubescens I].	2005-12	16494028
Selective extraction of derivates of p-hydroxy-benzoic acid from plant material by using a molecularly imprinted polymer.	2005-12	16405176
Effect of phenols on natural killer (NK) cell-mediated death in the K562 human leukemic cell line.	2005-11	16198604
Structure influence on biophenols solubility in model biomembranes detected by differential scanning calorimetry.	2005-10	16189796
Comparison of antioxidant activity, anthocyanins, carotenoids, and phenolics of three native fresh and sun-dried date (Phoenix dactylifera L.) varieties grown in Oman.	2005-09-21	16159191
Clostridium carboxidivorans sp. nov., a solvent-producing clostridium isolated from an agricultural settling lagoon, and reclassification of the acetogen Clostridium scatologenes strain SL1 as Clostridium drakei sp. nov.	2005-09	16166714
Methyl gallate and chemicals structurally related to methyl gallate protect human umbilical vein endothelial cells from oxidative stress.	2005-08-31	16155411
A universal HPLC method for the determination of phenolic acids in compound herbal medicines.	2005-08-24	16104776
Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L.	2005-08-10	16076123
Free phenols in maize pith and their relationship with resistance to Sesamia nonagrioides (Lepidoptera: Noctuidae) attack.	2005-08	16156590
Antioxidative phenols and phenolic glycosides from Curculigo orchioides.	2005-08	16079552
Analyses of phenolic compounds by microemulsion electrokinetic chromatography.	2005-08	16041702
Phenolic profiles of raw apricots, pumpkins, and their purees in the evaluation of apricot nectar and jam authenticity.	2005-06-15	15941324
Comparison of microemulsion electrokinetic chromatography and micellar electrokinetic chromatography methods for the analysis of phenolic compounds.	2005-06	16013824
Continuous oxidation of aromatic aldehyde to aromatic carboxylic acid by Burkholderia cepacia TM1 in a cell-holding reactor.	2001	16232987

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..

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:55:39 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:39 GMT 2025`
Record UNII	E390O181H5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SYRINGIC ACID

Official Name

English

NSC-2129

Preferred Name

English

3,5-DIMETHOXY-4-HYDROXYBENZOIC ACID

Systematic Name

English

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

Common Name

English

4-HYDROXY-3,5-DIMETHOXYBENZOIC ACID

Systematic Name

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)