ChemFOnt: Showing chemical card for Syringic acid (CFc000001398)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:01 UTC

Chemfont ID

CFc000001398

Molecule Identification

Common Name

Syringic acid

Definition

Syringic acid, also known as syringate or cedar acid, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Outside of the human body, Syringic acid is found, on average, in the highest concentration within a few different foods, such as common walnuts, swiss chards, and olives and in a lower concentration in apples, tarragons, and peanuts. Syringic acid has also been detected, but not quantified in several different foods, such as sweet marjorams, silver lindens, bulgurs, annual wild rices, and barley. This could make syringic acid a potential biomarker for the consumption of these foods. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. 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 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 (in fruits and alcoholic beverages - PMID:18767860 ). Syringic acid is also a microbial metabolite that can be found in Bifidobacterium (PMID:24958563 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cedar acid	ChEBI
Gallic acid 3,5-dimethyl ether	ChEBI
Syringate	Kegg
4-Hydroxy-3,5-dimethoxybenzoate	Kegg
Gallate 3,5-dimethyl ether	Generator
4-Hydroxy-3,5-dimethoxybenzoic acid	Generator
Syringic acid cu (+2) salt (1:1)	MeSH
3,5-Dimethoxy-4-hydroxybenzoate	HMDB
3,5-Dimethoxy-4-hydroxybenzoic acid	HMDB
3,5-Dimethoxybenzoyl hydrazine	HMDB
3,5-Dimethyl-4-hydroxybenzoate	HMDB
3,5-Dimethyl-4-hydroxybenzoic acid	HMDB
4-Hydroxy-3,5-dimethylbenzoate	HMDB
4-Hydroxy-3,5-dimethylbenzoic acid	HMDB
Syringlicacid	HMDB
Syringic acid	HMDB
3,5-dimethoxygallic acid	HMDB
3,5-O-dimethylgallic acid	HMDB

Chemical Formula

C₉H₁₀O₅

Average Molecular Weight

198.174

Monoisotopic Molecular Weight

198.052823422

IUPAC Name

4-hydroxy-3,5-dimethoxybenzoic acid

Traditional Name

syringic acid

CAS Registry Number

530-57-4

SMILES

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

InChI Identifier

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)

InChI Key

JMSVCTWVEWCHDZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Phenol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:68329 )
dimethoxybenzene (CHEBI:68329 )
benzoic acids (CHEBI:68329 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16019270)
Saliva (HMDB: HMDB0002085)

Excreta

Biofluid or Excreta

Urine (PMID: 12771321)
Feces (PMID: 24010549)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002085)

Source

Exogenous

Exogenous (HMDB: HMDB0002085)

Food

Food (HMDB: HMDB0002085)
Legumes (HMDB: HMDB0002085)

Beverage

Fermented beverage

Distilled beverage

Spirit (FooDB: FOOD00276)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Whisky (FooDB: FOOD00623)

Alcoholic beverage

Red wine (HMDB: HMDB0002085)

Fortified wines

Sherry (FooDB: FOOD00632)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Berry

Tropical fruit

Coconut (FooDB: FOOD00336)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Fruits (HMDB: HMDB0002085)

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Olive (FooDB: FOOD00121)
Garden tomato (FooDB: FOOD00171)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)

Root vegetable

Cabbage

Broccoli (FooDB: FOOD00034)
Cauliflower (FooDB: FOOD00031)

Leaf vegetable

Swiss chard (FooDB: FOOD00237)
Romaine lettuce (FooDB: FOOD00888)

Vegetables (HMDB: HMDB0002085)

Tuber

Arrowroot (FooDB: FOOD00290)

Cereal and cereal product

Cereal

Cereal product

Breakfast cereal (FooDB: FOOD00270)
Whole grain cereal products (HMDB: HMDB0002085)
Flour (FooDB: FOOD00799)
Bulgur (FooDB: FOOD00741)

Leavened bread

Rye bread (FooDB: FOOD00809)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Pea

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Cocoa and cocoa product

Cocoa product

Cocoa powder (FooDB: FOOD00685)

Cocoa and cocoa products (HMDB: HMDB0002085)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0002085)

Sunflower (FooDB: FOOD00086)
Evening primrose (FooDB: FOOD00120)

Other seed

Quinoa (FooDB: FOOD00441)

Gourd

Tea

Tea products (HMDB: HMDB0002085)

Fat and oil

Olive oil (HMDB: HMDB0002085)

Nut

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Endogenous

Plant

Microbe

Microbe (HMDB: HMDB0002085)
Bifidobacterium (HMDB: HMDB0002085)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0002085)
Antioxidant (HMDB: HMDB0002085)

Biological role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.71 g/L	ALOGPS
logP	1.55	ALOGPS
logP	1.01	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.22 m³·mol⁻¹	ChemAxon
Polarizability	18.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon