Showing Compound Syringin (FDB011657)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:45 UTC

Update date

2025-11-18 23:29:57 UTC

Primary ID

FDB011657

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Syringin

Description

Syringin, also known as eleutheroside B or lilacin, was first isolated from the bark of lilac (Syringa vulgaris) by Meillet in 1841, where its name likely was derived. It belongs to the class of organic compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Syringin results from the glycosidic bonding of sinapyl alcohol and glucose. Some examples of phenolic structures include lignans and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Syringin is neutral compound. Syringin is a naturally occurring organic compound found in many plants such as Eleutherococcus senticosus (Siberian ginseng), dandelion, coffee. Syringin has also been detected in caraway, fennels, and lemons ( http://www.thegoodscentscompany.com/data/rw1466551.html#tooccur). Syringin have been reported to have immunomodulatory, anti-inflammatory, antinociceptive and hypoglucemic effects (PMID: 11578112; PMID: 15549657; PMID: 18203055).

CAS Number

118-34-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-O-(beta-D-Glucosyl)-trans-4-sinapoyl alcohol	ChEBI
beta-Terpineol	ChEBI
Eleutheroside b	ChEBI
Ligustrin	ChEBI
Lilacin	ChEBI
MAGNOLENIN a	ChEBI
Methoxyconiferine	ChEBI
Syrigin	ChEBI
Syringenin	ChEBI
Syringoside	ChEBI
4-O-(b-D-Glucosyl)-trans-4-sinapoyl alcohol	Generator
4-O-(Β-D-glucosyl)-trans-4-sinapoyl alcohol	Generator
b-Terpineol	Generator
Β-terpineol	Generator
Sinapyl alcohol 4-O-glucoside	MeSH
4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl beta-D-glucopyranoside	manual
Alyposide	db_source
Eleutheroside B	db_source
Ilexanthin A	db_source
Magnolenin	db_source
Magnolenin a	biospider
Methoxyconiferin	db_source
Syringin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	3.54 g/L	ALOGPS
logP	-0.32	ALOGPS
logP	-1.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	138.07 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.24 m³·mol⁻¹	ChemAxon
Polarizability	37.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H24O9

IUPAC name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenoxy}oxane-3,4,5-triol

InChI Identifier

InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1

InChI Key

QJVXKWHHAMZTBY-GCPOEHJPSA-N

Isomeric SMILES

COC1=CC(\C=C\CO)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Average Molecular Weight

372.3671

Monoisotopic Molecular Weight

372.142032366

Classification

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Cinnamyl alcohol
Dimethoxybenzene
M-dimethoxybenzene
Methoxybenzene
Anisole
Phenoxy compound
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Oxacycle
Ether
Acetal
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:9380 )
monosaccharide derivative (CHEBI:9380 )
primary alcohol (CHEBI:9380 )
dimethoxybenzene (CHEBI:9380 )
Sinapate derivatives (C01533 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 54.83%; H 6.50%; O 38.67%	DFC
Melting Point	Mp 191-192°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -18 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Syringin, TMS_3_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-03di-0900000000-f96467539c41172c0acc	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-01ox-0921000000-3679abcaaec44614df3f	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-03ec-0930000000-ab5d3b3faf244f842569	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-01si-0920000000-d6ca8e518f6c19045356	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-0002-0019000000-428ad645054e7ec9123a	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-004j-0098000000-68e6082813f13e72653d	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-0ue9-0190000000-7abbfb70a416aeca380c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-03di-0900000000-9332b89759063c39867d	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08ml-0649000000-1dc5fb5d7d622ccf233c	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-0921000000-8261eb2a00fd30f2bd1c	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-2910000000-b3bc64b5eea585f493dd	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-1449000000-aebf03ec38a4451f44c6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6u-0932000000-e6cc56d8d4b8a740f13e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-3910000000-69c5b29e4a9ee146dd5a	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

9380

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BQP05-S:GXP64-J

EAFUS ID

Not Available

Dr. Duke ID

SYRINGIN

BIGG ID

Not Available

KNApSAcK ID

C00030167

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Syringin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Knapsack: C00000010

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Angiotensin converting enzyme inhibitor	35457	An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.	DUKE
Adaptogenic		A substance that stabilizes physiological processes, promoting homeostasis by decreasing cellular sensitivity to stress, used therapeutically to manage anxiety, fatigue, and stress-related disorders.	DUKE
Anti complementary		A substance that diminishes or abolishes the action of a complement, playing a role in regulating the immune system. Therapeutically, it's used to prevent excessive inflammation and tissue damage. Key medical uses include treating autoimmune disorders, transplant rejection, and inflammatory diseases.	DUKE
Anti pyretic	35493	An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.	DUKE
Anti-stress	52217	An agent that reduces stress symptoms, commonly used in managing anxiety disorders, promoting relaxation, and mitigating the biological effects of stress on the body, such as hypertension and immune suppression, with therapeutic applications in mental health and key medical uses in cardiology and neurology.	DUKE
Immunomodulator	50846	An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.	DUKE
Immunostimulant	50847	An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.	DUKE
Neurotropic		An agent that targets the nervous system, affecting neurons and neural tissues. Its biological role involves altering neural function, with therapeutic applications in treating neurological disorders. Key medical uses include gene therapy, cancer treatment, and neuroregeneration, where neurotropic agents can deliver therapeutic genes or toxins to specific neural cells.	DUKE
Tonic		A physiological response that is slow and graded, playing a crucial role in maintaining muscle tone and sensory perception. Therapeutically, tonics are used to enhance muscle strength and endurance, while also having applications in managing conditions such as muscle spasms and sensory disorders, promoting overall physiological balance and stability.	DUKE