Showing Compound Syringin (FDB011657)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:45 UTC

Update date

2020-09-17 15:31:32 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

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Synonym	Source
4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl beta-D-glucopyranoside	manual
4-O-(b-D-Glucosyl)-trans-4-sinapoyl alcohol	Generator
4-O-(beta-D-Glucosyl)-trans-4-sinapoyl alcohol	ChEBI
4-O-(Β-D-glucosyl)-trans-4-sinapoyl alcohol	Generator
Alyposide	db_source
b-Terpineol	Generator
beta-Terpineol	ChEBI
Eleutheroside b	ChEBI
Eleutheroside B	db_source
Ilexanthin A	db_source

Showing 1 to 10 of 23 entries

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

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

Showing 1 to 10 of 14 entries

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

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C01533

Pubchem Compound ID

5316860

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

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Knapsack: C00000010

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Caraway	Expected but not quantified	Not Available	KNAPSACK
Fennel	Expected but not quantified	Not Available	KNAPSACK
Lemon	Expected but not quantified	Not Available	DUKE

Showing 1 to 3 of 3 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
adaptogenic			DUKE
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
anti complementary			DUKE
anti pyretic	35493	A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.	DUKE
anti stress	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
immunomodulator	50846	Biologically active substance whose activity affects or plays a role in the functioning of the immune system.	DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
neurotropic			DUKE
tonic			DUKE