Record Information
Version1.0
Creation date2010-04-08 22:09:45 UTC
Update date2018-05-28 23:31:12 UTC
Primary IDFDB011657
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSyringin
DescriptionSyringin, also known as eleutheroside b or beta-terpineol, is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides 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. Syringin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Syringin can be found in caraway, fennel, and lemon, which makes syringin a potential biomarker for the consumption of these food products. Syringin is a natural chemical compound first isolated from the bark of lilac (Syringa vulgaris) by Meillet in 1841. It has since been found to be distributed widely throughout many types of plants. It is also called eleutheroside B, and is found in Eleutherococcus senticosus (Siberian ginseng). It is also found in dandelion coffee .
CAS Number118-34-3
Structure
Thumb
Synonyms
SynonymSource
4-O-(beta-D-Glucosyl)-trans-4-sinapoyl alcoholChEBI
beta-TerpineolChEBI
Eleutheroside bChEBI
LigustrinChEBI
LilacinChEBI
MAGNOLENIN aChEBI
MethoxyconiferineChEBI
SyriginChEBI
SyringeninChEBI
SyringosideChEBI
4-O-(b-D-Glucosyl)-trans-4-sinapoyl alcoholGenerator
4-O-(Β-D-glucosyl)-trans-4-sinapoyl alcoholGenerator
b-TerpineolGenerator
Β-terpineolGenerator
Sinapyl alcohol 4-O-glucosideMeSH
4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl beta-D-glucopyranosidemanual
Alyposidedb_source
Eleutheroside Bdb_source
Ilexanthin Adb_source
Magnolenindb_source
Magnolenin abiospider
Methoxyconiferindb_source
Syringindb_source
Predicted Properties
PropertyValueSource
Water Solubility3.54 g/LALOGPS
logP-0.32ALOGPS
logP-1.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area138.07 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.24 m³·mol⁻¹ChemAxon
Polarizability37.46 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H24O9
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 IdentifierInChI=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 KeyQJVXKWHHAMZTBY-GCPOEHJPSA-N
Isomeric SMILESCOC1=CC(\C=C\CO)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Average Molecular Weight372.3671
Monoisotopic Molecular Weight372.142032366
Classification
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.83%; H 6.50%; O 38.67%DFC
Melting PointMp 191-192°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -18 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01533
Pubchem Compound ID5316860
Pubchem Substance IDNot Available
ChEBI ID9380
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBQP05-S:GXP64-J
EAFUS IDNot Available
Dr. Duke IDSYRINGIN
BIGG IDNot Available
KNApSAcK IDC00030167
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
adaptogenicDUKE
anti complementaryDUKE
anti pyretic35493 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 stress52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
immunostimulant50847 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
neurotropicDUKE
tonicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).