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syringin
4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl-b-D-glucopyranoside

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Name:(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
CAS Number: 118-34-3Picture of molecule3D/inchi
Other(deleted CASRN):55598-67-9
FDA UNII: I6F5B11C96
Nikkaji Web:J246.058K
Beilstein Number:097166
MDL:MFCD00016778
XlogP3:-1.30 (est)
Molecular Weight:372.37108000
Formula:C17 H24 O9
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 642.58 °C. @ 760.00 mm Hg (est)
Flash Point: 648.00 °F. TCC ( 342.40 °C. ) (est)
logP (o/w): -1.550 (est)
Soluble in:
 water, 4.961e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Eleutheroside B 98%
BOC Sciences
For experimental / research use only.
Eleutheroside B
Carbosynth
For experimental / research use only.
Syringin
Glentham Life Sciences
Syringin
Santa Cruz Biotechnology
For experimental / research use only.
Eleutheroside B
Sigma-Aldrich
For experimental / research use only.
Eleutheroside B
analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for syringin usage levels up to:
 not for fragrance use.
 
Recommendation for syringin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5316860
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
Chemidplus:0000118343
 
References:
 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5316860
Pubchem (sid):135030310
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
KEGG (GenomeNet):C01533
HMDB (The Human Metabolome Database):Search
FooDB:FDB011657
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 caraway
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 centaurea cineraria
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 centaurea napifolia
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 fennel
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 lemon pericarp
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 syringa reticulata
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 viscum coloratum
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Synonyms:
(2S,3R,4S,5S,6R)-2-[2,6-dimethoxy-4-[(E)-3-oxidanylprop-1-enyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
 eleutheroside B
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl b-D-glucopyranoside
4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl-b-D-glucopyranoside
4-(3-hydroxypropenyl)-2,6-dimethoxyphenyl dextro-glucoside
4-(3-hydroxypropenyl)-2,6-dimethoxyphenyl-D-glucoside
 ligustrin
 lilacin
 magnolenin A
 methoxyconiferine
 syrigin
 syringenin
 syringinenin
 syringoside
 

Articles:

PubMed:Enzymatic and metabolic engineering for efficient production of syringin, sinapyl alcohol 4-O-glucoside, in Arabidopsis thaliana.
PubMed:Three new lignan glycosides with IL-6 inhibitory activity from Akebia quinata.
PubMed:Soluble phenylpropanoids are involved in the defense response of Arabidopsis against Verticillium longisporum.
PubMed:[Chemical constituents from whole plants of Aconitum tanguticum].
PubMed:[Chemical constituents from stems of Cistanche deserticola cultured in Tarim desert].
PubMed:[Chemical constituents from whole plants of Carduus acanthoides].
PubMed:A new tetrahydrofuran lignan diglycoside from Viola tianshanica Maxim.
PubMed:An LC-MS/MS method for determination of curculigoside with anti-osteoporotic activity in rat plasma and application to a pharmacokinetic study.
PubMed:Metabolic engineering of the phenylpropanoid pathway enhances the antioxidant capacity of Saussurea involucrata.
PubMed:Effects of cocktail of four local Malaysian medicinal plants (Phyllanthus spp.) against dengue virus 2.
PubMed:Development of sample preparation method for eleutheroside B and E analysis in Acanthopanax senticosus by ionic liquids-ultrasound based extraction and high-performance liquid chromatography detection.
PubMed:Crude extract and purified components isolated from the stems of Tinospora crispa exhibit positive inotropic effects on the isolated left atrium of rats.
PubMed:Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay.
PubMed:Chemical constituents from Dendropanax dentiger.
PubMed:Characterization of phenolic constituents from ephedra herb extract.
PubMed:Hepatoprotective effects of syringin on fulminant hepatic failure induced by D-galactosamine and lipopolysaccharide in mice.
PubMed:Isolation of phenolic compounds from iceberg lettuce and impact on enzymatic browning.
PubMed:Simultaneous determination of Eleutheroside B and Eleutheroside E in rat plasma by high performance liquid chromatography-electrospray ionization mass spectrometry and its application in a pharmacokinetic study.
PubMed:Qualitative and quantitative analysis of phenylpropanoids in cell culture, regenerated plantlets and herbs of Saussurea involucrata.
PubMed:Down-regulation of the caffeic acid O-methyltransferase gene in switchgrass reveals a novel monolignol analog.
PubMed:Impact of the absence of stem-specific β-glucosidases on lignin and monolignols.
PubMed:Enrichment and Purification of Syringin, Eleutheroside E and Isofraxidin from Acanthopanax senticosus by Macroporous Resin.
PubMed:Ultrasound-Assisted Extraction of Syringin from the Bark of Ilex rotunda Thumb Using Response Surface Methodology.
PubMed:Metabolite profiling of jaboticaba (Myrciaria cauliflora) and other dark-colored fruit juices.
PubMed:Simultaneous quantification of five bioactive components of Acanthopanax senticosus and its extract by ultra performance liquid chromatography with electrospray ionization time-of-flight mass spectrometry.
PubMed:Immunomodulatory active compounds from Tinospora cordifolia.
PubMed:Characterization of eleutheroside B metabolites derived from an extract of Acanthopanax senticosus Harms by high-resolution liquid chromatography/quadrupole time-of-flight mass spectrometry and automated data analysis.
PubMed:[One new lignan glycoside from whole plants of Senecio chrysanthemoides].
PubMed:[Chemical constituents from Exochorda racemosa].
PubMed:Janceolaroside A and janceoside A, two new compounds from the stems and roots of Jasminum lanceolarium.
PubMed:[Study on the chemical constituents of Codonopsis lanceolata].
PubMed:[Simultaneous determination of five glycosides in Aidi injection by RP-HPLC-ELSD].
PubMed:[Chemical constituents from aerial part of Atractylodes macrocephala].
PubMed:Three new flavonoid glycosides, byzantionoside B 6'-O-sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula.
PubMed:Simultaneous quantification of polyherbal formulations containing Rhodiola rosea L. and Eleutherococcus senticosus Maxim. using rapid resolution liquid chromatography (RRLC).
PubMed:Acanthopanax senticosus: review of botany, chemistry and pharmacology.
PubMed:[Therapeutic effect of syringin on adjuvant arthritis in rats and its mechanisms].
PubMed:Active components from Siberian ginseng (Eleutherococcus senticosus) for protection of amyloid β(25-35)-induced neuritic atrophy in cultured rat cortical neurons.
PubMed:[Comparison of rutin and syringin content between tissue culturing seedlings and botanical drug of Saussurea involucrata].
PubMed:[Studies on the chemical constituents of Pachysandra terminalis and their antioxidant activity].
PubMed:[Studies on the chemical constituents from the stems of Acanthopanax gracilistylus].
PubMed:Peroxyl radical scavenging capacity of extracts and isolated components from selected medicinal plants.
PubMed:Syringin from stem bark of Fraxinus rhynchophylla protects Abeta(25-35)-induced toxicity in neuronal cells.
PubMed:Chemical constituents from the cell cultures of Saussurea involucrata.
PubMed:Aporphine alkaloids, clerodane diterpenes, and other constituents from Tinospora cordifolia.
PubMed:[Chemical constituents from leaves of Albizia chinensis].
PubMed:[Effect of several penetration enhancers on transdermal absorption in vitro of syringin, chologenic acid and rutin in Xuelian cataplasm].
PubMed:[Studies on chemical constituents from roots of Peucedanum praeruptorum III].
PubMed:[Isolation and analysis of syringin in cell suspension cultures of Saussurea involucrata].
PubMed:[Determination of eleutheroside B in antifatigue fraction of Acanthopanax senticosus by HPLC].
PubMed:[Studies on chemical constituents of aerial parts of Ammopiptanthus mongolicus].
PubMed:[A new 8-O-4' neolignan from Glehnia littoralis].
PubMed:[Studies on chemical constituents of Syringa veutina].
PubMed:Role of sympathetic tone in the loss of syringin-induced plasma glucose lowering action in conscious Wistar rats.
PubMed:[Studies on chemical constituents of Saussurea laniceps].
PubMed:Authentication of the traditional medicinal plant Eleutherococcus senticosus by DNA and chemical analyses.
PubMed:Qualitative evaluation and quantitative determination of 10 major active components in Carthamus tinctorius L. by high-performance liquid chromatography coupled with diode array detector.
PubMed:Release of acetylcholine by syringin, an active principle of Eleutherococcus senticosus, to raise insulin secretion in Wistar rats.
PubMed:Hypoglycemic effect of syringin from Eleutherococcus senticosus in streptozotocin-induced diabetic rats.
PubMed:Increase of beta-endorphin secretion by syringin, an active principle of Eleutherococcus senticosus, to produce antihyperglycemic action in type 1-like diabetic rats.
PubMed:HPLC method for preliminary analysis of constituents in rat blood after oral administration of the extract of Acanthopanax senticosus.
PubMed:Lignan and terpene constituents from the aerial parts of Saussurea pulchella.
PubMed:Simultaneous determination of harpagoside and cinnamic acid in rat plasma by high-performance liquid chromatography: application to a pharmacokinetic study.
PubMed:[The chemical constituents of Polygala hongkongensis Hemsl].
PubMed:Antitumor activities of extracts and compounds from the roots of Daphne tangutica Maxim.
PubMed:(+)-Syringaresinol-di-O-beta-D-glucoside, a phenolic compound from Acanthopanax senticosus Harms, suppresses proinflammatory mediators in SW982 human synovial sarcoma cells by inhibiting activating protein-1 and/or nuclear factor-kappaB activities.
PubMed:A new lignan glycoside from the stem bark of Styrax japonica S. et Z.
PubMed:Two new flavanone glycosides of Jasminum lanceolarium and their anti-oxidant activities.
PubMed:[Studies on chemical constituents of Acroptilon repens].
PubMed:Antioxidant and lipophilic constituents of Tinospora crispa.
PubMed:Water-soluble phenolic glycosides from the whole plant of Bulbophyllum odoratissimum.
PubMed:Cytotoxic constituents from Anagyris foetida leaves.
PubMed:Determination and pharmacokinetic study of syringin and chlorogenic acid in rat plasma after administration of Aidi lyophilizer.
PubMed:PTP1B inhibitors from Saussrurea lappa.
PubMed:Arabidopsis thaliana beta-Glucosidases BGLU45 and BGLU46 hydrolyse monolignol glucosides.
PubMed:Salicylic acid enhances Jaceosidin and Syringin production in cell cultures of Saussurea medusa.
PubMed:[Studies on chemical constituents from roots of Polygala tricornis].
PubMed:Simultaneous determination of protocatechuic acid, syringin, chlorogenic acid, caffeic acid, liriodendrin and isofraxidin in Acanthopanax senticosus Harms by HPLC-DAD.
PubMed:Determination of eleutheroside E and eleutheroside B in rat plasma and tissue by high-performance liquid chromatography using solid-phase extraction and photodiode array detection.
PubMed:Stimulating effect of adaptogens: an overview with particular reference to their efficacy following single dose administration.
PubMed:A comparison between hairy root cultures and wild plants of Saussurea involucrata in phenylpropanoids production.
PubMed:Application of bioreactor system for large-scale production of Eleutherococcus sessiliflorus somatic embryos in an air-lift bioreactor and production of eleutherosides.
PubMed:Furofuran lignans from a callus culture of Cichorium intybus.
PubMed:Quality control of roots of Eleutherococcus senticosus by HPLC.
PubMed:New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica.
PubMed:Lignification in poplar plantlets fed with deuterium-labelled lignin precursors.
PubMed:Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin.
PubMed:Preparative isolation and purification of syringin and edgeworoside C from Edgeworthia chrysantha Lindl by high-speed counter-current chromatography.
PubMed:Light induces phenylpropanoid metabolism in Arabidopsis roots.
PubMed:Anti-oxidant activities of Acanthopanax senticosus stems and their lignan components.
PubMed:Metabolites of orally administered Magnolia officinalis extract in rats and man and its antidepressant-like effects in mice.
PubMed:Phenylpropanoid glycosides of Gnidia polycephala.
PubMed:Bioactive phenolics from Carthamus lanatus L.
PubMed:[Studies on the chemical constituents of Cirsium japonicum DC].
PubMed:[Studies on the phenylpropanoids from Eucommia ulmoides].
PubMed:Acylated phenolic glycosides from Solenostemma argel.
PubMed:[Studies on the chemical constituents of Viscum coloratum].
PubMed:[Determination of syringin and rutin in 11 species of Saussurea by high performance liquid chromatography].
PubMed:Molecular modeling of syringyl and p-hydroxyphenyl beta-O-4 dimers. Comparative study of the computed and experimental conformational properties of lignin beta-O-4 model compounds.
PubMed:A new pyrroloquinazoline alkaloid from Linaria vulgaris.
PubMed:Anti-platelet effect of the constituents isolated from the barks and fruits of Magnolia obovata.
PubMed:Phenolic glucosides from Oxytropis myriophylla.
PubMed:Two new steroids from Adenophora stenanthina subsp. xifengensis.
PubMed:Quantitative determination of eleutheroside B and E from Acanthopanax species by high performance liquid chromatography.
PubMed:[Comparative study of immunomodulating effects of natural experimental preparations on phagocytosis of Yersinia pseudotuberculosis].
PubMed:In-vitro and in-vivo immunomodulatory effects of syringin.
PubMed:Phenylpropanoid glucosides from Chrozophora obliqua.
PubMed:Effects of constituents from the bark of Magnolia obovata on nitric oxide production in lipopolysaccharide-activated macrophages.
PubMed:Lignan and phenylpropanoid glycosides from Phillyrea latifolia and their in vitro anti-inflammatory activity.
PubMed:Immunopharmacological in vitro effects of Eleutherococcus senticosus extracts.
PubMed:Iridoid and megastigmane glycosides from Phlomis aurea.
PubMed:Induction of apoptosis by Acanthopanax senticosus HARMS and its component, sesamin in human stomach cancer KATO III cells.
PubMed:Studies on the vascular effects of the fractions and phenolic compounds isolated from Viscum album ssp. album.
PubMed:Further sesquiterpenoids and phenolics from Taraxacum officinale.
PubMed:Glycosidic fraction of flue-cured tobacco leaves: its separation and component analysis.
PubMed:Studies on constituents with cytotoxic activity from the stem bark of Syringa velutina.
PubMed:Metabolism of liriodendrin and syringin by human intestinal bacteria and their relation to in vitro cytotoxicity.
PubMed:The effect of Kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan.
PubMed:Pharmacological activity of phenylpropanoids of the mistletoe, Viscum album L., host: Pyrus caucasica Fed.
PubMed:Immunopotentiating compounds from Tinospora cordifolia.
PubMed:Syringin 4-O-beta-glucoside, a new phenylpropanoid glycoside, and costunolide, a nitric oxide synthase inhibitor, from the stem bark of Magnolia sieboldii.
PubMed:A beta-glucosidase from lodgepole pine xylem specific for the lignin precursor coniferin.
PubMed:Promotion of neuronal differentiation of PC12h cells by natural lignans and iridoids.
PubMed:[Determination of syrigin in zengzhi granule by HPLC].
PubMed:[Studies on constituents of Ilex chinensis Sims].
PubMed:Two phenethyl alcohol glycosides from Scutellaria orientalis subsp. pinnatifida.
PubMed:[Chemical constituents from stems of Oplopanax elatus Nakai].
PubMed:[Chemical constituents of the root of Oplopanax elatus Nakai].
PubMed:[Studies on the chemical components of Viscum coloratum. VIII. Isolation and structure of 3-beta-D-glucopyranosyloxy-butanol-2].
PubMed:Sesquiterpene lactones and other constituents from a cytotoxic extract of Michelia floribunda.
PubMed:Medicinal protection with Chinese herb-compound against radiation damage.
PubMed:Phenolic compounds from stem bark of Acanthopanax senticosus and their pharmacological effect in chronic swimming stressed rats.
PubMed:Exclusive accumulation of Z-isomers of monolignols and their glucosides in bark of Fagus grandifolia.
PubMed:Phenylpropanes and lignans of Viscum album cardioactive drugs V.
PubMed:[Determination of syringin in Acanthopanax senticosus by HPLC].
PubMed:Studies on the standardization of mistletoe preparations.
PubMed:Phenolic glycosides of Paulownia tomentosa bark.
PubMed:[Isolation and identification of a hemostatic constituent from Chinese drug-jiu bi ying, the bark of Ilex rotund A Thunb (author's transl)].
 
Notes:
a phenylpropanoid glycoside.
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