118-34-3

Basic information

• Product Name: ELEUTHEROSIDE B
• Synonyms: SYRINGIN;SYRINGINE;SYRINGOSIDE;LIGUSTRIN;ILACIN;ELEUTHEROSIDE B;Ciwujianoside-B(ELEUTHEROSIDE B);Syringin (eleutheroside B)
• CAS NO: 118-34-3
• Molecular Formula: C₁₇H₂₄O₉
• Molecular Weight: 372.37
• EINECS: 202-680-6
• Product Categories: Cardioglycosides & Glycosides;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Standardized plant extract;Phenylpropanoids
• Mol File: 118-34-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 192°C
• Boiling Point: 421.84°C (rough estimate)
• Flash Point: 342.4 °C
• Appearance: /
• Density: 1.2870 (rough estimate)
• Vapor Pressure: 2.17E-17mmHg at 25°C
• Refractive Index: 1.6230 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
• PKA: 12.75±0.70(Predicted)
• BRN: 97166
• CAS DataBase Reference: ELEUTHEROSIDE B(CAS DataBase Reference)
• NIST Chemistry Reference: ELEUTHEROSIDE B(118-34-3)
• EPA Substance Registry System: ELEUTHEROSIDE B(118-34-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 118-34-3(Hazardous Substances Data)

Usage

Description

Syringin is a phenylpropanoid glycoside first isolated from A. senticosus that enhances acetylcholine release in pancreatic cells leading to an increase in insulin release through the muscarinic M3 receptor. Syringin dose-dependently (50, 75, and 100 μg/kg, i.v.) decreases plasma glucose levels and increases insulin-like immunoreactivity and C-peptide in rats, and these effects last at least 60 minutes. In a rat model of type 1 diabetes, it decreases plasma glucose and increases β-endorphin release from the adrenal medulla. Syringin increases autophagy through AMP-activated protein kinase α (AMPKα) activation concomitant with preventing the progression of cardiac hypertrophy in mice following aortic banding. It also has immunomodulatory effects, likely due to its metabolite sinapyl alcohol.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 118-34-3 differently. You can refer to the following data:
1. Syringin is a chemical that is found naturally in various plants such as Araliaceae, a adaptogenic agent with Syringin as the active componet. Syringin have exhibited the ability to enhance glucose ut ilization and the lowering of plasma glucose level in rats suffering from insulin deficiency, suggesting that this chemical may be useful in the treatment of human diabetes.
2. Syringin is a chemical that is found naturally in various plants such as Araliaceae, a adaptogenic agent with Syringin as the active componet. Syringin have exhibited the ability to enhance glucose utilization and the lowering of plasma glucose level in rats suffering from insulin deficiency, suggesting that this chemical may be useful in the treatment of human diabetes.

InChI:InChI=1/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

Upstream product

• 203179-62-8 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde 
• 20675-96-1 trans-sinapyl alcohol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 117278-74-7 tangshenoside I 
• 154461-65-1 sinapyl aldehyde 4-O-β-D-glucopyranoside 
• 203179-64-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 83-87-4 D-glucose pentaacetate 
• 117685-21-9 3,5-dimethoxy-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzaldehyde 
• 134-96-3 syringic aldehyde 
• 4206-58-0 (E)-sinapinaldehyde 
• 133-89-1 UDP-glucose 
• 20675-96-1 Syringenin 
• 41628-47-1 ethyl (2E)-3-[4-hydroxy-3,5-bis(methyloxy)phenyl]-2-propenoate 

Downstream Products

• 50-99-7 D-glucose 
• 20675-96-1 trans-sinapyl alcohol 
• 20675-96-1 Syringenin 
• 92233-55-1 syringin penta-acetate 

Related news

Research paperDetermination of eleutheroside E and ELEUTHEROSIDE B (cas 118-34-3) in rat plasma and tissue by high-performance liquid chromatography using solid-phase extraction and photodiode array detection08/26/2019

A HPLC method with photodiode array detection (PDA) was developed for the determination and a pharmacokinetic study of eleutheroside E (ELU E) and eleutheroside B (ELU B) in rat plasma and tissue following an eleutherococcus injection. The analysis was performed on a Kromasil C18 column, using w...detailed

Relevant articles and documents

Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues

Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.

Oxidation of monolignols by members of the berberine bridge enzyme family suggests a role in plant cell wall metabolism

Plant genomes contain a large number of genes encoding for berberine bridge enzyme (BBE)-like enzymes. Despite the wide-spread occurrence and abundance of this protein family in the plant kingdom, the biochemical function remains largely unexplored. In this study, we have expressed two members of the BBE-like enzyme family from Arabidopsis thaliana in the host organism Komagataella pastoris. The two proteins, termed AtBBE-like 13 and AtBBE-like 15, were purified, and their catalytic properties were determined. In addition, AtBBE-like 15 was crystallized and structurally characterized by x-ray crystallography. Here, we show that the enzymes catalyze the oxidation of aromatic allylic alcohols, such as coumaryl, sinapyl, and coniferyl alcohol, to the corresponding aldehydes and that AtBBE-like 15 adopts the same fold as vanillyl alcohol oxidase as reported previously for berberine bridge enzyme and other FAD-dependent oxidoreductases. Further analysis of the substrate range identified coniferin, the glycosylated storage form of coniferyl alcohol, as a substrate of the enzymes, whereas other glycosylated monolignols were rather poor substrates. A detailed analysis of the motifs present in the active sites of the BBE-like enzymes in A. thaliana suggested that 14 out of 28 members of the family might catalyze similar reactions. Based on these findings, we propose a novel role of BBE-like enzymes in monolignol metabolism that was previously not recognized for this enzyme family.

Coniferyl alcohol metabolism in conifers - I. Glucosidic turnover of cinnamyl aldehydes by UDPG: Coniferyl alcohol glucosyltransferase from pine cambium

UDPG: coniferyl alcohol glucosyltransferase (CAGT; EC 2.4.1.111) isolated from cambial tissues of Pinus strobus was able to convert cinnamyl aldehydes as well as dihydroconiferyl alcohol into their corresponding 4-O-β-D-glucosides in vitro, Cinnamyl aldeh