14215-86-2

Basic information

• Product Name: Sweroside
• Synonyms: SWEROSIDE;(4aS,5R,6S)-5-Ethenyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one;Sweroside, froM Swertia biMaculata;Sweroside, 98%, from Swertia bimaculata (Sieb. & Zucc.) Hook.f. & Thoms. ex C. B. Clarke
• CAS NO: 14215-86-2
• Molecular Formula: C16H22O9
• Molecular Weight: 358.34
• Product Categories: Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 14215-86-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 106～109℃
• Boiling Point: 630.332 °C at 760 mmHg
• Flash Point: 231.791 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 1.55E-18mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: ?20°C
• Solubility: Methanol (Slightly)
• PKA: 12.79±0.70(Predicted)
• CAS DataBase Reference: Sweroside(CAS DataBase Reference)
• NIST Chemistry Reference: Sweroside(14215-86-2)
• EPA Substance Registry System: Sweroside(14215-86-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 14215-86-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Sweroside is used as an anti-inflammatory agent for its ability to reduce inflammation in the body. This property makes it a potential candidate for the development of medications targeting various inflammatory conditions.
Sweroside is also used as an analgesic agent for its pain-relieving capabilities. Its effectiveness in alleviating pain can be utilized in the formulation of drugs aimed at managing acute and chronic pain.
Used in Traditional Medicine:
In traditional medicine, Sweroside is used for its anti-inflammatory and analgesic properties, often as a component in herbal remedies and treatments for various ailments related to inflammation and pain.
Used in Cosmetics Industry:
Sweroside's anti-inflammatory properties can be harnessed in the cosmetics industry for the development of products aimed at reducing skin inflammation and soothing irritated skin, making it a valuable ingredient in skincare formulations.
Used in Nutraceutical Applications:
Due to its beneficial properties, Sweroside can be incorporated into nutraceutical products, such as dietary supplements and functional foods, to support overall health and well-being by providing anti-inflammatory and analgesic benefits.

InChI:InChI=1/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10-,11-,12+,13-,15+,16+/m1/s1

Upstream product

• 19351-28-1 secologanoside 
• 58822-47-2 secoxyloganin 

Downstream Products

• 15215-11-9 Swerosid Aglucon 
• 2280-44-6 D-Glucose 

Relevant articles and documents

Rigenolide A, a new secoiridoid glucoside with a cyclobutane skeleton, and three new acylated secoiridoid glucosides from Gentiana rigescens Franch

Rigenolide A (1), a new secoiridoid glucoside with a cyclobutane skeleton and three new acylated secoiridoid glucosides, 2′-(2,3-dihydroxybenzoyl)- gentiopicroside (2), 2′-(2,3-dihydroxybenzoyl)-swertiamarin (3), 3′-(2,3-dihydroxybenzoyl)-sweroside (4), along with two noriridoids (7 and 8) and two known secoiridoid glucosides (5 and 6), were isolated from Gentiana rigescens Franch. The structures of new compounds were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for DPPH free-radical scavenging activity.

Rhodenthoside A, a new type of acylated secoiridoid glycoside from Gentiana rhodentha

Investigation of the metabolites from Gentiana rhodentha FR. (Gentianaceae) by LC-UV and LC-MS resulted in the isolation and identification of a new type of secoiridoid glycoside, rhodenthoside A (1), together with the known secoiridoids sweroside (2) and swertiamarin (3), as well as the known iridoids kingiside (4) and 8-epikingiside (5). The structures were established by 1D- and 2D-NMR, EI-MS, D/CI-MS, FAB-MS, CF-FAB, LC-MS, TSP, LC-MS, and LD-MS data in combination with chemical reactions.

Camptothecins and two new monoterpene glucosides from Ophiorrhiza liukiuensis

Two new monoterpene glucosides, demethylsecologanol and 3?-O-glucosylsenburiside II, were isolated from Ophiorrhiza liukiuensis (Rubiaceae) together with 23 known compounds, including camptothecins and β-carboline-type alkaloids. Their structures were determined by spectroscopic analysis.

NATURAL PRODUCTS CHEMISTRY: A SORT OF HETEROCYCLIC CHEMISTRY

Basic deglucosylation of secoiridoids has been investigated on sweroside and its derivatives as model compounds.The deglucosylation was carried out by propylamine and piperidine and in both cases the amine incorporated into the secoiridoid derivative.With propylamine, sweroside 1 and 8,10-dihydrosweroside 2 gave the aza analogue 4 and 5 respectively, however, from 2 a second bridged product 6 was formed, too, which could be obtained from the aglucone 3 as well.The incorporation of piperidine took place at C-1 of 7 in the case of glucoside sweroside 1, but at C-3- of 9 in the case of aglucone 3 of 8,10-dihydrosweroside 2.

SYNTHESIS OF THE MONOTERPENE ALKALOID BAKANKOSIN FROM SECOLOGANIN

Reduction of secologanin 1a with sodium borohydride followed by acylation afforded 86percent of sweroside tetraacetate 4 which was transformed to the 8-iodomethylester 5c by treatment with trimethylsilyliodide, hydrolysis and addition of diazomethane in 9