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Schizandriside

$1,268

  • Brand : BIOFRON

  • Catalogue Number : AV-S05571

  • Specification : 96%

  • CAS number : 71222-06-5

  • Formula : C25H32O10

  • Molecular Weight : 492.52

  • PUBCHEM ID : 14521043

  • Volume : 5mg

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Catalogue Number

AV-S05571

Analysis Method

HPLC,NMR,MS

Specification

96%

Storage

2-8°C

Molecular Weight

492.52

Appearance

Powder

Botanical Source

Rhodiola

Structure Type

Lignans

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C2C(C(C(CC2=C1)CO)COC3C(C(C(CO3)O)O)O)C4=CC(=C(C=C4)O)OC)O

Synonyms

β-D-Xylopyranoside, [(1S,2R,3R)-1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-2-naphthalenyl]methyl/[(1S,2R,3R)-7-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl β-D-xylopyranoside

IUPAC Name

(2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol

Applications

1142

Density

1.5±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

394.8±32.9 °C

Boiling Point

729.2±60.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C25H32O10/c1-32-20-6-12(3-4-17(20)27)22-15-8-18(28)21(33-2)7-13(15)5-14(9-26)16(22)10-34-25-24(31)23(30)19(29)11-35-25/h3-4,6-8,14,16,19,22-31H,5,9-11H2,1-2H3/t14-,16-,19+,22-,23-,24+,25+/m0/s1

InChl Key

TXSJJCSJHIDTDE-JTVAWUQMSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:71222-06-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29508253

Abstract

Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca by monitoring antioxidative activity using the 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Starting from a tandem Michael-aldol reaction, the lignan skeleton was synthesized in 6 steps, including a cyclization step. To determine the stereochemistry of 1, we synthesized the natural product (±)-isolariciresinol (18) from alcohol 17. Comparison of the spectral data showed good agreement. Glycosylation was investigated using four different glycosyl donors. Only the Koenigs-Knorr condition using silver trifluoromethanesulfonate with 1,1,3,3-tetramethylurea provided the glycosylated product. Deprotection and purification using reverse-phase high-performance liquid chromatography gave schizandriside (1) and its diastereomer saracoside (2). Synthesized 1, 2 and 18 showed antioxidant activity with IC50 = 34.4, 28.8, 53.0 μM, respectively.

KEYWORDS

Antioxidant activity; Lignan glycoside; Natural product; Total synthesis

Title

Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities.

Author

Sampei M1, Arai MA2, Ishibashi M3.

Publish date

2018 Jun