Silydianin

ChemicalBook > CAS DataBase List > Silydianin

Structure

Product Name: Silydianin
CAS No.: 29782-68-1
Chemical Name: Silydianin
Synonyms: SILIDIANIN;SILYDIANIN;Silydianin，SD;SILYDIANIN(P);Silydianin-RM;SILYDIANIN hplc;Silydianin (20 mg);SILYDIANIN USP/EP/BP;Silydianin, 98%, from Silybum marianum (L.) Gaertn.;(3R,3aR,6R,7aR,8R)-7a-Hydroxy-8-(4-hydroxy-3-methoxyphenyl)-4-((2R,3R)-3,5,7-trihydroxy-4-oxochroman-2-yl)-3,3a,6,7a-tetrahydro-3,6-methanobenzofuran-7(2H)-one
CBNumber: CB7106055
Molecular Formula: C25H22O10
Formula Weight: 482.44
MOL File: 29782-68-1.mol

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Silydianin Property

Melting point:: 191℃
Boiling point:: 819.0±65.0 °C(Predicted)
Density: 1.675±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
form: Solid
pka: 7.41±0.60(Predicted)
color: White to Off-White
Water Solubility: practically insoluble in water

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Safety

Hazard Codes: Xn
Risk Statements: 22
Safety Statements: 22-45
WGK Germany: 3
HS Code: 2932996560

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning
Hazard statements: H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 1612641
Product name: Silydianin
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 30mg
Price: $394
Updated: 2024/03/01

Sigma-Aldrich

Product number: PHL89282
Product name: Silydianin
Purity: phyproof? Reference Substance
Packaging: 10MG
Price: $274
Updated: 2023/06/20

Sigma-Aldrich

Product number: 30494
Product name: Silydianin
Purity: analytical standard
Packaging: 10mg
Price: $568
Updated: 2022/05/15

Usbiological

Product number: 300976
Product name: Silydianin
Packaging: 10mg
Price: $439
Updated: 2021/12/16

TRC

Product number: S465890
Product name: Silydianin
Packaging: 10mg
Price: $340
Updated: 2021/12/16

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Silydianin Chemical Properties,Usage,Production

Structure

The structure of silydianin is unique among flavonolignans and somewhat complicated, but it is biosynthesized analogously to other silymarin flavonolignans - by the radical coupling of taxifolin and coniferyl alcohol. The only substantial difference is in the radical coupling forming two new CeC bonds, creating a bicyclo structure and the fate of the primary alcoholic group of the coniferyl alcohol. In silydianin, intramolecular hemiacetalization occurs; thus, the unusual geminal ketone-hemiacetal structure is formed.
The structure of silydianin was initially resolved using X-ray diffraction data. Since the resolution of the original data was low, the misplacement of some atoms or bonds was possible. Silydianin was crystallized from MeOH, and the crystal was used for X-ray crystallography. The crystallographic data presented here agree with the previously published structure but in a significantly higher resolution (original data d = 1.64 Å, this paper’s data d = 0.82 Å).

Description

Silydianin is a flavonolignan found in S. marianum and has diverse biological activities. It inhibits tyrosinase (IC50 = 2.6 μM for the mushroom enzyme) and scavenges DPPH radicals in a cell-free assay (IC50 = 66.8 μM). Silydianin (100 μM) protects against cytotoxicity induced by allyl alcohol, carbon tetrachloride, paracetamol (acetaminophen), or D-galactosamine in primary human hepatocytes. It inhibits the proliferation of DU145 and PC3 prostate cancer cells when used at a concentration of 90 μM. Silydianin (1%) prevents methacholine-induced airway hyperresponsiveness (AHR) and reduces blood and bronchoalveolar lavage fluid (BALF) levels of eosinophils in an ovalbumin-sensitized mouse model of allergic asthma when administered via inhalation.

Originator

Silydianin was isolated for the first time by G. M schlin during initial experiments with S. marianum fruits as a compound named E5.

Uses

Silydianin is an active constituent of Silybium marianum and is known the exhibit anti-inflammatory activity which regulates caspase-3 activation which affects cell membranes and acts as a free radical scavenger.

Cytotoxicity

Cell suspensions were incubated with different concentrations of silydianin (up to a final concentration of 1–100 μM) for 30 min at 37 °C in a dark incubator and untreated control samples. The samples were then centrifuged at 800–900 rpm, PMNs were resuspended in RPMI 1640, and 0.4% trypan blue and the viable and dead cells were scored. The cell viability was 94.8 ± 3.8% for silydianin at concentrations of 1–100 μM, indicating no cytotoxicity toward neutrophils[2].

References

[1] David Biedermann . “Oxidation of flavonolignan silydianin to unexpected lactone-acid derivative.” Phytochemistry Letters 30 (2019): Pages 14-20.
[2] Ma?gorzata Zielińska-Przyjemska, Krzysztof Wiktorowicz. “An in vitro study of the protective effect of the flavonoid silydianin against reactive oxygen species.” Phytotherapy Research 20 2 (2006): 115–9.

Silydianin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Silydianin manufacturers

Shanghai Standard Technology Co., Ltd.

Product: Silydianin 29782-68-1
Price: US $0.00/mg
Min. Order: 20mg
Purity: ≥98%(HPLC)
Supply Ability: 100 g
Release date: 2020-08-12

Career Henan Chemical Co

Product: SILYDIANIN 29782-68-1
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100KG
Release date: 2020-02-16

29782-68-1, SilydianinRelated Search:

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SILYDIANIN

SILIDIANIN

SILYDIANIN(P)

SILYDIANIN hplc

(3R,8R)-2,3,3aβ,7a-Tetrahydro-7aβ-hydroxy-8-(4-hydroxy-3-methoxyphenyl)-4-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-4-oxo-2H-1-benzopyran-2-yl]-3α,6α-methanobenzofuran-7(6H)-one

Silydianin (20 mg)

3,6-Methanobenzofuran-7(6H)-one,4-[(2R,3R)-3,4-dihydro-3,5,7-trihydroxy-4-oxo-2H-1-benzopyran-2-yl]-2,3,3a,7a-tetrahydro-7a-hydroxy-8-(4-hydroxy-3-methoxyphenyl)-,(3R,3aR,6R,7aR,8R)-

Silydianin, 98%, from Silybum marianum (L.) Gaertn.

Silydianin，SD

SILYDIANIN USP/EP/BP

(3R,3aR,6R,7aR,8R)-7a-Hydroxy-8-(4-hydroxy-3-methoxyphenyl)-4-((2R,3R)-3,5,7-trihydroxy-4-oxochroman-2-yl)-3,3a,6,7a-tetrahydro-3,6-methanobenzofuran-7(2H)-one

Silydianin-RM

29782-68-1

29782-28-1

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

Plant Oils, Toxins, Phenolic Acids & Derivatives