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L-Sulforaphane

$480

  • Brand : BIOFRON

  • Catalogue Number : AV-H12047

  • Specification : 98%

  • CAS number : 142825-10-3

  • Formula : C6H11NOS2

  • Molecular Weight : 177.29

  • PUBCHEM ID : 9577379

  • Volume : 50mg

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Catalogue Number

AV-H12047

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

177.29

Appearance

Brown liquid

Botanical Source

Brassica oleracea L. var. botrytis L/Broccoli seeds

Structure Type

Category

Standards;Natural Pytochemical;API

SMILES

CS(=O)CCCCN=C=S

Synonyms

1-Isothiocyanato-4-(methylsulfinyl)butane/SULFORAPHANE, (±)-/4-Isothiocyanatobutyl methyl sulfoxide/4-Methylsulfinylbutyl isothiocyanate/1-Isothiocyanato-4-[(R)-methylsulfinyl]butane/4-(Methylsulfinyl)butyl isothiocyanate/Butane, 1-isothiocyanato-4-[(R)-(1R)-methylsulfinyl]-/Butane, 1-isothiocyanato-4-(methylsulfinyl)-/(R)-sulforaphane/DL-Sulforaphane/(R)-1-isothiocyanato-4-(methylsulfinyl)butane/Sulforaphane/(-)-Sulforaphane/L-Sulforaphane/4-isothiocyanatobutyl methyl (R)-sulfoxide/(R)-1-Isothiocyanato-4-(methylsulfinyl)butane,4-Methylsulfinylbutyl isothiocyanate/SCN4SO&1

IUPAC Name

1-isothiocyanato-4-[(R)-methylsulfinyl]butane

Applications

(R)-Sulforaphane is a highly potent inducer of the Keap1/Nrf2/ARE pathway. (R)-Sulforaphane is a far more potent inducer of the carcinogen-detoxifying enzyme systems in rat liver and lung than the S-isomer[1][2].

Density

1.2±0.1 g/cm3

Solubility

Flash Point

176.5±23.2 °C

Boiling Point

368.2±25.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:142825-10-3) 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

24871574

Abstract

Dietary R-sulforaphane is a highly potent inducer of the Keap1/Nrf2/ARE pathway. Furthermore, sulforaphane is currently being used in clinical trials to assess its effects against different tumour processes. This study reports an efficient preparation of enantiopure R-sulforaphane based on the enzymatic hydrolysis of its natural precursor glucoraphanin. As an alternative to broccoli seeds, we have exploited Tuscan black kale seeds as a suitable source for gram-scale production of glucoraphanin. The defatted seed meal contained 5.1% (w/w) of glucoraphanin that was first isolated through an anion exchange chromatographic process, and then purified by gel filtration. The availability of glucoraphanin (purity ? 95%, weight basis) has allowed us to develop a novel simple hydrolytic process involving myrosinase (EC 3.2.1.147) in a biphasic system to directly produce R-sulforaphane. In a typical experiment, 1.09 g of enantiopure R-sulforaphane was obtained from 150 g of defatted Tuscan black kale seed meal.

KEYWORDS

R-sulforaphane, Tuscan black kale, Brassica oleracea, glucoraphanin, glucosinolate, biphasic system

Title

Novel Gram-Scale Production of Enantiopure R-Sulforaphane from Tuscan Black Kale Seeds

Author

Gina Rosalinda De Nicola,1,* Patrick Rollin,2 Emanuela Mazzon,3 and Renato Iori1,*

Publish date

2014 May 27

PMID

30420908

Abstract

Nuclear factor- (erythroid-derived 2) like 2 (Nrf2) is a transcription factor that regulates the expression of a battery of antioxidant, anti-inflammatory, and cytoprotective enzymes including heme oxygenase-1 (Hmox1, Ho-1) and NADPH:quinone oxidoreductase-1 (Nqo1). The isothiocyanate sulforaphane (SF) is widely understood to be the most effective natural activator of the Nrf2 pathway. Falcarinol (FA) is a lesser studied natural compound abundant in medicinal plants as well as dietary plants from the Apiaceae family such as carrot. We evaluated the protective effects of FA and SF (5 mg/kg twice per day in CB57BL/6 mice) pretreatment for one week against acute intestinal and systemic inflammation. The phytochemical pretreatment effectively reduced the magnitude of intestinal proinflammatory gene expression (IL-6, Tnfα/Tnfαr, Infγ, STAT3, and IL-10/IL-10r) with FA showing more potency than SF. FA was also more effective in upregulating Ho-1 at mRNA and protein levels in both the mouse liver and the intestine. FA but not SF attenuated plasma chemokine eotaxin and white blood cell growth factor GM-CSF, which are involved in the recruitment and stabilization of first-responder immune cells. Phytochemicals generally did not attenuate plasma proinflammatory cytokines. Plasma and intestinal lipid peroxidation was also not significantly changed 4 h after LPS injection; however, FA did reduce basal lipid peroxidation in the mesentery. Both phytochemical pretreatments protected against LPS-induced reduction in intestinal barrier integrity, but FA additionally reduced inflammatory cell infiltration even below negative control.

Title

Falcarinol Is a Potent Inducer of Heme Oxygenase-1 and Was More Effective than Sulforaphane in Attenuating Intestinal Inflammation at Diet-Achievable Doses

Author

Amanda L. Stefanson and Marica Bakoviccorresponding author

Publish date

2018 Oct 21

PMID

29955088

Abstract

Upon tissue damage the plant secondary metabolites glucosinolates can generate various hydrolysis products, including isothiocyanates (ITCs). Their role in plant defence against insects and pest and their potential health benefits have been well documented, but our knowledge regarding the endogenous molecular mechanisms of their effect in plants is limited. Here we investigated the effect of allyl-isothiocyanate (AITC) on Arabidopsis thaliana mutants impaired in homeostasis of the low-molecular weight thiol glutathione. We show that glutathione is important for the AITC-induced physiological responses, since mutants deficient in glutathione biosynthesis displayed a lower biomass and higher root growth inhibition than WT seedlings. These mutants were also more susceptible than WT to another ITC, sulforaphane. Sulforaphane was however more potent in inhibiting root growth than AITC. Combining AITC with the glutathione biosynthesis inhibitor L-buthionine-sulfoximine (BSO) led to an even stronger phenotype than observed for the single treatments. Furthermore, transgenic plants expressing the redox-sensitive fluorescent biomarker roGFP2 indicated more oxidative conditions during AITC treatment. Taken together, we provide genetic evidence that glutathione plays an important role in AITC-induced growth inhibition, although further studies need to be conducted to reveal the underlying mechanisms.

Title

Arabidopsis mutants impaired in glutathione biosynthesis exhibit higher sensitivity towards the glucosinolate hydrolysis product allyl-isothiocyanate

Author

Janos Urbancsok, Atle M. Bones, and Ralph Kissencorresponding author

Publish date

2018 Jun 28