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H2751

(1R,9S)-(−)-β-Hydrastine

Name: (1R,9S)-(−)-β-Hydrastine
Brand: SIGMA

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₁NO₆

CAS Number:

118-08-1

Molecular Weight:

383.39

EC Number:

204-233-0

MDL number:

MFCD00152561

UNSPSC Code:

12352200

PubChem Substance ID:

24895532

storage temp.

−20°C

SMILES string

CN1CCC2=CC3=C(OCO3)C=C2[C@]1([H])[C@@]4(C(C=CC(OC)=C5OC)=C5C(O4)=O)[H]

InChI

1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m1/s1

InChI key

JZUTXVTYJDCMDU-MOPGFXCFSA-N

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Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine.

J J Inbaraj et al.

Chemical research in toxicology, 19(6), 739-744 (2006-06-20)

Goldenseal is an herb that is widely used in dietary supplements, eye washes, and skin lotions. The presence of Goldenseal root powder in dietary supplements and the topical application of Goldenseal preparations raise the possibility that an adverse phototoxic reaction

Variations in alkaloid content of herbal products containing goldenseal.

David J Edwards et al.

Journal of the American Pharmacists Association : JAPhA, 43(3), 419-423 (2003-07-03)

To determine the concentration of hydrastine and berberine, the primary alkaloids in herbal products containing goldenseal. Descriptive comparison of 20 products purchased at local pharmacies or health food stores; 17 products were labeled as containing goldenseal root and 3 products

Enantio-selective inhibition of (1R,9S)- and (1S,9R)-beta-hydrastines on dopamine biosynthesis in PC12 cells.

Shou Yu Yin et al.

Neuropharmacology, 47(7), 1045-1052 (2004-11-24)

The inhibitory effects of (1R,9S)- and (1S,9R)-enantiomers of beta-hydrastine (BHS) on dopamine biosynthesis in PC12 cells were investigated. (1R,9S)-BHS decreased the intracellular dopamine content with the IC50 value of 14.3 microM at 24 h, but (1S,9R)-BHS did not. (1R,9S)-BHS was

Capillary zone electrophoresis as a tool for the quality control of goldenseal extracts.

Matthias Unger et al.

Electrophoresis, 26(12), 2430-2436 (2005-05-25)

The root extracts of goldenseal (Hydrastis canadensis L.) are popular phytomedicines for the treatment of gastrointestinal disorders and upper respiratory tract infections. Here we describe a simple and fast capillary zone electrophoresis (CZE) method with ultraviolet detection at 225 nm

A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis.

Catherine E McNamara et al.

Journal of natural products, 67(11), 1818-1822 (2004-12-01)

A new compound, 5-O-(4'-[beta-d-glucopyranosyl]-trans-feruloyl)quinic acid (GPFQ, 10), is reported from the medicinal plant goldenseal (Hydrastis canadensis). A new HPLC method is described and used to show that GPFQ is a potential marker for goldenseal roots (1.0% w/w) and rhizomes (2.3%).

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