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Sigma-Aldrich

Palmatine chloride hydrate

97%

Synonym(s):

5,6-Dihydro-2,3,9,10-tetramethoxydibenzo[a,g]quinolizinium chloride hydrate (1:1:1)

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About This Item

Empirical Formula (Hill Notation):
C21H22ClNO4 · xH2O
CAS Number:
171869-95-7
Molecular Weight:
387.86 (anhydrous basis)
MDL number:
MFCD00150276
UNSPSC Code:
12352100
PubChem Substance ID:
24862239
NACRES:
NA.22

Assay

97%

impurities

~1.5 mol/mol methanol

mp

206-207 °C (dec.) (lit.)

SMILES string

[Cl-].[H]O[H].COc1cc2CC[n+]3cc4c(OC)c(OC)ccc4cc3-c2cc1OC

InChI

1S/C21H22NO4.ClH.H2O/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;;/h5-6,9-12H,7-8H2,1-4H3;1H;1H2/q+1;;/p-1

InChI key

PIQNSCSNSSZUIT-UHFFFAOYSA-M

General description

Palmatine chloride hydrate (Palmatine) is an alkaloid. It is a potential phototoxin, and exhibits low quantum yields for fluorescence. Normal Raman spectra and DFT calculations of palmatine chloride hydrate is reported.

Application

Palmatine chloride hydrate (Palmatine) is suitable for use:
  • as alkaloid standard in the method validation for determination of berberine, hydrastine and canadine in goldenseal (Hydrastis canadensis L.) root powder
  • in the preparation of 8-heteroaryl-7,8-dihydroprotoberberine
  • in a study to investigate the FT-Raman and surface-enhanced Raman scattering (SERS) spectra of three related alkaloid dyes, namely palmatine, jatrorrhizine and coptisine

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H332,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sayaka Shinji et al.
Bioscience, biotechnology, and biochemistry, 84(1), 63-75 (2019-08-30)
A natural isoquinoline alkaloid, berberine, has been known to exhibit anti-tumor activity in various cancer cells via inducing cell cycle arrest. However, it has not been investigated whether berberine and its analogs inhibit the growth of rhabdomyosarcoma (RMS), which is
Surface-enhanced Raman scattering of protoberberine alkaloids.
Canamares MV, et al.
Journal of Raman Spectroscopy, 39(12), 1907-1914 (2008)
Holly A Weber et al.
Journal of AOAC International, 86(3), 476-483 (2003-07-11)
A fast, practical ambient extraction methodology followed by isocratic liquid chromatography (LC) analysis with UV detection was validated for the determination of berberine, hydrastine, and canadine in goldenseal (Hydrastis canadensis L.) root powder. The method was also validated for palmatine
Fluorescence enhancement for alkaloids by anions: Spectroscopic and electrochemical characterizations.
Chung Y-L, et al.
Journal of Electroanalytical Chemistry, 610(1), 85-89 (2007)
Lenka Grycová et al.
Magnetic resonance in chemistry : MRC, 46(12), 1127-1134 (2008-09-11)
Adducts of the quaternary protoberberine alkaloids (QPA) berberine, palmatine, and coptisine were prepared with nucleophiles derived from pyrrole, pyrazole, imidazole, and 1,2,4-triazole. The products, 8-substituted 7,8-dihydroprotoberberines, were identified by mass spectrometry and 1D and 2D NMR spectroscopy, including (1)H--(15)N shift
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