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Merck
CN

37033

Seneciphylline

analytical standard

Synonym(s):

α-Longilobin, 3,19-Didehydro-12-hydroxysenecionan-11,16-dione, Jacodine

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About This Item

Empirical Formula (Hill Notation):
C18H23NO5
CAS Number:
480-81-9
Molecular Weight:
333.38
UNSPSC Code:
85151701
PubChem Substance ID:
329755594
MDL number:
MFCD00221722

Key Documents

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InChI

1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4-/t14-,15-,18-/m1/s1

SMILES string

C\C=C1\CC(=C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

InChI key

FCEVNJIUIMLVML-QPSVUOIXSA-N

grade

analytical standard

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

−20°C

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Preparation Note

Reconstitution: Dried down, 50 μg/mL after reconstitution with 1 mL of water

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Pyrrolizidine alkaloids from Melampyrum pratense.
E Roeder et al.
Natural toxins, 1(1), 35-37 (1992-01-01)
S R Dueker et al.
Toxicology and applied pharmacology, 117(1), 116-121 (1992-11-01)
Two carboxylesterases (GPL1 and GPH1) were isolated from guinea pig hepatic microsomes and assayed for activity using the following pyrrolizidine alkaloids (PAs): seneciphylline (SNP), monocrotaline (MCT), and a mixture of senecionine (SEN) and integerrimine (INT) referred to as SEN-INT. GPH1
B Kedzierski et al.
Analytical biochemistry, 152(1), 59-65 (1986-01-01)
An improved method utilizing reverse-phase liquid chromatography on a styrene-divinylbenzene column (PRP-1) and ultraviolet detection was developed for the simultaneous determination of the pyrrolizidine alkaloids (PAs) senecionine, seneciphylline, and retrorsine and their major metabolites produced during in vitro transformation of
H S Ramsdell et al.
Toxicology letters, 37(3), 241-249 (1987-08-01)
In vivo pretreatment of rats with phenobarbital or beta-naphthoflavone reduced the specific activity of microsomal pyrrolizidine alkaloid N-oxide formation. Heat pretreatment of microsomes under conditions intended to selectively inactivate the flavin-containing monooxygenase did not lower the rate of N-oxidation. Incubation
S Q Yuan et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 25(3), 191-197 (1990-01-01)
Six alkaloids were isolated from Gynura segetum (Lour.) Merr. Four of them were identified. Alkaloids I and II were identified as known senecionine and seneciphylline, respectively. Alkaloids III and IV were found to be new compounds named seneciphyllinine and (E)-seneciphylline
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