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Merck
CN

32328

Retronecine

analytical standard

Synonym(s):

(1R,7aR)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol

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About This Item

Empirical Formula (Hill Notation):
C8H13NO2
CAS Number:
480-85-3
Molecular Weight:
155.19
NACRES:
NA.24
PubChem Substance ID:
329754139
UNSPSC Code:
85151701
MDL number:
MFCD01684783

Key Documents

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InChI key

HJSJELVDQOXCHO-HTQZYQBOSA-N

SMILES string

[H][C@@]1([C@H](O)CC2)N2CC=C1CO

InChI

1S/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s1

grade

analytical standard

shelf life

limited shelf life, expiry date on the label

storage condition

under inert gas

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

format

neat

storage temp.

2-8°C

Quality Level

100

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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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB7339
BCBT6419

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L H Zalkow et al.
Journal of medicinal chemistry, 31(8), 1520-1526 (1988-08-01)
The C-9 and C-7 monoesters and C-7, C-9 diesters of heliotridine with (S)-(+) and (R)-(-)-2-hydroxy-2-phenylbutyric acid were prepared, converted into their N-oxides, and compared with the corresponding C-9 monoesters of retronecine in the in vivo P388 lymphocytic leukemia screen. Relative
John A Edgar et al.
Journal of chemical ecology, 33(12), 2266-2280 (2007-11-22)
Many pyrrolizidine alkaloid (PA)-adapted insects convert PAs sequestered from their larval host plants into "insect-PAs" in which the acid components of the alkaloids are replaced by small, branched aliphatic 2-hydroxy acids of insect origin. It has been proposed that insect-PAs
Steven M Colegate et al.
Phytochemical analysis : PCA, 24(3), 201-212 (2012-10-17)
A livestock poisoning outbreak near Kingman, Arizona, USA, potentially linked to dehydropyrrolizidine alkaloids, prompted an evaluation of some local plants for the presence of these hepatotoxic alkaloids. To qualitatively and quantitatively examine two species of Cryptantha, a Boraginaceous genus previously
Fang Zhang et al.
Analytica chimica acta, 605(1), 94-101 (2007-11-21)
Pyrrolizidine alkaloids (PAs) are alkaloids which typically contain a necine (7-hydroxy-1-hydroxymethyl-6,7-dihydro-5H-pyrrolizidine) base unit, and they can be found in one third of the higher plants around the world. They are hepatotoxic, mutagenic and carcinogenic and pose a threat to human
Yi-Cheng Yang et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49(11), 2793-2799 (2011-08-17)
Monocrotaline (MCT) is a naturally occurring hepatotoxic pyrrolizidine alkaloid found in plants. This investigation is aimed at furthering the understanding of the role of blood in mediating the transport of MCT and its reactive metabolites in humans. Reactions of monocrotaline
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