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32328

Supelco

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
MDL number:
MFCD01684783
UNSPSC Code:
85151701
PubChem Substance ID:
329754139
NACRES:
NA.24

grade

analytical standard

Quality Level

100

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

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

InChI key

HJSJELVDQOXCHO-HTQZYQBOSA-N

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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

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

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

Storage Class Code

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
SZBF236XV
SZBE021XV

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T Hartmann et al.
Insect biochemistry and molecular biology, 31(11), 1041-1056 (2001-08-25)
Platyphora boucardi leaf-beetles sequester tertiary pyrrolizidine alkaloids of the lycopsamine type acquired from their host-plant Prestonia portobellensis (Apocynaceae) and synthesize their own alkaloids from exogenous retronecine and aliphatic 2-hydroxy acids. Tracer studies with [14C]rinderine and its N-oxide revealed that P.
Lee Williams et al.
Toxicology and applied pharmacology, 182(2), 98-104 (2002-07-26)
Riddelliine is a representative pyrrolizidine alkaloid, a class of naturally occurring toxic phytochemicals present in plant species worldwide. Human exposure to pyrrolizidine alkaloids occurs through consumption of herbal dietary supplements, including comfrey, and through contaminated livestock products (e.g., milk). A
Alex T Jordan et al.
Archives of insect biochemistry and physiology, 66(4), 183-189 (2007-11-15)
Pyrrolizidine alkaloids (PAs) play a fundamental role in the sexual biology of the salt marsh moth Estigmene acrea. They are precursors for the male courtship pheromone hydroxydanaidal and they stimulate the growth and development of male pheromone-disseminating organs called coremata.
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
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