Retronecine

Names

[ CAS No. ]:
480-85-3

[ Name ]:
Retronecine

[Synonym ]:
(1R,7aR)-7-hydroxymethyl-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol
Hopeaphenol
(1R-trans)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol
Retronecine
(1R,6S,7R,11bR)-1-(3,4-dihydroxyphenyl)-1,6,7,11b-tetrahydro-6-[(1R,6S,7R,11bR)-1,6,7,11b-tetrahydro-4,8,10-trihydroxy-1,7-bis(4-hydroxyphenyl)benzo[6,7]cyclohepta[1,2,3-cd]benzofuran-6-yl]-7-(4-hydroxyphenyl)benzo[6,7]cyclohepta[1,2,3-cd]benzofuran-4,8,10-triol
(7aR)-7-Hydroxymethyl-(7ar)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1t-ol

Biological Activity

[Description]:

Retronecine ((+)-Retronecine) is a pyrrolizidine alkaloid found in a variety of plants. Retronecine is the most common central core for other pyrrolizidine alkaloids[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Joshua C. Smith, et al. Studies Towards the Total Synthesis of (+)- Retronecine and Anthracimycin. September 2016.

Chemical & Physical Properties

[ Density]:
1.29g/cm3

[ Boiling Point ]:
291.3ºC at 760mmHg

[ Melting Point ]:
119-120°

[ Molecular Formula ]:
C₈H₁₃NO₂

[ Molecular Weight ]:
155.19400

[ Flash Point ]:
161.4ºC

[ Exact Mass ]:
155.09500

[ PSA ]:
43.70000

[ Vapour Pressure ]:
0.000211mmHg at 25°C

[ Index of Refraction ]:
1.611

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
UN 1544

[ RTECS ]:
VH7175000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Articles

Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): implications for toxicity.

Phytochemistry 108 , 137-46, (2014)

Changes in plant chemical defenses after invasion could have consequences on the invaded ecosystems by modifying the interactions between plants and herbivores and facilitating invasion success. Howev...

Transfer of [3H]pyrrolizidine alkaloids from Senecio vulgaris L. and metabolites into rat milk and tissues.

Toxicol. Lett. 17(3-4) , 283-8, (1983)

[3H]Retronecine and [3H]necic acid-labelled senecionine and seneciphylline were prepared biosynthetically with seedlings of Senecio vulgaris L. using [2,3-3H]putrescine and [4,5-3H]isoleucine, respect...

In vivo covalent binding of retronecine-labelled [3H]seneciphylline and [3H]senecionine to DNA of rat liver, lung and kidney.

Chem. Biol. Interact. 54(1) , 57-69, (1985)

Retronecine-labelled [3H]seneciphylline ([3H]SPH) and [3H]senecionine ([3H]SON) of high specific radioactivity (22 and 49 mCi/mmol, respectively) were prepared biosynthetically with seedlings of Senec...