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R0382

Retrorsine

Name: Retrorsine
Brand: SIGMA

≥90% (HPLC), powder, retronecine-type pyrrolizidine alkaloid

Synonym(s):

Retrorsin, Senecionan-11,16-Dione, 12,18-Dihydroxy- (9CI), β-Longilobine, 12,18-Dihydroxysenecionan-11,16-dione

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₂₅NO₆

CAS Number:

480-54-6

Molecular Weight:

351.39

UNSPSC Code:

12352200

PubChem Substance ID:

24899338

NACRES:

NA.77

Assay:

≥90% (HPLC)

Quality level:

100

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Product Name

Retrorsine, ≥90% (HPLC)

Quality Level

100

assay

≥90% (HPLC)

mp

208-211 °C (lit.)

SMILES string

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

InChI

1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1

InChI key

BCJMNZRQJAVDLD-CQRYIUNCSA-N

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Bioactive Small Molecules

Application

Retrorsine has been used:

as a mito-inhibitory pyrrolizidine alkaloid compound to induce necrotic liver injury in rats
to induce hepatocellular injury in rats
to arrest endogenous hepatocyte growth in mice

Biochem/physiol Actions

Retrorsine (RTS) is a retronecine-type pyrrolizidine alkaloid associated with Senecio and Crotalaria species. It belongs to the pyrrolizidine alkaloid family with mito-inhibitory property and elicits hepatotoxicity. It mediates the inactivation of cytochrome P450 3A4. Retrorsine also inhibits replication of fully differentiated hepatocytes.

pictograms

GHS06

signalword

Danger

hcodes

H300 + H310 + H330

pcodes

P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

涉药品监管产品

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BMP-4 is required for hepatic specification of mouse embryonic stem cell-derived definitive endoderm.

Valerie Gouon-Evans et al.

Nature biotechnology, 24(11), 1402-1411 (2006-11-07)

When differentiated in the presence of activin A in serum-free conditions, mouse embryonic stem cells efficiently generate an endoderm progenitor population defined by the coexpression of either Brachyury, Foxa2 and c-Kit, or c-Kit and Cxcr4. Specification of these progenitors with

Contribution of mature hepatocytes to small hepatocyte-like progenitor cells in retrorsine-exposed rats with chimeric livers.

Ya-Hui Chen et al.

Hepatology (Baltimore, Md.), 57(3), 1215-1224 (2012-10-20)

The potential lineage relationship between hepatic oval cells, small hepatocyte-like progenitor cells (SHPCs), and hepatocytes in liver regeneration is debated. To test whether mature hepatocytes can give rise to SHPCs, rats with dipeptidyl peptidase IV (DPPIV) chimeric livers, which harbored

Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine.

Qingsu Xia et al.

Toxicology letters, 178(2), 77-82 (2008-04-09)

Pyrrolizidine alkaloid-containing plants are widespread in the world and may be the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids require metabolism to exert their genotoxicity and tumorigenicity. Our mechanistic studies have determined that metabolism of the

Direct in vivo cell lineage analysis in the retrorsine and 2AAF models of liver injury after genetic labeling in adult and newborn rats.

Virginie Pichard et al.

PloS one, 4(9), e7267-e7267 (2009-10-01)

When hepatocyte proliferation is impaired, liver regeneration proceeds from the division of non parenchymal hepatocyte progenitors. Oval cells and Small Hepatocyte-like Progenitor Cells (SHPCs) represent the two most studied examples of such epithelial cells with putative stem cell capacity. In

HSQC-1,1-ADEQUATE and HSQC-1,n-ADEQUATE: enhanced methods for establishing adjacent and long-range 13C-13C connectivity networks.

Gary E Martin et al.

Journal of natural products, 74(11), 2400-2407 (2011-11-08)

1H-13C GHSQC and GHMBC spectra are irrefutably among the most valuable 2D NMR experiments for the establishment of unknown chemical structures. However, the indeterminate nature of the length of the long-range coupling(s) observed via the (n)J(CH)-optimized delay of the GHMBC

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Global Trade Item Number

SKU	GTIN
R0382-500MG	04061833631584
R0382-100MG	04061836693824

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