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Merck
CN

R0382

倒千里光碱

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

别名:

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

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关于此项目

经验公式(希尔记法):
C18H25NO6
化学文摘社编号:
分子量:
351.39
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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产品名称

倒千里光碱, ≥90% (HPLC)

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

assay

≥90% (HPLC)

mp

208-211 °C (lit.)

Quality Level

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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

Skull and crossbones

signalword

Danger

Hazard Classifications

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

存储类别

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

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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
Norihisa Ichinohe et al.
Cell transplantation, 21(1), 11-22 (2011-06-15)
Cell-based therapies as an alternative to liver transplantation have been anticipated for the treatment of potentially fatal liver diseases. Not only mature hepatocytes (MHs) but also hepatic stem/progenitor cells are considered as candidate cell sources. However, whether the stem/progenitor cells
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
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
Chun-Hsien Yu et al.
Cell transplantation, 18(10), 1081-1092 (2009-08-05)
Efficient repopulation by transplanted hepatocytes in the severely injured liver is essential for their clinical application in the treatment of acute hepatic failure. We studied here whether and how the transplanted hepatocytes are able to efficiently repopulate the toxin-induced acute

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