CAS Number480-54-6
Synonyms(15Z)-12,18-Dihydroxysenecionan-11,16-dione; isatidine; trans-15-Ethylidene-12b-hydroxy-12a-hydroxymethyl-13b-methylsenec-1-enine; b-Longilobine; 12,18-dihydroxy-senecionane-11,16-dione; 12,18-Dihydroxysenecionan-11,16-dione; β-Longilobine; cis-Retronecic acid ester of retronecine; Retrorsin; MFCD00013331
Molecular FormulaC18H25NO6
Molecular Weight351.39
Purity90%
Density1.3±0.1 g/cm3
Boiling Point583.2±50.0 °C at 760 mmHg
Melting Point208-211ºC(lit.)
AppearanceWhite to off-white solid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 480-54-6 |
| Catalog No. | 2A-0202095 |
| Chinese Name | 倒千里光碱 |
| Synonyms | (15Z)-12,18-Dihydroxysenecionan-11,16-dione; isatidine; trans-15-Ethylidene-12b-hydroxy-12a-hydroxymethyl-13b-methylsenec-1-enine; b-Longilobine; 12,18-dihydroxy-senecionane-11,16-dione; 12,18-Dihydroxysenecionan-11,16-dione; β-Longilobine; cis-Retronecic acid ester of retronecine; Retrorsin; MFCD00013331 |
| Molecular Formula | C18H25NO6 |
| Molecular Weight | 351.39 |
| Purity | 90 |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 583.2±50.0 °C at 760 mmHg |
| Melting Point | 208-211ºC(lit.) |
| Appearance | White to off-white solid |
| Storage Condition | Room temperature, sealed, protected from light, ve |
| Packaging | II |
| Application | Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind to DNA and inhibit the proliferation of liver cells. |
| PubChem ID | 12550 |
| SMILES | CC=C1CC(C)C(O)(CO)C(=O)OCC2=CCN3CCC(OC1=O)C23 |
| InChI | 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 |
| Hazard Symbols | 6.1(a) |
| Bioactivity | Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes[1][2]. Related Catalog Research Areas >> Others Signaling Pathways >> Others >> Others In Vitro Retrorsine (60-240 μM; 24 hours) significantly reduces HSEC-CYP3A4 cells viability, depletes GSH, and increases formation of pyrrole-protein adducts[3]. Cell Viability Assay[3] Cell Line: HSEC-CYP3A4 cells Concentration: 60 μM, 120 μM , 240 μM Incubation Time: 24 hours Result: Significantly decreased cell viability. In Vivo Retrorsine (30 mg/kg; i.p.; twice) impairs liver regeneration in the PBL model not only by an S or G2/M phase block, but also by a block located before the G1/S transition of the cell cycle[1]. Animal Model: Male Wistar rats (180±20 g), portal branch ligation (PBL) model[1] Dosage: 30 mg/kg Administration: Intraperitoneal injection, twice, separated by 2-week interval Result: Strongly impaired the liver weight gain, protein and DNA synthesis as well as induction of cell cycle related proteins in the regenerating lobes after PBL. References [1]. F J Cubero, et al. Hepatic proliferation in Gunn rats transplanted with hepatocytes: effect of retrorsine and tri-iodothyronine. Cell Prolif. 2005 Jun;38(3):137-46. [2]. F J Cubero, et al. Hepatic proliferation in Gunn rats transplanted with hepatocytes: effect of retrorsine and tri-iodothyronine. Cell Prolif. 2005 Jun;38(3):137-46. [3]. Yao Lu, et al. Establishment of a novel CYP3A4-transduced human hepatic sinusoidal endothelial cell model and its application in screening hepatotoxicity of pyrrolizidine alkaloids. J Environ Sci Health C Toxicol Carcinog. 2020;38(2):169-185. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 583.2±50.0 °C at 760 mmHg Melting Point 208-211ºC(lit.) Molecular Formula C18H25NO6 Molecular Weight 351.394 Flash Point 306.5±30.1 °C Exact Mass 351.168182 PSA 96.30000 LogP -0.14 Vapour Pressure 0.0±3.7 mmHg at 25°C Index of Refraction 1.590 InChIKey BCJMNZRQJAVDLD-CQRYIUNCSA-N SMILES CC=C1CC(C)C(O)(CO)C(=O)OCC2=CCN3CCC(OC1=O)C23 |
| Use of | Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes[1][2]. Properties Articles28 Name retrorsine Synonym More Synonyms isatidine Biological Activity Description Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes[1][2]. Related Catalog Research Areas >> Others Signaling Pathways >> Others >> Others References [1]. F J Cubero, et al. Hepatic proliferation in Gunn rats transplanted with hepatocytes: effect of retrorsine and tri-iodothyronine. Cell Prolif. 2005 Jun;38(3):137-46. [2]. F J Cubero, et al. Hepatic proliferation in Gunn rats transplanted with hepatocytes: effect of retrorsine and tri-iodothyronine. Cell Prolif. 2005 Jun;38(3):137-46. [3]. Yao Lu, et al. Establishment of a novel CYP3A4-transduced human hepatic sinusoidal endothelial cell model and its application in screening hepatotoxicity of pyrrolizidine alkaloids. J Environ Sci Health C Toxicol Carcinog. 2020;38(2):169-185. Chemical & Physical Properties Molecular Formula C18H25NO6 Exact Mass 351.168182 PSA 96.30000 LogP -0.14 Index of Refraction 1.590 InChIKey BCJMNZRQJAVDLD-CQRYIUNCSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Danger Regulations: 1544 International Maritime Transport Danger Regulations: 1544 International Air Transport Danger Regulations: 1544 14.2 United Nations shipping name European Land Transport Dangerous Regulations: ALKALOIDS, SOLID, N.O.S. (Retrorsine) IMDG Code: ALKALOIDS, SOLID, N.O.S. (Retrorsine) International air transport hazard regulations: Alkaloids, solid, n.o.s. (Retrorsine) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Dangerous Regulations for land transport: II International Dangerous Regulations for sea transport: II International Dangerous Regulations for air transport: II 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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