ChemicalBook > CAS DataBase List > RETRORSINE

RETRORSINE

Product Name: RETRORSINE
CAS No.: 480-54-6
Chemical Name: RETRORSINE
Synonyms: Retrosine;RETRORSIN;RETRORSINE;Retrorcine;β-Longilobine;RETRORSINE(AS);BETA-LONGILOBINE;Retrorsine 100 μg/mL in Water;cis-retronecicacidesterofretronecine;16-dione,12,18-dihydroxy-senecionan-1
CBNumber: CB1256406
Molecular Formula: C18H25NO6
Formula Weight: 351.39
MOL File: 480-54-6.mol

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RETRORSINE Property

Melting point:: 208-211 °C (lit.)
alpha: D18 -17.6° (c = 1.99 in ethanol)
Boiling point:: 485.2°C (rough estimate)
Density: 1.32±0.1 g/cm3 (20 ºC 760 Torr)
refractive index: 1.5100 (estimate)
storage temp.: 2-8°C
solubility: DMSO: Slightly soluble: 0.1-1 mg/mlPBS (pH 7.2): Slightly soluble: 0.1-1 mg/ml
pka: 12.00±0.40(Predicted)
form: Solid
color: White to off-white
Merck: 13,8253
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
InChIKey: BCJMNZRQJAVDLD-VMOBWIEOSA-N
SMILES: N12CC=C3COC(=O)[C@@](O)(CO)[C@H](C)C/C(=C/C)/C(=O)O[C@@]([H])([C@]13[H])CC2
CAS DataBase Reference: 480-54-6
IARC: 3 (Vol. 10, Sup 7) 1987
EPA Substance Registry System: Retrorsine (480-54-6)

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Safety

Hazard Codes: T
Risk Statements: 25
Safety Statements: 22-36/37/39-45
RIDADR: 1544
WGK Germany: 3
RTECS: VH7525000
HazardClass: 6.1(a)
PackingGroup: II
Hazardous Substances Data: 480-54-6(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: R0382
Product name: Retrorsine
Purity: ≥90% (HPLC)
Packaging: 100mg
Price: $268
Updated: 2025/07/31

Sigma-Aldrich

Product number: R0382
Product name: Retrorsine
Purity: ≥90% (HPLC)
Packaging: 500mg
Price: $923
Updated: 2025/07/31

Sigma-Aldrich

Product number: PHL89775
Product name: Retrorsine
Purity: phyproof Reference Substance
Packaging: 10mg
Price: $303
Updated: 2025/07/31

American Custom Chemicals Corporation

Product number: API0009902
Product name: RETRORSINE
Purity: 95.00%
Packaging: 10MG
Price: $573.3
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 48570
Product name: Retrorsine
Packaging: 10mg
Price: $585
Updated: 2021/12/16

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RETRORSINE Chemical Properties,Usage,Production

Uses

Retrorsine-D4 is a labelled analogue of Retrorsine (R279000). Retrorsine is a pyrrolizidine alkaloid that blocks the hepatocyte cell cycle, ultimately affecting hepatocyte proliferative capacity.

Definition

ChEBI: Retrorsine is a macrolide.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. hhtation data reported. When heated to decomposition it emits toxic fumes of NOx.

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^[4].

Animal Model:	Male Wistar rats (180±20 g), portal branch ligation (PBL) model^[4]
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] C.C.J. CULVENOR. Hepato- and pneumotoxicity of pyrrolizidine alkaloids and derivatives in relation to molecular structure[J]. Chemico-Biological Interactions, 1976, 12 3: Pages 299-324. DOI: 10.1016/0009-2797(76)90046-6
[2] M. J. PESTCHANKER O. S G. Pyrrolizidine Alkaloids from Five Senecio Species[J]. Journal of Natural Products , 1986, 49 4: 722-723. DOI: 10.1021/np50046a041
[3] YAN HONG LI. Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model[J]. Journal of ethnopharmacology, 2013, 150 2: Pages 560-567. DOI: 10.1016/j.jep.2013.09.010

RETRORSINE Preparation Products And Raw materials

Raw materials

Preparation Products

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480-54-6, RETRORSINERelated Search:

ALLYL ISOVALERATE 3-METHOXYPYRROLIDINE (2-Propenyloxy)propanol Butyl hydroxyacetate 3-ALLYLOXY-1,2-PROPANEDIOL 2-Dimethylaminoethyl acetate DIMETHYL 2-METHYLADIPATE 3-Butoxypropanamine 2-HYDROXY-3-METHYLBUTYRIC ACID 3-Pyrrolidinol 2-HYDROXY-N-BUTYRIC ACID ETHYL ESTER RETRORSINE Methyl (R)-(+)-lactate ISO-PROPYL ACRYLATE ISOBUTYRIC ACID N-PROPYL ESTER 3-(DIMETHYLAMINO)PROPYL ACRYLATE 1-AMINO-5-HEXENE 2-METHYL-5-HEXEN-2-OL

BETA-LONGILOBINE

12,18-DIHYDROXYSENECIONAN-11,16-DIONE

RETRORSIN

RETRORSINE

16-dione,12,18-dihydroxy-senecionan-1

5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-hydroxymethyl-5-3-ethylidene-4

cis-retronecicacidesterofretronecine

methyl(1,6)dioxacyclododeca(2,3,4-gh)pyrrolizidine-2,7-dione

Retrosine

trans-15-ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-

RETRORSINE(AS)

β-Longilobine, 12,18-Dihydroxysenecionan-11,16-dione

β-Longilobine

Retrorcine

[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)-

Retrorsine 100 μg/mL in Water

480-54-6

C18H23O5N