Rosmarinine | CAS#520-65-0 | pyrrolizidine alkaloid

MedKoo Cat#: 461422 | Name: Rosmarinine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rosmarinine is a non-toxic pyrrolizidine alkaloid.

Chemical Structure

Rosmarinine

CAS#520-65-0

Theoretical Analysis

MedKoo Cat#: 461422

Name: Rosmarinine

CAS#: 520-65-0

Chemical Formula: C18H27NO6

Exact Mass: 353.1838

Molecular Weight: 353.41

Elemental Analysis: C, 61.17; H, 7.70; N, 3.96; O, 27.16

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Rosmarinine;

IUPAC/Chemical Name

(4R,5R,9aR,9a1R,14S,14aS,Z)-7-ethylidene-4,14-dihydroxy-4,5-dimethyldodecahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-3,8-dione

InChi Key

YEXVXKIMPBHRQR-VFQWDWSUSA-N

InChi Code

InChI=1S/C18H27NO6/c1-4-11-7-10(2)18(3,23)17(22)24-9-12-13(20)8-19-6-5-14(15(12)19)25-16(11)21/h4,10,12-15,20,23H,5-9H2,1-3H3/b11-4-/t10-,12+,13-,14-,15-,18-/m1/s1

SMILES Code

[H][C@@]12[C@]([H])(OC(/C(C[C@H]([C@]3(O)C)C)=C\C)=O)CCN1C[C@@H](O)[C@]2([H])COC3=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 353.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Castells E, Mulder PP, Pérez-Trujillo M. Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): implications for toxicity. Phytochemistry. 2014 Dec;108:137-46. doi: 10.1016/j.phytochem.2014.09.006. Epub 2014 Sep 27. PubMed PMID: 25269662. 2: Nieto-Alvarez DA, Calderón JS, Mancilla T. Synthesis of (1R,2R,7R,7aS)-1-hydroxymethyl-2,3,5,6,7,7a-hexahydropyrrolizidine-1,2,7-triol from rosmarinine degradation. Nat Prod Res. 2003 Jan;17(1):33-6. PubMed PMID: 12674140. 3: Styles J, Ashby J, Mattocks AR. Evaluation in vitro of several pyrrolizidine alkaloid carcinogens: observations on the essential pyrrolic nucleus. Carcinogenesis. 1980 Feb;1(2):161-4. PubMed PMID: 22282996. 4: Zündorf I, Wiedenfeld H, Röder E, Dingermann T. Generation and characterization of monoclonal antibodies against the pyrrolizidine alkaloid retrorsine. Planta Med. 1998 Apr;64(3):259-63. PubMed PMID: 9581524.