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MedKoo Cat#: 461251 | Name: Dehydroretrorsine

Description:

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

Dehydroretrorsine is a pyrrolizidine alkaloid metabolite.

Chemical Structure

Dehydroretrorsine
Dehydroretrorsine
CAS#23092-97-9

Theoretical Analysis

MedKoo Cat#: 461251

Name: Dehydroretrorsine

CAS#: 23092-97-9

Chemical Formula: C18H24NO6

Exact Mass: 350.1604

Molecular Weight: 350.39

Elemental Analysis: C, 61.70; H, 6.90; N, 4.00; O, 27.40

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.
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Related CAS #
No Data
Synonym
Dehydroretrorsine; Retrorsine pyrrole;
IUPAC/Chemical Name
(5R,6S,14aR,Z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9a1,13,14,14a-octahydro-9H-12l4-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
InChi Key
HEVMYCOMWSDUCL-UQLKVITLSA-N
InChi Code
1S/C18H23NO6/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/h3-4,6,11,14,20,23H,5,7-10H2,1-2H3/b12-3-/t11-,14-,18-/m1/s1
SMILES Code
O=C(OC1)[C@@](O)(CO)[C@H](C)C/C(C(O[C@@H]2CCn3ccc1C32)=O)=C/C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 350.39 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.

Recalculate based on batch purity %
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: Fashe MM, Juvonen RO, Petsalo A, Rahnasto-Rilla M, Auriola S, Soininen P, Vepsäläinen J, Pasanen M. Identification of a new reactive metabolite of pyrrolizidine alkaloid retrorsine: (3H-pyrrolizin-7-yl)methanol. Chem Res Toxicol. 2014 Nov 17;27(11):1950-7. doi: 10.1021/tx5002964. Epub 2014 Oct 21. PubMed PMID: 25295702. 2: Mattocks AR, Jukes R. Trapping and measurement of short-lived alkylating agents in a recirculating flow system. Chem Biol Interact. 1990;76(1):19-30. PubMed PMID: 2393942. 3: Zhao Y, Xia Q, Yin JJ, Lin G, Fu PP. Photoirradiation of dehydropyrrolizidine alkaloids--formation of reactive oxygen species and induction of lipid peroxidation. Toxicol Lett. 2011 Sep 10;205(3):302-9. doi: 10.1016/j.toxlet.2011.06.020. Epub 2011 Jun 22. PubMed PMID: 21723383. 4: Weidner MF, Sigurdsson ST, Hopkins PB. Sequence preferences of DNA interstrand cross-linking agents: dG-to-dG cross-linking at 5'-CG by structurally simplified analogues of mitomycin C. Biochemistry. 1990 Oct 2;29(39):9225-33. PubMed PMID: 2125476.