Dehydroretrorsine

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

MedKoo CAT#: 461251

CAS#: 23092-97-9

Description: Dehydroretrorsine is a pyrrolizidine alkaloid metabolite.

Chemical Structure

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Dehydroretrorsine
CAS# 23092-97-9
Instruction

Theoretical Analysis

MedKoo Cat#: 461251
Name: Dehydroretrorsine
CAS#: 23092-97-9
Chemical Formula: C18H24NO6
Exact Mass: 350.16
Molecular Weight: 350.390
Elemental Analysis: C, 61.70; H, 6.90; N, 4.00; O, 27.40

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.