Labriformidin

• CAT Number: I030419
• CAS Number: 66419-08-7
• Molecular Formula: C29H40O9
• Molecular Weight: 532.63
• Purity: 98%
• Synonyms: Labriformidin
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (1R,3aS,3bR,5aS,6aS,12aS,13aS,13bS,15aR)-3a,10,11a-trihydroxy-9,13a,15a-trimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)icosahydro-1H,11H-cyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxin-11-one
• InChI: InChI=1S/C29H40O9/c1-14-23(31)24(32)29(34)25(36-14)37-20-11-16-4-5-19-18(26(16,2)12-21(20)38-29)6-8-27(3)17(7-9-28(19,27)33)15-10-22(30)35-13-15/h10,14,16-21,23,25,31,33-34H,4-9,11-13H2,1-3H3/t14?,16-,17+,18-,19+,20-,21-,23?,25?,26-,27+,28-,29?/m0/s1
• InChIKey: ZYJTYYKVURRLGF-FUITYXTESA-N
• SMILES: O=C1OCC([C@H]2CC[C@]3(O)[C@]4([H])CC[C@@]5([H])C[C@@]6([H])[C@](OC7(O)C(O6)OC(C)C(O)C7=O)([H])C[C@]5(C)[C@@]4([H])CC[C@]23C)=C1

Labriformidin is an epoxy cardenolide.

Reference

1: Lynch SP, Martin RA. Cardenolide content and thin-layer chromatography profiles of monarch butterflies,danaus plexippus L., and their larval host-plant milkweed,asclepias viridis walt., in northwestern louisiana. J Chem Ecol. 1987 Jan;13(1):47-70. doi: 10.1007/BF01020351. PubMed PMID: 24301359.
2: Malcolm SB, Cockrell BJ, Brower LP. Cardenolide fingerprint of monarch butterflies reared on common milkweed,Asclepias syriaca L. J Chem Ecol. 1989 Mar;15(3):819-53. doi: 10.1007/BF01015180. PubMed PMID: 24271887.
3: Nelson CJ, Seiber JN, Brower LP. Seasonal and intraplant variation of cardenolide content in the California milkweed,Asclepias eriocarpa, and implications for plant defense. J Chem Ecol. 1981 Nov;7(6):981-1010. doi: 10.1007/BF00987622. PubMed PMID: 24420825.
4: Brower LP, Seiber JN, Nelson CJ, Lynch SP, Holland MM. Plant-determined variation in the cardenolide content, thin-layer chromatography profiles, and emetic potency of monarch butterflies,Danaus plexippus L. Reared on milkweed plants in California: 2.Asclepias speciosa. J Chem Ecol. 1984 Apr;10(4):601-39. doi: 10.1007/BF00994224. PubMed PMID: 24318600.
5: Brower LP, Seiber JN, Nelson CJ, Lynch SP, Tuskes PM. Plant-determined variation in the cardenolide content, thin-layer chromatography profiles, and emetic potency of monarch butterflies,Danaus plexippus reared on the milkweed,Asclepias eriocarpa in California. J Chem Ecol. 1982 Mar;8(3):579-633. doi: 10.1007/BF00989631. PubMed PMID: 24415043.