Vincaminol

Vincaminol (C20H26N2O2) is a chemical that is a part of the Vinca alkaloid group, which were discovered in the 1950s by a Canadian scientist and are derived from Vinca minor (periwinkle).[1][2] Vincaminol is not as well known as some of the other Vinca alkaloids such as vinblastine, vinorelbine, vincristine, and vindesine, which are the four main, medically useful Vinca alkaloids.

Vincaminol
Names
IUPAC name
14α-(Hydroxymethyl)-14,15-dihydro-3α,16α-eburnamenin-14β-ol
Systematic IUPAC name
(41S,12S,13aS)-13a-Ethyl-12-(hydroxymethyl)-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C20H26N2O2/c1-2-19-9-5-10-21-11-8-15-14-6-3-4-7-16(14)22(17(15)18(19)21)20(24,12-19)13-23/h3-4,6-7,18,23-24H,2,5,8-13H2,1H3/t18-,19+,20+/m1/s1
    Key: YCXHPBHFOLIYEB-AABGKKOBSA-N
  • InChI=1/C20H26N2O2/c1-2-19-9-5-10-21-11-8-15-14-6-3-4-7-16(14)22(17(15)18(19)21)20(24,12-19)13-23/h3-4,6-7,18,23-24H,2,5,8-13H2,1H3/t18-,19+,20+/m1/s1
    Key: YCXHPBHFOLIYEB-AABGKKOBBO
  • CC[C@@]12CCCN3[C@@H]1c4c(c5ccccc5n4[C@](C2)(CO)O)CC3
Properties
C20H26N2O2
Molar mass 326.440 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses

Vincaminol is used in to synthesize vincamine.

References
  1. PubChem. "Vincaminol". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-15.
  2. Smeyers, Yves G.; Smeyers, Nadine J.; Randez, Juan J.; Hernandez-Laguna, A.; Galvez-Ruano, E. (1991-06-01). "A structural and pharmacological study of alkaloids of Vinca Minor". Molecular Engineering. 1 (2): 153–160. doi:10.1007/BF00420051. ISSN 1572-8951.


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