methyl (2R)-2-((2S,3R,12bS)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizin-2-yl)-3-hydroxypropanoate

HCID 178665437

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Basic information

CAS: 1245-00-7
Standard SMILES: C=C[C@H]1CN2CCc3c([nH]c4ccccc34)[C@@H]2C[C@@H]1[C@H](CO)C(=O)OC
InChIKey: JGKCGXVOATXMRM-UHEFJODHSA-N
Molecular formula: C21H26N2O3
Average molar mass: 354.4 g/mol
Monoisotopic mass: 354.1943427

Overview

methyl (2R)-2-[(2S,3R,12bS)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate has been reported in Rauvolfia afra, Alstonia angustifolia, and Strychnos pungens with data available.

Names & identifiers

Preferred name: methyl (2R)-2-((2S,3R,12bS)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizin-2-yl)-3-hydroxypropanoate
IUPAC: methyl (2R)-2-[(2S,3R,12bS)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate
English name: (16R)-18,19-Didehydro-17-hydroxycorynan-16-carboxylic acid methyl ester
Molecular formula: C21H26N2O3
Molecular weight: 354.44

Names & synonyms

methyl (2R)-2-[(2S,3R,12bS)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoatemethyl (2R)-2-((2S,3R,12bS)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizin-2-yl)-3-hydroxypropanoateRefChem:1089185Sitsirikine1245-00-716R-sitsirikine(16R)-18,19-Didehydro-17-hydroxycorynan-16-carboxylic acid methyl esterMethyl (R)-3-hydroxy-2-((2S,3R,12bS)-3-vinyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)propanoatesitsirikinorb1689980SCHEMBL30730970HY-N1236

Show more names

Methyl (2R)-2-[(2S,12bS)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate(16R)-18,19-Didehydro-17-hydroxy-17,18-secoyohimban-16-carboxylic acid methyl esterIndolo[2,3-a]quinolizine-2-acetic acid, 3-ethenyl-1,2,3,4,6,7,12,12b-octahydro-α-(hydroxymethyl)-, methyl ester, (αR,2S,3R,12bS)-

AKOS040758596FS-7824DA-67614CS-0016637

Database identifiers

CAS: 1245-00-7
PubChem CID: 3050539
Nikkaji: J14.861J

Properties

Computed structural properties

XLogP: 2.4
Topological polar surface area: 65.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 5
Heavy atoms: 26
Formal charge: 0
Complexity: 539

Physicochemical properties

Melting point: 239 · 239-241℃ (Decomposition)
Boiling point: 545.4 · 545.4±50.0 °C(Predicted)
Density: 1.25 · 1.25±0.1 g/cm3(Predicted)
pka: 14.3 · 14.30±0.10(Predicted)

Chemistry & industry

Applications · 2 items

DescriptionOne of the numerous alkaloids isolated from Vinca species, this base occurs in V. rosea L. and forms colourless crystals from MeOH. It is laevorotatory with[α]26D - 58° (MeOH) and when crystallized from Me2CO forms crystals containing solvent of crystallization, m.p. 181°C. The ultraviolet spectrum in MeOH has absorption maxima at 226, 282 and 290 mf.1. The alkaloid contains a primary alcoholic group and an imino group and yields the hemisulphate, m.p. 239- 241°C (dec.); the picrate, m.p. 226-8°C (dec.) and the O-acetate, m.p. 198°C;[α]26D- 26° (MeOH).

UsesSitsirikine is a Vinca alkaloid[1].

Suppliers25 total

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成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

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上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]

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