JERVINE Struktur

Jervin

Bezeichnung:Jervin

CAS-Nr469-59-0

Englisch Name:JERVINE

CBNumberCB7326145

SummenformelC27H39NO3

Molgewicht425.6

MOL-Datei469-59-0.mol

Synonyma

Jervin

Jervin physikalisch-chemischer Eigenschaften

Schmelzpunkt	242- 244°C
alpha	D20 -150° (ethanol) (Saito); D20 -167.6° (chloroform) (Poethke)
Siedepunkt	541.31°C (rough estimate)
Dichte	1.18±0.1 g/cm3 (20 ºC 760 Torr)
Brechungsindex	1.6400 (estimate)
storage temp.	−20°C
Löslichkeit	methanol: >2 mg/mL
Aggregatzustand	solid
pka	14.98±0.70(Predicted)
Farbe	White
maximale Wellenlänge (λmax)	250nm(lit.)
Merck	14,5264
Stabilität	Store in Freezer at - 20°C

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	WG9700000
HazardClass	6.1
PackingGroup	III
HS Code	29349990
Giftige Stoffe Daten	469-59-0(Hazardous Substances Data)
Toxizität	LD50 i.v. in mice: 9.3 mg/kg (Krayer); LD50 s.c. in male mice: 29 mg/kg (Tanaka)

Gefahreninformationscode (GHS)

JERVINE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
Beschreibung
First obtained from Veratrum grandiflorum by Wright and Luff, this alkaloid is also present in V. album. It was originally given the formula C26H3703N. 2H20, subsequently altered to that given above by Jacobs and Craig. The base crystallizes from aqueous EtOH in stellate groups of colourless prisms and has [α]_D - 147° (EtOH). The hydrochloride (dihydrate) has m.p. 208°C (Wright and Luff) or 330-334°C (dec.) according to Jacobs and Craig, the latter finding a change in crystalline form at 280°C. The hydriodide has m.p. 302-5°C; the nitrate and aurichloride are both crystalline and the picrate melts at 278-284°C. TheN-nitroso derivative has m.p. 246-7°C; the N-acety1 compound, m.p. 161-2°C and the O,N-diacetyl derivative, m.p. 17 6-7°C.
Treatment with aluminium tert-butoxide gives Δ4-jervone, m.p. 193-4°C; [α]²⁸_D + 28.3° (EtOH), giving an oxime, m.p. 287-9°C and reduced by aluminium isopropoxide to Δ4-jervine, m.p. 203- 2 11°C. Catalytic hydrogenation with Pd-C yields the dihydro derivative, m.p. 248-251°C; [α]²⁶_D - 82° (EtOH). On further hydrogenation, the tetrahydro compound is formed, m.p. 216- 221°C; [α]²⁸_D - 18° (EtOH). Jervine may be reduced by sodium in butanol to a:-dihydrojervinol, m.p. 223-5°C; [α]²⁷_D - 107° (EtOH). The similar reduction of dihydrojervine yields (3-dihydrojervino1, m.p. 286-9°C; [α]²⁸_D-4 C(EtOH). On Se dehydrogenation, the alkaloid behaves like cevine (q.v.) giving a mixture of bases and hydrocarbons from which the following have been isolated; 5-methyl- 2-ethylpyridine; 5-methyl-2-ethyl-3-hydroxypyridine; C2oH22 , m.p. 79°C; C24H30, m.p. 100- 1°C; C2l H24 , m.p. 70-8 1°C; C2oH 16 , m.p. I 25-7°C and C22H20 , m.p. I 54-5℃。
In large doses, the alkaloid produces vasodilatation and a fall in blood pressure
Chemische Eigenschaften
White Crystalline Solid
Verwenden
Has antibacterial properties. Jervine demonstrates teratogenic properties. It is the starting material for C-nor-D-homosteroids. Jervine induces holoprosencephaly and blocks endogenous Sonic hedgehog signaling
Definition
ChEBI: Jervine is a member of piperidines.
Lager
-20°C
läuterung methode
4 Crystallise Jervine from MeOH/H2O or Me2O. The hydrochloride has m 300-302o (from MeOH/Et2O), and the picrate has m 26
Einzelnachweise
Wright, Luff., J. Chern. Soc., 35,405 (1879)
Saltzberger., Arch. Pharrn., 228,462 (1890)
Bredemann., Apoth. Zeit., 21,41,53 (1906)
Saito, Suginome, Takaoka., Bull. Chern. Soc. Japan, 9, 15(1934)
Saito, Suginome, Takaoka., ibid, 11, 168, 172 (I936)
Poethke., Arch. Pharrn., 357,571 (I937)
Poethke., ibid, 276, 170 (1938)
Jacobs, Craig., J. BioI. Chern., 148, 51 (1943)
Seiferle.,J. Econ. Entorn., 35,35 (1942)
Jacobs et al., J. Bioi. Chern., 170, 635 (1947)
Wintersteiner et al., J. A mer. Chern. Soc., 73, 2970 (1951)
Wintersteiner, Hosansky., ibid, 74,4474 (1952)
Stereochemistry:
Kupchan, Suffness., J. A mer. Chern. Soc., 90, 2730 (1968)
Masamune et al., Tetrahedron, 24, 3461 (1968)

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