JERVINE Property

Melting point:

242- 244°C

alpha 

D20 -150° (ethanol) (Saito); D20 -167.6° (chloroform) (Poethke)

Boiling point:

541.31°C (rough estimate)

Density 

1.18±0.1 g/cm3 (20 ºC 760 Torr)

refractive index 

1.6400 (estimate)

storage temp. 

−20°C

solubility 

methanol: >2 mg/mL

form 

solid

pka

14.98±0.70(Predicted)

color 

White

λmax

250nm(lit.)

Merck 

14,5264

Stability:

Store in Freezer at - 20°C

Safety

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

WG9700000

HazardClass 

6.1

PackingGroup 

III

HS Code 

29349990

Hazardous Substances Data

469-59-0(Hazardous Substances Data)

Toxicity

LD50 i.v. in mice: 9.3 mg/kg (Krayer); LD50 s.c. in male mice: 29 mg/kg (Tanaka)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P201Obtain special instructions before use.

JERVINE Chemical Properties,Usage,Production

Description

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

Chemical Properties

White Crystalline Solid

Uses

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.

storage

-20°C

Purification Methods

4 Crystallise Jervine from MeOH/H2O or Me2O. The hydrochloride has m 300-302o (from MeOH/Et2O), and the picrate has m 26

References

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)