| Identification | Back Directory | [Name]
JERVINE | [CAS]
469-59-0 | [Synonyms]
Iervin
jerwiny
JERVINE
Jervin-11-one
11-KETOCYCLOPAMINE
DL-ISOLEUCINE GRADE II
17,23β-Epoxy-3β-hydroxyveratraman-11-one
(323-17,23-Epoxy-3-hydroxyveratraman-11-one
(3BETA, 23BETA)-17,23-EPOXY-3-HYDROXYVERATRAMAN-11-ONE
17,23-epoxy-3-hydroxy-,(3beta,23beta)-veratraman-11-on
17,23-epoxy-3-hydroxy-,(3-beta,23-beta)-veratraman-11-on
Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3beta,23beta)-
(3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one, 11-Ketocyclopamine
spiro(9h-benzo(a)fluorene-9,2’(3’h)-furo(3,2-b)-pyridin)-11(1h)-one,2,3,3’a,4,
4’,5’,6,6’,6a,6b,7,7’,7’a,8,11a,11b-hexadecahydro-3-hydroxy-3’,6’,10,11b-tetra
Spiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)-pyridin)-11(1H)-one,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b-hexadecahydro-3-hydroxy-3',6',10,11b-tetramethyl-
(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b-hexadecahydro-3-hydroxy-3',6',10,11b-tetramethyl-Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-11(1H)-one
Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-11(1H)-one,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b-hexadecahydro-3-hydroxy-3',6',10,11b-tetraMethyl-,(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)- | [EINECS(EC#)]
207-417-9 | [Molecular Formula]
C27H39NO3 | [MDL Number]
MFCD01684066 | [MOL File]
469-59-0.mol | [Molecular Weight]
425.6 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [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 |
| Hazard Information | Back Directory | [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 | [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]28D + 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]26D - 82° (EtOH).
On further hydrogenation, the tetrahydro compound is formed, m.p. 216-
221°C; [α]28D - 18° (EtOH). Jervine may be reduced by sodium in butanol to
a:-dihydrojervinol, m.p. 223-5°C; [α]27D - 107° (EtOH). The similar reduction
of dihydrojervine yields (3-dihydrojervino1, m.p. 286-9°C; [α]28D-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 | [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) |
| Safety Data | Back Directory | [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) |
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