ChemicalBook > CAS DataBase List > JERVINE

JERVINE

Product Name
JERVINE
CAS No.
469-59-0
Chemical Name
JERVINE
Synonyms
Iervin;jerwiny;JERVINE;23ßJervine>Jervin-11-one;Jervine (8CI);Jervine ((3ß11-KETOCYCLOPAMINE;DL-ISOLEUCINE GRADE II
CBNumber
CB7326145
Molecular Formula
C27H39NO3
Formula Weight
425.6
MOL File
469-59-0.mol
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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
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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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P201Obtain special instructions before use.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
J4145
Product name
Jervine
Purity
≥98% (HPLC), powder
Packaging
1mg
Price
$197
Updated
2024/03/01
Sigma-Aldrich
Product number
420210
Product name
Jervine
Packaging
1mg
Price
$181
Updated
2023/01/07
TCI Chemical
Product number
J0009
Product name
Jervine
Purity
>97.0%(HPLC)
Packaging
10mg
Price
$317
Updated
2024/03/01
Cayman Chemical
Product number
11723
Product name
Jervine
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
11723
Product name
Jervine
Purity
≥98%
Packaging
5mg
Price
$100
Updated
2024/03/01
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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]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

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)

JERVINE Preparation Products And Raw materials

Raw materials

Preparation Products

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JERVINE Suppliers

Americas 1 Canada 1 China 156 Europe 1 Germany 2 India 2 Japan 1 Switzerland 1 United Kingdom 6 United States 21 Global 192
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View Lastest Price from JERVINE manufacturers

Shanghai Standard Technology Co., Ltd.
Product
Jervine 469-59-0
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
100 g
Release date
2020-08-13
NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
factory price Jervine 469-59-0 469-59-0
Price
US $186.00/g
Min. Order
10mg
Purity
≥98%
Supply Ability
1000.00 kgs
Release date
2019-06-27
Career Henan Chemical Co
Product
JERVINE 469-59-0
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-23

469-59-0, JERVINERelated Search:

veratramine VERATRIDINE PROTOVERATRINE A Hh-Ag 1.3 LDE-225 Diphosphate N-[3-(1H-Benzimidazol-2-yl)-4-chlorophenyl]-3,4,5-triethoxybenzamide DL-Isoleucine JERVINE(P) JERVINE 2-Isopropyl-5-methyl-2-hexenal 3,7-DIMETHYL-2-METHYLENE-OCT-6-ENAL (Z)-6-HENICOSEN-11-ONE Jervine acetate PSEUDOJERVINE JERVINE(PRIMARY STANDARD) 3-(ALLYLOXY)PIPERIDINE 3-(3-ALLYL)-5-HEXEN-1-AL N-METHYLJERVINE

  • 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)-
  • 17,23-epoxy-3-hydroxy-,(3-beta,23-beta)-veratraman-11-on
  • 17,23-epoxy-3-hydroxy-,(3beta,23beta)-veratraman-11-on
  • 4’,5’,6,6’,6a,6b,7,7’,7’a,8,11a,11b-hexadecahydro-3-hydroxy-3’,6’,10,11b-tetra
  • Iervin
  • Jervine, 98%, from Veratrum nigrum L.
  • Jervine(11-Ketocyclopamine)
  • (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
  • jerwiny
  • 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-
  • spiro(9h-benzo(a)fluorene-9,2’(3’h)-furo(3,2-b)-pyridin)-11(1h)-one,2,3,3’a,4,
  • Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3beta,23beta)-
  • 11-KETOCYCLOPAMINE
  • (3BETA, 23BETA)-17,23-EPOXY-3-HYDROXYVERATRAMAN-11-ONE
  • JERVINE
  • 17,23β-Epoxy-3β-hydroxyveratraman-11-one
  • Jervin-11-one
  • DL-ISOLEUCINE GRADE II
  • (323-17,23-Epoxy-3-hydroxyveratraman-11-one
  • (3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one, 11-Ketocyclopamine
  • 23&szlig
  • Jervine ((3&szlig
  • Jervine - CAS 469-59-0 - Calbiochem
  • factory price Jervine 469-59-0
  • Jervine&gt
  • Jervine (8CI)
  • Glycerol Impurity 17 Disodium Salt(Glycerophosphoric acid Disodium Salt)
  • (2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3-Hydroxy-3',6',10,11b-tetramethyl-1,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11a,11b-hexadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-11(2H)-one
  • (2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3-Hydroxy-3',6',10,11b-tetramethyl-1,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11a,11b-hexadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-11(2H)-one
  • 469-59-0
  • 460-59-0
  • reagent
  • standard substance
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroids
  • Lipid signaling