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JERVINE

CAS No.
469-59-0
Chemical Name:
JERVINE
Synonyms
Iervin;jerwiny;JERVINE;23ßJervine>Jervine-RM;Jervin-11-one;Jervine (8CI);Jervine ((3ß11-KETOCYCLOPAMINE
CBNumber:
CB7326145
Molecular Formula:
C27H39NO3
Molecular Weight:
425.6
MDL Number:
MFCD01684066
MOL File:
469-59-0.mol
Last updated:2024-11-19 20:33:22

JERVINE Properties

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
FDA UNII 19V3ECX465

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H360D
Precautionary statements  P201-P301+P310+P330
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)
NFPA 704
0
2 0

JERVINE price More Price(44)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich J4145 Jervine ≥98% (HPLC), powder 469-59-0 1mg $197 2024-03-01 Buy
Sigma-Aldrich 420210 Jervine 469-59-0 1mg $181 2023-01-07 Buy
TCI Chemical J0009 Jervine >97.0%(HPLC) 469-59-0 10mg $317 2024-03-01 Buy
Cayman Chemical 11723 Jervine ≥98% 469-59-0 1mg $32 2024-03-01 Buy
Cayman Chemical 11723 Jervine ≥98% 469-59-0 5mg $100 2024-03-01 Buy
Product number Packaging Price Buy
J4145 1mg $197 Buy
420210 1mg $181 Buy
J0009 10mg $317 Buy
11723 1mg $32 Buy
11723 5mg $100 Buy

JERVINE Chemical Properties,Uses,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

Global( 196)Suppliers
Supplier Tel Email Country ProdList Advantage
Shanghai Zheyan Biotech Co., Ltd.
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Chengdu GLP biotechnology Co Ltd
028-87075086 13350802083 scglp@glp-china.com CHINA 1824 58
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897 sales@biopurify.com China 3772 58
Hubei Jusheng Technology Co.,Ltd.
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NanJing Spring & Autumn Biological Engineering CO., LTD.
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BOC Sciences
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Shanghai Standard Technology Co., Ltd.
18502101150 ft-sales@nature-standard.com CHINA 1923 58
Neostar United (Changzhou) Industrial Co., Ltd.
+86-0519-85551759 +8613506123987 marketing1@neostarunited.com China 8838 58

View Lastest Price from JERVINE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Jervine pictures 2024-11-19 Jervine
469-59-0
US $64.00-273.00 / mg 99.86% 10g TargetMol Chemicals Inc.
Jervine pictures 2023-02-24 Jervine
469-59-0
US $0.00 / mg 20mg ≥98%(HPLC) 100 g Shanghai Standard Technology Co., Ltd.
factory price Jervine 469-59-0 pictures 2022-02-14 factory price Jervine 469-59-0
469-59-0
US $186.00 / g 10mg ≥98% 1000.00 kgs NanJing Spring & Autumn Biological Engineering CO., LTD.
  • Jervine pictures
  • Jervine
    469-59-0
  • US $64.00-273.00 / mg
  • 99.86%
  • TargetMol Chemicals Inc.
  • Jervine pictures
  • Jervine
    469-59-0
  • US $0.00 / mg
  • ≥98%(HPLC)
  • Shanghai Standard Technology Co., Ltd.
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 (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 Jervine> factory price Jervine 469-59-0 Jervine - CAS 469-59-0 - Calbiochem Jervine ((3ß 23ß Jervine(11-Ketocyclopamine) Jervine, 98%, from Veratrum nigrum L. Jervine (8CI) (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 Jervine in methanol Jervine-RM Glycerol Impurity 17 Disodium Salt(Glycerophosphoric acid Disodium Salt) 469-59-0 460-59-0 reagent standard substance Intermediates & Fine Chemicals Pharmaceuticals Steroids Lipid signaling