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JERVINE structure
JERVINE structure

JERVINE

Iupac Name:(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,
11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,
11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,
2-b]pyridine]-11-one
CAS No.: 469-59-0
Molecular Weight:425.60346
Modify Date.: 2022-11-29 12:02
Introduction: 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 View more+
1. Names and Identifiers
1.1 Name
JERVINE
1.2 Synonyms

(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-tetramethylspiro[9H-benzo[a]fluorene-9,2′(3′H)-furo[3,2-b]pyridin]-11(1H)-one Jervin Jervine(8CI) NSC 23898 NSC 7520 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-,[3S-(3a,6aa,6bb,9a(3'S*,3'aR*,6'R*,7'aS*),11ab,11ba)]- 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)- 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-, [3S-(3α,6aα,6bβ,9α(3′S*,3′aR*,6′R*,7′aS*),11aβ,11bα)]- Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3b,23b)- Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3β,23β)-

1.3 CAS No.
469-59-0
1.4 CID
10098
1.5 EINECS(EC#)
207-417-9
1.6 Molecular Formula
C27H39NO3 (isomer)
1.7 Inchi
InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1
1.8 InChkey
CLEXYFLHGFJONT-DNMILWOZSA-N
1.9 Canonical Smiles
CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1
1.10 Isomers Smiles
C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5C(=O)C4=C3C)C)O)C)NC1
2. Properties
2.1 Density
1.18
2.1 Melting point
242- 244°C
2.1 Boiling point
592°Cat760mmHg
2.1 Refractive index
1.59
2.1 Flash Point
311.8°C
2.1 Precise Quality
425.29300
2.1 PSA
58.56000
2.1 logP
4.50970
2.1 Solubility
Insuluble (4.7E-3 g/L) (25 oC),
2.2 Λmax
250nm(lit.)
2.3 Appearance
White to Almost white powder to crystal
2.4 Chemical Properties
White Crystalline Solid
2.5 Color/Form
NEEDLES FROM METHANOL + WATER
2.6 Decomposition
When heated to decomp ... emits toxic fumes of /nitrogen oxides/.
2.7 pKa
14.98±0.70(Predicted)
2.8 Water Solubility
SOL IN ALCOHOL, ACETONE, CHLOROFORM
2.9 Spectral Properties
SPECIFIC OPTICAL ROTATION (ETHANOL): -150 DEG @ 20 DEG C/D; -167.6 DEG @ 20 DEG C/D (CHLOROFORM); MAX ABSORPTION: 250, 360 NM (E= 15,000, 60)
IR: 21767 (Sadtler Research Laboratories IR Grating Collection)
UV: 3-1008 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
2.10 Stability
Store in Freezer at - 20°C
2.11 StorageTemp
−20°C
3. Use and Manufacturing
3.1 Methods of Manufacturing
TOTAL SYNTHESIS: KUTNEY ET AL, CAN J CHEM 53, 1796 (1975).
3.2 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 JERVINESupplier
3.3 Usage
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
4. Safety and Handling
4.1 Symbol
GHS06;
4.1 Hazard Codes
Xn
4.1 Signal Word
DANGER
4.1 Risk Statements
R22
4.1 Safety Statements
Poison by ingestion, intravenous, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. A natural toxin found in some plants. When heated to decomposition it emits toxic fumes of NOx.
4.1 Packing Group
III
4.1 Hazard Class
6.1
4.1 Hazard Declaration
H301
4.1 RIDADR
UN 2811 6.1/PG 3
4.1 Caution Statement
P301 + P310
4.1 WGK Germany
3
4.1 RTECS
WG9700000
4.1 Safety

Poison by ingestion, intravenous, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. A natural toxin found in some plants. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:  Xn Harmful
Risk Statements:  22 
R22:Harmful if swallowed.
RIDADR:  UN 2811 6.1/PG 3
WGK Germany:  3
RTECS:  WG9700000

4.2 Specification

1.Removal in wastewater treatment of Jervine (CAS NO.469-59-0):
Total removal:23.33  percent
Total biodegradation:0.27  percent
Total sludge adsorption:23.06  percent
Total to air:0.00  percent
(using 10000 hr Bio P,A,S)
2.Physiological effects
 Jervine (CAS NO.469-59-0) is a potent teratogen causing birth defects in vertebrates. In severe cases it can cause cyclopia and holoprosencephaly. Similar to cyclopamine, which also occurs in the veratrum genus, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation.
3.Mechanism of action
 The biological activity of  Jervine (CAS NO.469-59-0) is mediated via its interaction with the 7 pass trans membrane protein smoothened. Jervine binds with and inhibits smoothened, when smoothened inhibited, the GLI1 trancription cannot be activated and hedgehog target genes cannot be transcribed.

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

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Storage Conditions
TOTAL SYNTHESIS: KUTNEY ET AL, CAN J CHEM 53, 1796 (1975).
9.1 Natural Pollution Sources
STEROIDAL ALKALOID FOUND IN VERATRUM GRANDIFLORUM (MAXIM) LOES F, V ALBUM L, V VIRIDE SOL, LILIACEAE: SAITO BULL CHEM SOC JAPAN 9, 15 (1934), CA 28, 2463 (1934); POETHKE, ARCH PHARM 275, 357, 571 (1937); 276, 170 (1938); 282, 56 (1944); SEIFERLE ET AL, J ECON ENTOMOL 35, 35 (1942); JACOBS, CRAIG, J BIOL CHEM 160, 555 (1945).
9.2 Metabolism
Malformations in hatched chicks were produced by direct application of 1-2 mg of cyclopamine to the embryonic shield of windowed chicken eggs. This showed that maternal metabolic alteration of cyclopamine was not necessary. /PRC: Cyclopamine is a member of the jerveratum group as is jervine/. /CYCLOPAMINE/|INCORPORATION OF ACETATE-1-(14)C, CHOLESTEROL-4-(14)C, & OF CHOLESTEROL-26-(14)C INTO JERVINE & VERATRAMINE GAVE A LABELING PATTERN CONSISTENT WITH THE HYPOTHESIS THAT A KEY INTERMEDIATE DERIVED FROM EPIRUBIJERVINE WAS CONVERTED INTO THE C-NOR-D-HOMOSTEROIDAL ALKALOIDS (JERVINE & VERATRAMINE) BY SEPARATE PATHWAYS IN VERATRUM GRANDIFLORUM.
9.3 Human Toxicity Excerpts
Several species of the Veratrum genus are associated with toxicity in humans and animals. The principal toxins are steroid alkaloids; some have a modified steroid template, whereas others differ in their esterified acid moieties. These alkaloids act by increasing the permeability of the sodium channels of nerve cells, causing them to fire continuously. Increased stimulation, associated with the vagal nerve results in a reflex that causes the triad of responses known as the Bezold-Jarisch reflex: hypotension, bradycardia and apnea. Clinically, various Veratrum extracts were marketed for use as antihypertensive drugs, but because of their narrow therapeutic index were withdrawn from the market. Following the ingestion of Veratrum alkaloids, expected signs and symptoms include vomiting and abdominal pain, followed by cardiovascular effects such as bradycardia, hypotension and cardiac conduction abnormalities and death. Similar symptoms arise in other mammalian species ingesting these alkaloids; teratogenic effects may occur to the fetuses of animals that have grazed on Veratrum californicum. Treatment consists of supportive care, with an emphasis on hemodynamic stability with fluid replacement, atropine and vasopressors. The onset of symptoms occurs between 30 minutes and 4 hours, and the duration of the illness can range from 1 to 10 days; however, with prompt supportive care, patients typically make a full recovery within 24 hours.
9.4 Mesh Entry Terms
jervine
9.5 Manufacturing Info
An alkamine isolated from Veratrum album.
10. Computational chemical data
  • Molecular Weight: 425.60346g/mol
  • Molecular Formula: C27H39NO3
  • Compound Is Canonicalized: True
  • XLogP3-AA: 2.9
  • Exact Mass: 425.29299411
  • Monoisotopic Mass: 425.29299411
  • Complexity: 876
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 58.6
  • Heavy Atom Count: 31
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB6MAAAAAAAAAAAAAAAAAAAAaIAAAA8QIEAAAAAAFiAAAAAHgAQCAAAD3zhgAYCAALABgCIAqBSAAAAAAAgAAAACIEIAEgCFBIAoQAHUAAG0ACYIQO4yPCPgAAAAAAAAABAAAAAAAAAAQAACAAAAA==
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