Jervine

Base Information

• Chemical Name: Jervine
• CAS No.: 469-59-0
• Molecular Formula: C27H39 N O3
• Molecular Weight: 425.612
• Hs Code.: 29349990
• European Community (EC) Number: 207-417-9
• NSC Number: 23898,7520
• UNII: 19V3ECX465
• DSSTox Substance ID: DTXSID70895026
• Nikkaji Number: J5.926I
• Wikipedia: Jervine
• Wikidata: Q3278036
• Pharos Ligand ID: LYYY4U6K8PLD
• ChEMBL ID: CHEMBL186779
• Mol file: 469-59-0.mol

Synonyms:jervine;jervine, acetate, (3beta,23beta)-isomer

Chemical Property of Jervine

Chemical Property:

• Vapor Pressure: 1.75E-16mmHg at 25°C
• Melting Point: 242- 244°C
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 592°Cat760mmHg
• PKA: 14.98±0.70(Predicted)
• Flash Point: 311.8°C
• PSA: 58.56000
• Density: 1.18g/cm³
• LogP: 4.50970
• Storage Temp.: −20°C
• Solubility.: methanol: >2 mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 425.29299411
• Heavy Atom Count: 31
• Complexity: 876

Purity/Quality:

98% ^*data from raw suppliers

Jervine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1
• Isomeric 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
• 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
• 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

Technology Process of Jervine

There total 14 articles about Jervine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(23R)-17,23-epoxy-(5α,13βH)-veratrane-3β,13-diol (17008-94-5) → jervine (469-59-0)

Guidance literature:

Multi-step reaction with 10 steps

1: (acetylation)

2: SOCl₂, Py

3: CrO₃ / pyridine

4: (hydrolysis)

5: CrO₃ / dimethylformamide

6: DDQ

7: H₂ / Pd

8: (acetylation)

9: NaBH₄

10: KOH / dimethylsulfoxide

With pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; thionyl chloride; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In pyridine; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja00993a048

Reference yield:

(23R)-28-acetyl-17,23-epoxy-3β-hydroxy-(5α)-veratr-12-en-11-one (17008-98-9) → jervine (469-59-0)

Guidance literature:

Multi-step reaction with 6 steps

1: CrO₃ / dimethylformamide

2: DDQ

3: H₂ / Pd

4: (acetylation)

5: NaBH₄

6: KOH / dimethylsulfoxide

With chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja00993a048

Reference yield:

(23R)-28-acetyl-17,23-epoxy-(5α)-veratr-12-ene-3,11-dione (14705-69-2) → jervine (469-59-0)

Guidance literature:

Multi-step reaction with 5 steps

1: DDQ

2: H₂ / Pd

3: (acetylation)

4: NaBH₄

5: KOH / dimethylsulfoxide

With potassium hydroxide; sodium tetrahydroborate; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In dimethyl sulfoxide;

DOI:10.1021/ja00993a048

upstream raw materials:

N-acetyljervine

O-acetyljervine

(23R)-17,23-epoxy-(5α,13βH)-veratrane-3β,13-diol

(23R)-28-acetyl-17,23-epoxy-3β-hydroxy-(5α)-veratr-12-en-11-one

Downstream raw materials:

N-acetyljervine

N,O-Diacetyl-jervin

O-acetyljervine

(23R)-17,23-epoxy-3β-hydroxy-28-methyl-veratra-5,12-dien-11-one

Refernces

• 1、 Spragne et al.. "". . p. 4857. Retrieved 1971.