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Lupinin Produkt Beschreibung

(-)-LUPININE Struktur
486-70-4
CAS-Nr.
486-70-4
Bezeichnung:
Lupinin
Englisch Name:
(-)-LUPININE
Synonyma:
LUPININ;LUPININE;(-)-LUPININE;LUPININE HCL(P);(-)-Lupinine,97%;OCTAHYDRO-1H-QUINOLIZIN-1-METHANOL;[(1R,9aR)-quinolizidin-1-yl]methanol;(1R,9AR)-OCTAHYDRO-2H-QUINOLIZIN-1-YLMETHANOL;(1R-TRANS)-OCTAHYDRO-2H-QUINOLIZINE-1-METHANOL;((1R,9aR)-Octahydro-1H-quinolizin-1-yl)Methanol
CBNumber:
CB4409360
Summenformel:
C10H19NO
Molgewicht:
169.26
MOL-Datei:
486-70-4.mol

Lupinin Eigenschaften

Schmelzpunkt:
62-65°C
Siedepunkt:
160-164°C 4mm
alpha 
D26 -25.9° (c = 3 in water); D28 -21° (c = 9.5 in alcohol)
Dichte
0.9660 (rough estimate)
Brechungsindex
1.4610 (estimate)
Flammpunkt:
160-164°C/4mm
storage temp. 
Sealed in dry,Room Temperature
pka
14.90±0.10(Predicted)
Merck 
14,5609
BRN 
80447
CAS Datenbank
486-70-4(CAS DataBase Reference)
NIST chemische Informationen
2H-quinolizine-1-methanol, octahydro-, (1r-trans)-(486-70-4)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xi
R-Sätze: 20/21/22-41
S-Sätze: 22-36/37-39-26
RIDADR  1544
RTECS-Nr. OK5802000
Hazard Note  Irritant
HazardClass  6.1
PackingGroup  III
Bildanzeige (GHS)
Alarmwort
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
H312 Gesundheitsschädlich bei Hautkontakt. Akute Toxizität dermal Kategorie 4 Warnung P280,P302+P352, P312, P322, P363,P501
H332 Gesundheitsschädlich bei Einatmen. Akute Toxizität inhalativ Kategorie 4 Warnung P261, P271, P304+P340, P312
Sicherheit
P261 Einatmen von Staub vermeiden.
P321 Besondere Behandlung
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.

Lupinin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

S-Sätze Betriebsanweisung:

S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.

Beschreibung

This lupin alkaloid was first obtained by Baumert and is present in numerous plants of the Lupinus family, the most important sources being L. luteus, L. niger and L. palmeri Wats. It crystallizes from light petroleum in colourless rhombs and may be boiled without decomposition in a stream of hydrogen. It is laevorotatory with [α]17D - 20.35° (EtOH) and is soluble in H20 and most organic solvents but only sparingly so in petroleum ether. It is a sufficiently strong base to liberate ammonia from its salts. The hydrochloride forms colourless rhombic crystals from aqueous EtOH, m.p. 2l2-3°C; [α]D - 14° (H20); the hydriodide has m.p. 140-1 DC; aurichloride, m.p. 211-3°C; platinichloride as yellow crystals, m.p. 166-166.5°C; (+)-tartrate, m.p. 171°C; [α]D + 15.5° (EtOH); methochloride, m.p. 212-3°C; methiodide, m.p. 295-6°C; phenylurethane, m.p. 98-9°C; (-)-camphorsulphonate, m.p. 184°C; [α]D - 15.3° and the (+)-camphorsulphonate, m.p. 182-3°C; [α]D + 22.5°. The formation of a benzoyl derivative, m.p. 49-S00 C, oxidation of the alkaloid to lupininic acid, C9H16.COOH, m.p. 255°C and dehydration to anhydrolupinine, ClOH17N, a colourless oil of unpleasant odour, b.p. 216-7°C/726 mm all show the presence of a primary alcoholic hydroxyl group. Lupinine does not contain a methylimino group and behaves as a tertiary base. On exhaustive methylation it gives, in three stages, trimethylamine and an unsaturated alcohol. From this, it may be deduced that the alkaloid contains a bicyc1ic system. Several unsuccessful attempts were made to synthesize the alkaloid before this was finally achieved by Clemo and his co-workers.
This alkaloid, like the others of the lupinane group, is of little importance in medicine although the p-aminobenzoate has been shown to possess a marked local anaesthetic action.
The (+ )-form of the alkaloid has m.p. 68°C; [α]D + 19.9° and yields the (-)- tartrate, m.p.167-8°C; [α]D -15.8°.

Chemische Eigenschaften

Crystalline solid, obtained as orthorhombic prisms from acetone; melts at 69°C(156.2°F); bp 270°C (518°F); strongly basic;soluble in water and organic solvents.

Verwenden

The ι-form of lupinine occurs in seeds andherb of Lupinus luteous L., Chenopodiaceae,and other lupinus species. Its clinical applications are very limited.

Verwenden

antifeedant, antiinflammatory, oxytoxic

Health Hazard

This alkaloid is moderately toxic. The toxicaction, however, is lower than that of cytisine. Ingestion of high doses may producenausea, convulsions, and respiratory fail ure. The lethal dose in guinea pigs by theintraperitoneal route is 28 mg/kg..

Einzelnachweise

Baumert., Ber., 14, 1150, 1321, 1880, 1882 (1881)
Baumert., ibid, 15,631,1951 (1882)
Schmidt, Berend., Arch. Pharm., 235,263 (1897)
Willstiitter, Fourneau., Ber., 35, 1914 (1902)
Karrer et al., Helv. Chirn. Acta, 11, 1062 (1928)
Clemo, Raper, J. Chern. Soc., 1927 (1929)
Winterfeldt, Cosel., Arch. Pharrn., 70, 278 (1940)
Sadykov, Spasokukotski., J. Gen. Chern. USSR, 13,830 (1943)
Sadykov., ibid, 19,143 (1949)
Zaboev., ibid, 18,194 (1948)
Ratusky, Sorm., Chern. Listy., 47, 1491 (1953)

Lupinin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Lupinin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 77)Lieferanten
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Meryer (Shanghai) Chemical Technology Co., Ltd. 400-660-8290 21-61259100-
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486-70-4(Lupinin)Verwandte Suche:


  • (1R-TRANS)-OCTAHYDRO-2H-QUINOLIZINE-1-METHANOL
  • (1R,9AR)-1-(OCTAHYDRO-QUINOLIZIN-1-YL)-METHANOL
  • (1R,9AR)-OCTAHYDRO-2H-QUINOLIZIN-1-YLMETHANOL
  • 2H-Quinolizine-1-methanol, octahydro-, (1R-trans)-
  • (-)-Lupinine,97%
  • LUPININE HCL(P)
  • [1R,9aβ,(-)]-Octahydro-2H-quinolizine-1α-methanol
  • OCTAHYDRO-1H-QUINOLIZIN-1-METHANOL
  • [(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol
  • [(1R,9aR)-quinolizidin-1-yl]methanol
  • ((1R,9aR)-Octahydro-1H-quinolizin-1-yl)Methanol
  • LUPININ
  • (-)-LUPININE
  • LUPININE
  • 2H-Quinolizine-1-methanol, octahydro-, (1R,9aR)-
  • 486-70-4
  • 487-70-4
  • plantgrowth
  • Alkaloids
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