79-58-3 Usage
Description
First isolated by Wright and Luff from Veratrum album and V. viride, the original formula of C26H4302N was altered by Jacobs and Craig to that given
above. The base crystallizes from aqueous EtOH or Me2CO as the monohydrate.
It has [α]D + 19° (EtOH) and is a tertiary base, both oxygen atoms being in the
form of non-phenolic hydroxyl groups. The hydrobromide has m.p. 265-270°C;
the hydriodide, m.p. 293-6°C (26l-2°C); the diacetyl derivative has m.p.
l60-3°C and the p-bromobenzoyl compound melts at 254-6°C (dec.). On
catalytic hydrogenation it yields the dihydro derivative, m.p. 222°C from which
a diacetyl compound, m.p. 2l6-9°C may be prepared.
Selenium dehydrogenation of the base at 340°C furnishes 5-methyl-2-
ethylpyridine and a high proportion of a hydrocarbon, C18H16, m.p. 74-7°C
which yields a picrate, m.p. 131-2°C and a syrn-trinitrobenzene additive
compound, m.p. l44-5°C. The alkaloid undergoes the usual sterol reactions,
e.g. the Oppenauer process gives a ketone, rubijervone, m.p. 205-9°C; [α]30D +
100° (EtOH) which is reduced by sodium isopropoxide to the corresponding
epimeric alcohols. The earlier structure has been revised to 22G'H, 25{3H-solanid-
5-en-3{3,12G'-diol.
Purification Methods
Rubijervine crystallises from 95% EtOH as colourless rods. It has solvent of crystallisation and is dried at 120o/2mm. It is precipitated by digitonin. The hydrobromide crystallises from MeOH/Me2CO with m 265-270o(dec). The diacetate crystallises from MeOH with m 160-163o. The 3-benzoate gives colourless prisms from *C6H6 with m 156-159o and [] D 27.5 +22o (c 1.6, CHCl3). [Pelletier & Locke J Am Chem Soc 79 4531 1957, Jacobs & Craig J Biol Chem 148 41 1943, Beilstein 21 III/IV 2310.]
References
Poethke., Arch. Pharrn., 276, 170 (1938)
Jacobs, Craig.,J. Bioi. Chern., 148,41 (1943)
Jacobs, Craig., ibid, 149,451 (1943)
Jacobs, Craig., ibid, 159, 617 (1945)
Jacobs, Craig., ibid, 160,555 (1945)
Sato, Jacobs., ibid, 179,623 (1949)
Stereochemistry:
Hohne et al., Tetrahedron, 22,673 (1966)
Check Digit Verification of cas no
The CAS Registry Mumber 79-58-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 79-58:
(4*7)+(3*9)+(2*5)+(1*8)=73
73 % 10 = 3
So 79-58-3 is a valid CAS Registry Number.
InChI:InChI=1/C27H43NO2/c1-15-5-8-22-16(2)25-23(28(22)14-15)12-21-19-7-6-17-11-18(29)9-10-26(17,3)20(19)13-24(30)27(21,25)4/h6,15-16,18-25,29-30H,5,7-14H2,1-4H3/t15-,16+,18-,19+,20-,21?,22+,23-,24-,25-,26-,27+/m0/s1
79-58-3Relevant articles and documents
Compounds and compositions for treating infection
-
, (2009/04/24)
Compounds from 14 Kenyan plants, including from the root of Dovyalis abyssinica and Clutia robusta have been characterized and isolated, and their uses are disclosed.
