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522-47-4

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522-47-4 Usage

Description

This carboline alkaloid has been obtained from Lochnera rosea and is also present in curare (Strychnos toxifera). Early preparations have been designated Alkaloid 'C' and C-Alkaloid T. It has [α]D + 56° (pyridine) or + n° (EtOH) and forms a crystalline picrate with a double melting point of 177-9°C and 243-5°C (dec.). The methiodide is identical with lochneram iodide, m.p. 235-8°C. A characteristic p-toluenesulphonyl derivative has been prepared, m.p. 153-4°C. One primary alcoholic hydroxyl is present and the alkaloid yields the O-acetate as colourless needles, m.p. 243°C; [α]D - 5.6° ± 3.0° (c 0.36, pyridine). The structure is that of O-methylsarpagine.

References

Janot, LeMen., Cornpt. rend., 243, 1789 (1956) Mors et at., Chern. Ind., 173 (1956) Arnold et at., Helv. Chirn. Acta, 40, 705 (1957) Arnold et al., ibid, 41, 1505 (1958) Karrer et at., Angew. Chern., 70,644 (1958)

Check Digit Verification of cas no

The CAS Registry Mumber 522-47-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 2 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 522-47:
(5*5)+(4*2)+(3*2)+(2*4)+(1*7)=54
54 % 10 = 4
So 522-47-4 is a valid CAS Registry Number.
InChI:InChI=1/C20H24N2O2/c1-3-11-9-22-18-8-15-14-6-12(24-2)4-5-17(14)21-20(15)19(22)7-13(11)16(18)10-23/h3-6,13,16,18-19,21,23H,7-10H2,1-2H3/b11-3-/t13-,16+,18-,19-/m0/s1

522-47-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Lochnerine

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:522-47-4 SDS

522-47-4Downstream Products

522-47-4Relevant articles and documents

-

Yuldashev et al.

, (1966)

-

-

Khalmirzhaev et al.

, (1973)

-

Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P -(+)-dispegatrine and six other monomeric indole alkaloids

Edwankar, Chitra R.,Edwankar, Rahul V.,Namjoshi, Ojas A.,Liao, Xuebin,Cook, James M.

, p. 6471 - 6487 (2013/07/26)

The first regio- and stereocontrolled total synthesis of the bisphenolic, bisquaternary alkaloid (+)-dispegatrine (1) has been accomplished in an overall yield of 8.3% (12 reaction vessels) from 5-methoxy-d-tryptophan ethyl ester (17). A crucial late-stage thallium(III) mediated intermolecular oxidative dehydrodimerization was employed in the formation of the C9-C9′ biaryl axis in 1. The complete stereocontrol observed in this key biaryl coupling step is due to the asymmetric induction by the natural sarpagine configuration of the monomer lochnerine (6) and was confirmed by both the Suzuki and the oxidative dehydrodimerization model studies on the tetrahydro β-carboline (35). The axial chirality of the lochnerine dimer (40) and in turn dispegatrine (1) was established by X-ray crystallography and was determined to be P(S). Additionally, the first total synthesis of the monomeric indole alkaloids (+)-spegatrine (2), (+)-10-methoxyvellosimine (5), (+)-lochnerine (6), lochvinerine (7), (+)-sarpagine (8), and (+)-lochneram (11) were also achieved via the common pentacyclic intermediate 16.

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