26833-85-2

Basic information

• Product Name: HARRINGTONINE
• Synonyms: (3(r))-ter;4-methyl-cephalotaxin2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate(es;alkaloidcfromcephalotaxus;cephalotaxine,4-methyl(2r)-2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioat;nsc124147;HARRINGTONIN;HARRINGTONINE;HT
• CAS NO: 26833-85-2
• Molecular Formula: C28H37NO9
• Molecular Weight: 531.59
• Product Categories: Alkaloids;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 26833-85-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 73～75℃
• Boiling Point: 679.419 °C at 760 mmHg
• Flash Point: 364.7 °C
• Appearance: white solid
• Density: 1.35 g/cm³
• Vapor Pressure: 2.17E-19mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: 2-8°C
• PKA: 11.62±0.29(Predicted)
• CAS DataBase Reference: HARRINGTONINE(CAS DataBase Reference)
• NIST Chemistry Reference: HARRINGTONINE(26833-85-2)
• EPA Substance Registry System: HARRINGTONINE(26833-85-2)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 26833-85-2(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 26833-85-2 differently. You can refer to the following data:
1. The full structure of harringtonine has now been established from a study of the hydrolysis products of this base.
2. Harringtonine is a natural alkaloid that inhibits protein synthesis at low micromolar concentrations. It immobilizes ribosomes immediately after the initiation of translation. While harringtonine has drawn some interest in mitigating cancer, its homolog homoharrington is more effective, particularly for chronic myelogenous leukemia. The ability of harringtonine to immobilize initiating ribosomes can be used to capture ribosome-protected mRNA fragments for evaluating translation.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 26833-85-2 differently. You can refer to the following data:
1. specific anti-leukemia drug
2. A natural product with significant antitumor activities.

References

Mikolajczak, Powell, Smith, Tetrahedron, 28, 1995 (1972) Kelly, McKenna, Christenson, Tetrahedron Lett., 35m (1973)

InChI:InChI=1/C28H37NO9/c1-26(2,32)8-9-28(33,15-22(30)35-4)25(31)38-24-21(34-3)14-27-7-5-10-29(27)11-6-17-12-19-20(37-16-36-19)13-18(17)23(24)27/h12-14,23-24,32-33H,5-11,15-16H2,1-4H3/t23-,24-,27+,28-/m1/s1

Upstream product

• 24316-19-6 cephalotaxine 
• 68423-51-8 (Ξ)-4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carboxylic acid (3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl ester 
• 68423-50-7 4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carbonyl chloride 
• 68423-52-9 (Ξ)-2-benzyloxy-2-(3-hydroxy-3-methyl-butyl)-succinic acid 1-((3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester 

Relevant articles and documents

Synthesis method and intermediate of ester derivative of (-)-cephalotaxine

The invention discloses a synthesis method and an intermediate of an ester derivative of (-)-cephalotaxine. The synthesis method is characterized in that a compound A and a compound 4 undergoes a condensation reaction shown in the description in a solvent under the action of a condensing agent in order to obtain a compound I. The synthetic method utilizes an esterification reaction of a racemic epoxy branched-chain compound and the (-)-cephalotaxine to highly selectively obtain the chiral compound close to a single configuration, so the method has the advantages of simple and mild synthesis route, and easiness in industrialization.

Preparation of harringtonine from cephalotaxine

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