24316-19-6

Basic information

• Product Name: CEPHALOTAXINE
• Synonyms: (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-ol;CEPHALOTAXINE FROM CEPHALOTAXUS &;Cephalotaxin;[1S-(1a,3aS*,14b)]-1,5,6,8,9,14b-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol;NSC 128487;NSC 245454;(1S,3aR,14bβ)-1,5,6,8,9,14b-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1α-ol;(4R)-7,8-(Methylenebisoxy)-3,4-(trimethylene)-4β,5β-[(3S)-2-methoxy-3-hydroxypropene-1,3-diyl]-1,2,4,5-tetrahydro-3H-3-benzoazepine
• CAS NO: 24316-19-6
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36
• Product Categories: Alkaloids;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 24316-19-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 131-132 °C(Solv: benzene (71-43-2))
• Boiling Point: 495.2 °C at 760 mmHg
• Flash Point: 253.3 °C
• Appearance: White powder with faint yellow cast
• Density: 1.38 g/cm³
• Vapor Pressure: 1.27E-10mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: 2-8°C
• PKA: 13.30±0.40(Predicted)
• CAS DataBase Reference: CEPHALOTAXINE(CAS DataBase Reference)
• NIST Chemistry Reference: CEPHALOTAXINE(24316-19-6)
• EPA Substance Registry System: CEPHALOTAXINE(24316-19-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: UN 1544 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 24316-19-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Antiviral and antitumor agent

Definition

ChEBI: A benzazepine alkaloid isolated from Cephalotaxus harringtonia.

InChI:InChI=1/C18H21NO4/c1-21-15-9-18-4-2-5-19(18)6-3-11-7-13-14(23-10-22-13)8-12(11)16(18)17(15)20/h7-9,16-17,20H,2-6,10H2,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 84395-19-7 Methyl 3-carbocephalotaxyl-3-hydroxy-7-oxooctanoate 
• 38750-57-1 (±)-cephalotaxinone 

Downstream Products

• 61568-68-1 (3aR)-1t-benzoyloxy-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]azepine 
• 61568-71-6 (3aR)-1t-benzyloxycarbonyloxy-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]azepine 
• 38750-57-1 cephalotaxinone 
• 1040272-38-5 (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate 
• 1040272-14-7 1-((1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl) 4-methyl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-2-hydroxysuccinate 
• 36804-95-2 deoxyharringtonine 
• 52729-50-7 epi-deoxyharringtonine 
• 54086-27-0 (3-methyl-butyl)-butenedioic 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

ANALOGUES AND DERIVATIVES OF CEPHALOTAXINE AND METHODS FOR MAKING AND USING THE COMPOUNDS

Disclosed herein are embodiments of a compound having a Formula I, or a salt, solvate, N-oxide, prodrug, diastereomer or enantiomer thereof. Also disclosed are derivative compounds made from the compound of Formula I. Certain derivative compounds have a Formula V-2, or a salt, solvate, N-oxide, prodrug, diastereomer or enantiomer thereoAlso disclosed are method for making and using the disclosed compounds. Certain disclosed embodiments are useful for treating and/or preventing certain diseases and/or disorders, including proliferation diseases, such as leukemia.

Studies in Cephalotaxus Alkaloids. Stereospecific Total Synthesis of Homoharringtonine

The alkaloid ester homoharringtonine (2) was synthesized stereospecifically via the Reformatsky reaction of methyl α-bromoacetate with cephalotaxyl pyruvate (16) obtained by esterification of cephalotaxine with acid chloride derived from 15.The preparations of 2 and its unsaturated derivative 13 are described in detail.Possible explanations of the steric requirements in the esterification of cephalotaxine and of the steric outcome of the Reformatsky reaction leading to 2 and 13 are advanced.