57-22-7

Basic information

• Product Name: Vincristine
• Synonyms: VINCRISTINE;Vincaleukoblastine, 22-oxo-;LCR;Leucristine;Leurocristine (7CI, 8CI);Vincaleukoblastine, 22-oxo- (9CI);Vincristine (base and/or unspecified salts);Vincristine ,VCR, NSC-67574, Oncovin
• CAS NO: 57-22-7
• Molecular Formula: C46H56N4O10
• Molecular Weight: 824.96
• EINECS: 200-318-1
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 57-22-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 211-216 ºC
• Boiling Point: 761.92°C (rough estimate)
• Appearance: a white crystalline solid
• Density: 1.1539 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• PKA: 5.4(at 25℃)
• Stability: Stable, but may be heat sensitive. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Vincristine(CAS DataBase Reference)
• NIST Chemistry Reference: Vincristine(57-22-7)
• EPA Substance Registry System: Vincristine(57-22-7)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 57-22-7(Hazardous Substances Data)

Usage

Chemical Description

Vincristine is a hydrophobic antitumor drug used to treat various types of cancer.

InChI:InChI=1/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37?,38?,39-,42+,43-,44?,45+,46+/m1/s1

Synthetic route

vincristine sulfate (2068-78-2) → Vincristine (57-22-7)

Conditions	Yield
With sodium carbonate In methanol; chloroform; water	98%

cyclovincristine (101156-38-1) → Vincristine (57-22-7)

Conditions	Yield
With sodium tetrahydroborate In dichloromethane; acetic acid for 2h; Ambient temperature;	79%

anhydrovinblastine (38390-45-3, 56083-20-6, 61246-76-2, 105815-31-4) → Vincristine (57-22-7) + catharine + vinblastin (363623-08-9, 906333-70-8) + vinleurosine (23360-92-1)

Conditions	Yield
With cell-free extracts from Catharanthus roseus Product distribution; Mechanism; Ambient temperature; biosynthesis of the products were studied; experiment was performed with 3',4'-anhydrovinblastine and the incorporation of the radiolabel into the products were investigated;

Vincristine (57-22-7) → desacetylvincristine (3704-01-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; for 48h;	70%

bromomethyl 4-hydroxy-3-methoxystyryl ketone + Vincristine (57-22-7) → C57H67N4O13(1+)*Br(1-)

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	68%

Vincristine (57-22-7) → vincristine N'b-oxide

Conditions	Yield
Stage #1: Vincristine With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.0333333h; Stage #2: With sodium carbonate In dichloromethane; water	67%

C14H11BrO + Vincristine (57-22-7) → C60H67N4O11(1+)*Br(1-)

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	67%

C10H8BrClO (1392239-32-5) + Vincristine (57-22-7) → C56H66ClN4O11(1+)*Br(1-)

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	65%

trifluoromethylsulfonic anhydride (358-23-6) + C13H17N3O3 + Vincristine (57-22-7) → C59H72N7O12(1+)*CF3O3S(1-)

Conditions	Yield
Stage #1: trifluoromethylsulfonic anhydride; C13H17N3O3 With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 0.833333h; Inert atmosphere; Stage #2: Vincristine In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere;	57%

Vincristine (57-22-7) → cyclovincristine (101156-38-1)

Conditions	Yield
With chromium(VI) oxide; acetic anhydride In methanol; dichloromethane; acetic acid at -20℃; for 17h;	46%

Vincristine (57-22-7) → C46H55N5O12 + C46H55N5O12 + C46H55N5O12

Conditions	Yield
With nitric acid In chloroform; acetic acid at -20℃;	A 31 % Chromat. B 5 % Chromat. C 60 % Chromat.

Vincristine (57-22-7) → 4-(Boc-Gly)vincristine (1579248-61-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 48 h / 20 °C 2.1: triethylamine; isobutyl chloroformate / ethyl acetate / 0.5 h / -15 °C 2.2: -15 - 20 °C View Scheme

Upstream product

• 38390-45-3 anhydrovinblastine 
• 101156-38-1 cyclovincristine 
• 2068-78-2 vincristine sulfate 

Downstream Products

• 3704-01-6 desacetylvincristine 

Relevant articles and documents

Synthesis of vinca alkaloids and related compounds. Part XCIII. Skeletal rearrangement of cyclovinblastine derivatives: Formation of a novel bisindole system

Bisindole alkaloids of the vinblastine (VLB) type can be oxidized to give a Ψ-aspidosperma-aspidosperma type skeleton via 3'-7'-transannular cyclization. Acid catalysis triggers an aspidospermane→eburnane skeletal rearrangement of these cyclic derivatives, thus giving a novel bisindole system with a Ψ-eburnea-aspidosperma type skeleton. A previously unexplored aspect of this transformation is the observed retention or inversion at C(16') depending on the starting C(16') configuration. The present paper gives a detailed account of the synthetic aspect of this work together with preliminary NMR and CD results concerning the epimerization at C(16').

Biosynthesis of the indole alkaloids. Cell-free systems from Catharanthus roseus plants

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