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Anhydrovinblastine

$144

  • Brand : BIOFRON

  • Catalogue Number : BN-O1424

  • Specification : 95%(HPLC)

  • CAS number : 38390-45-3

  • Formula : C46H56N4O8

  • Molecular Weight : 792.96

  • PUBCHEM ID : 443324

  • Volume : 20mg

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Catalogue Number

BN-O1424

Analysis Method

HPLC,NMR,MS

Specification

95%(HPLC)

Storage

-20℃

Molecular Weight

792.96

Appearance

Powder

Botanical Source

This product is isolated and purified from the herbs of Catharanthus roseus (L.)G. Don

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCC1=CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC

Synonyms

Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(13S,15S)-17-ethyl-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0.0]nonadeca-4(12),5,7,9,16-pentaen-13-yl]-3-hydroxy-16-m ethoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate/aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(7S,9S)-5-ethyl-1,4,7,8,9,10-hexahydro-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2β,3β,4β,5α,12β,19α)-/Vincaleukoblastine, 3',4'-didehydro-4'-deoxy-6,7-dihydro-/Anhydrovinblastine/ANHYDROVINBLASTIN/Vinblastineanhydrous/3',4'-Dehydroisoleurosine/Vincaleukoblastine, 3',4'-didehydro-4'-deoxy-/Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(13S,15S)-17-ethyl-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0.0]nonadeca-4(12),5,7,9,16-pentaen-13-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate/3',4'-Dehydrovinblastine/Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(7S,9S)-5-ethyl-1,4,7,8,9,10-hexahydro-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3-hydroxy-16-methoxy-1-m ;ethyl-, methyl ester, (2β,3β,4β,5α,12β,19α)-/Anhydrovincaleukoblastine

IUPAC Name

methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S)-17-ethyl-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,16-pentaen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

Density

1.4±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

205-207ºC

InChl

InChI=1S/C46H56N4O8/c1-8-28-21-29-24-45(41(52)56-6,37-31(15-19-49(25-28)26-29)30-13-10-11-14-34(30)47-37)33-22-32-35(23-36(33)55-5)48(4)39-44(32)17-20-50-18-12-16-43(9-2,38(44)50)40(58-27(3)51)46(39,54)42(53)57-7/h10-14,16,21-23,29,38-40,47,54H,8-9,15,17-20,24-26H2,1-7H3/t29-,38+,39-,40-,43-,44-,45+,46+/m1/s1

InChl Key

FFRFGVHNKJYNOV-DOVUUNBWSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:38390-45-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31442047

Abstract

A new triarylaminium radical cation promoted coupling of catharanthine with vindoline is disclosed, enlisting tris(4-bromophenyl)aminium hexachlororantimonate (BAHA, 1.1 equiv) in aqueous 0.05 N HCl/trifluoroethanol (1-10:1) at room temperature (25 °C), that provides anhydrovinblastine in superb yield (85%) with complete control of the newly formed quaternary C16′ stereochemistry. A definition of the scope of aromatic substrates that participate with catharanthine in the BAHA-mediated diastereoselective coupling reaction and simplified indole substrates other than catharanthine that participate in the reaction are disclosed that identify the key structural features required for participation in the reaction, providing a generalized indole functionalization reaction that bears little structural relationship to catharanthine or vindoline.

Title

Triarylaminium Radical Cation Promoted Coupling of Catharanthine with Vindoline: Diastereospecific Synthesis of Anhydrovinblastine and Reaction Scope.

Author

Boon BA1, Boger DL1.

Publish date

2019 Sep 11

PMID

17970117

Abstract

A high performance liquid chromatographic (HPLC) method with gradient elution was developed for the simultaneous determination of vindoline, catharanthine and anhydrovinblastine in Catharanthus roseus. The analytes were separated on a Waters (5)C18-MS-II column (4.6 mm x 250 mm) and detected at 220 nm. The mobile phases were methanol-1% (v/v) diethylamine solution (adjusted to pH 7.3 with phosphate) for gradient elution at temperature of 25 degrees C. The calibration curves for vindoline, catharanthine and anhydrovinblastine showed good linearity in the ranges of 0.03-1 mg/mL (r = 0.9997), 0.03-1 mg/mL (r = 0.9999) and 0.01-0.5 mg/mL (r = 0.9986), respectively. The recoveries were 96.8%, 97.0%, and 96.4% and the relative standard deviations (RSDs) were 1.53%, 1.37%, and 1.96%. The method is accurate, rapid and simple for the determination of vindoline, catharanthine and anhydrovinblastine in Catharanthus roseus.

Title

[Simultaneous determination of vindoline, catharanthine and anhydrovinblastine in Catharanthus roseus by high performance liquid chromatography].

Author

Yang L1, Tang Z, Zu Y.

Publish date

2007 Jul

PMID

16651762

Abstract

Dimeric indole alkaloid, anhydrovinblastine, which can be obtained from catharanthine and vindoline in a high yield, was converted stereoselectively into vinblastine through alternating oxidation-reduction with oxygen and NaBH(3)CN in the presence of anti-vinblastine monoclonal antibody.

Title

Stereoselective conversion of anhydrovinblastine into vinblastine utilizing an anti-vinblastine monoclonal antibody as a chiral mould.

Author

Shirahama T1, Kohno T, Kaijima T, Nagaoka Y, Morimoto D, Hirata K, Uesato S.

Publish date

2006 May


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