123834-18-4

Basic information

• Product Name: Brn 0072480
• Synonyms: 16-Epipyroaconitine;16-Epi-pyroaconitine;Aconitan-15-one, 14-(benzoyloxy)-3,13-dihydroxy-20-ethyl-4-(methoxymethyl)-1,6,16-trimethoxy-,(1-alpha,3-alpha,6-alpha,14-alpha,16-alpha)-;Brn 0072480
• CAS NO: 123834-18-4
• Molecular Formula: C32H43NO9
• Molecular Weight: 585.68512
• Mol File: 123834-18-4.mol

Chemical Properties

• Boiling Point: 692.4°Cat760mmHg
• Flash Point: 372.5°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 4E-20mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: Brn 0072480(CAS DataBase Reference)
• NIST Chemistry Reference: Brn 0072480(123834-18-4)
• EPA Substance Registry System: Brn 0072480(123834-18-4)

Safety Data

• Hazardous Substances Data: 123834-18-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C32H43NO9/c1-6-33-14-30(15-38-2)18(34)12-19(39-3)32-17-13-31(37)27(42-29(36)16-10-8-7-9-11-16)20(17)21(23(35)28(31)41-5)22(26(32)33)24(40-4)25(30)32/h7-11,17-22,24-28,34,37H,6,12-15H2,1-5H3/t17-,18+,19-,20-,21-,22?,24-,25+,26?,27+,28+,30-,31-,32?/m0/s1

Upstream product

• 302-27-2 acotinine 
• 639-24-7 C₃₄H₄₅NO₁₁ 
• 302-27-2 indaconitine 

Relevant articles and documents

Effect of pH on the metabolism of aconitine under rat intestinal bacteria and analysis of metabolites using HPLC/MS-MSn technique

A semi-quantitative method of mass spectrometry (MS) has been described for the analysis of metabolites of aconitine by rat intestinal bacteria at different pH. At pH 7.0, the rat intestinal bacteria exhibit optimal activity for the metabolism of aconitine. A high-performance liquid chromatography- electrospray ionization multiple-stage mass spectrometry (HPLC/ESI-MS n) method has been applied to investigate the characteristic product ions of metabolites. Then, the logical fragmentation pathways of metabolites have been proposed. By comparing the retention time (tR) of HPLC and the ESI-MSn data with the data of standard compounds and reports from literature, ten metabolites have been identified and a distinctive metabolite (15-deoxyaconitine) has been deduced first time. The experimental results demonstrate that HPLC/ESI-MSn is a specific and useful method for the identification of metabolites of aconitine. Also, in the present paper, the HPLC-MS method was introduced to determine the synthetical metabolite prior to the study of the toxicity by the method of Bliss. HPLC chromatogram of metabolites of aconitine at pH 7. 1. benzoylaconine, 2. 15-deoxybenzoylaconine, 3. 8-octenoyl-benzoylaconine, 4. 10-OH-aconitine, 5. 15-deoxyaconine, 6. aconitine, 7. 8-hexenoyl-benzoylaconine, 8. 8-propionyl-benzoylaconine, 9. 8-butyryl-benzoylaconine, 10. deoxyaconitine, 11. 8(3-hydroxyl)-butyryl- benzoylaconine.

Studies on the relative reactivity of three hydroxyl groups in aconitine

The relative reactivity of three hydroxyl groups in aconitine toward acetylation, chlorination, sulfonylation, and oxidation has been studied in this paper. The reduction of C-3 ketone and C-15 ketone derivatives of aconitine was also investigated. It was found that (1) the relative reactivity of three hydroxyl groups toward acetylation, chlorination, and sulfonylation is 3-OH>13-OH>>15-OH; (2) 3-OH is much more reactive than 15-OH toward oxidation; and (3) reduction of the carbonyl group at C-3 with NaBH4 generated a pair of C-3 epimers, while the reduction products of the carbonyl group at C-15 depend largely on the specific reducing agent and the absolute configuration of 16-OCH3. When the substrate has 16-OCH3, its carbonyl group at C-15 can be reduced with NaBH4 to yield exclusively the 15-OH-containing product. Upon replacement of reducing agent NaBH4 with LiAlH4, the C-15 carbonyl group can be reduced to yield a pair of C-15 epimers. On the other hand, when the substrate has 16-OCH3, C-15 carbonyl group can only be reduced to generate 15-OH-containing product.