37921-38-3

Basic information

• Product Name: Cimifugin
• Synonyms: CIMIFUGIN(P);(2S)-7-(Hydroxymethyl)-2-(2-hydroxypropan-2-yl)-4-methoxy-2,3-dihydrofuro[3,2-g]chromen-5-one;Cimifugin;(S)-2,3-Dihydro-7-(hydroxymethyl)-2-(1-hydroxy-1-methylethyl)-4-methoxy-5H-furo[3,2-g][1]benzopyran-5-one;CiMitin;Cimifugin, 98%, from Saposhnikovia divaricata (Turcz.) Schischk.
• CAS NO: 37921-38-3
• Molecular Formula: C16H18O6
• Molecular Weight: 306.32
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 37921-38-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 107～109℃
• Boiling Point: 546.4 °C at 760 mmHg
• Flash Point: 204.9 °C
• Appearance: /
• Density: 1.361 g/cm³
• Vapor Pressure: 8.98E-13mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: -20°C
• PKA: 14.25±0.29(Predicted)
• CAS DataBase Reference: Cimifugin(CAS DataBase Reference)
• NIST Chemistry Reference: Cimifugin(37921-38-3)
• EPA Substance Registry System: Cimifugin(37921-38-3)

Safety Data

• Hazardous Substances Data: 37921-38-3(Hazardous Substances Data)

Usage

Components

The main components of Cimicifuga are triterpenoid polyoxygenates, chromogen ketones, phenolic acids, various chromones, odontoamol and odontoamicin. Among them, the identified structures are: isoferulic acid, 3-acetyl caffeic acid, caffeic ester glucoside, cimifugin, cimifugin glucoside, 6-isoxanthine nucleoside, cimidahurine, cimidahurinie, D-glucose, sucrose, etc.

InChI:InChI=1/C16H18O6/c1-16(2,19)13-5-9-11(22-13)6-12-14(15(9)20-3)10(18)4-8(7-17)21-12/h4,6,13,17,19H,5,7H2,1-3H3

Upstream product

• 80681-45-4 Prim-O-Glucosylcimifugin 
• 80681-47-6 Acetic acid 1-[(S)-4-methoxy-5-oxo-7-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,3-dihydro-5H-furo[3,2-g]chromen-2-yl]-1-methyl-ethyl ester 

Relevant articles and documents

Biotransformation of prim-O-glucosylcimifugin by human intestinal flora and its inhibition on NO production and DPPH free radical

prim-O-Glucosylcimifugin (PGCN), a highest content chromone in the roots of Saposhnikovia divaricata, was incubated with human intestinal flora (HIF), and two biotransformation products were obtained from the incubated solution by chromatographic methods. The chemical structures of the two biotransformation products were elucidated as cimifugin (CN) and 5-O-methylvisamminol (MVL), respectively, on the basis of NMR and MS data. The biotransformation product CN was formed through a deglucosylation of PGCN by -glucosidase secreted from the HIF, and then the hydroxymethyl group of CN was reduced to lead to occurrence of MVL. All of these compounds were evaluated for their effect on the inhibition of nitric oxide production induced by lipopolysaccharide in macrophage cell line RAW 264.7 and for 1,1-diphenyl-2-picrylhydrazyl free-radical scavenging activity in cell-free bioassay system.

CHEMICAL STUDIES OF ANGELICA JAPONICA A. GRAY. I. ON THE CONSTITUENTS OF THE ETHYL ACETATE EXTRACT OF THE ROOT

The dried roots of Angelica japonica A.Gray (Umbelliferae) afforded three new chromones (VI, VIII and IX) together with six known chromones (I-V and VII) and fourteen known coumarins (X-XXIII) which were identified by comparison with authentic samples.The structure of VI, VIII and IX were established as (3S)-2,2-dimethyl-3,5-dihydroxy-8-hydroxymethyl-3,4-dihydro-2H,6H-benzodipyran-6-one, (3S)-2,2-dimethyl-3-β-D-glucosyloxy-5-hydroxy-8-methyl-3,4-dihydro-2H,6H-benzodipyran-6-one (sec-O-glucosylhamaudol) and (2S)-2-(1-hydroxy-1-methylethyl)-4-methoxy-7-β-D-glucosyloxymethyl-2,3-dihydro-5H-furobenzopyran-5-one (prim-O-glucosylcimifugin).Keywords: - Angelica japonica; chromone; coumarin; dihydropyranochromone; dihydrofurochromone; sec-O-glucosylhamaudol; prim-O-glucosylcimifugin