27-DEOXYACTEIN Chemical Properties

Melting point:

253～254℃

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Hygroscopic, -20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly), Methanol (Very Slightly), Pyridine (Slightly)

form 

Solid

pka

13.03±0.70(Predicted)

color 

White to Off-White

Stability:

Hygroscopic

Major Application

pharmaceutical (small molecule)

InChIKey

GCMGJWLOGKSUGX-RBKCHLQLSA-N

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

27-DEOXYACTEIN Usage And Synthesis

Description

23-epi-26-Deoxyactein is a triterpene glycoside and a major constituent of black cohosh (C. racemosa). It reduces intracellular calcium concentrations, collapse of the mitochondrial membrane potential, production of reactive oxygen species (ROS), and cardiolipin peroxidation and inhibits autophagy and apoptosis in osteoblastic MC3T3-E1 cells induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). 23-epi-26-Deoxyactein (0.01-10 μM) reduces production of ROS and IL-1β and cell death induced by methylglyoxal in RIN-m5F β-cells.

Uses

27-Deoxyactein has shown stimulation of osteoblast function and inhibits bone resorbing mediators in the treatment of osteoporosis. It is a derivative of Actein (A191800), a gamma secretase modulators derived from botanicals.

Definition

ChEBI: 26-Deoxyactein is a triterpenoid. It has a role as a metabolite.

Synthesis

Compounds (20R, 24R)-24,25-16,23-23,27-trioxo-12-acetoxy-9. 19-cyclolanostane-3-O-??-D-xylopyranoside was prepared by taking the dried rhizome of Asclepiadaceae Cimicifuga foetida L., pulverized After extracted with 80% methanol aqueous solution at 90 ?? reflux 3 times, the extract to remove most of the methanol, respectively, with petroleum ether, chloroform, n-butanol extraction; recovery of solvents, petroleum ether part, chloroform part, n-butanol part; chloroform part of the mixing of silica gel samples, silica gel chromatography; chloroform: methanol gradient eluted with 1: 0, 40:1, 20: 1, 10: 1, the same portion of the TLC combined to obtain four fractions of Fr. A-D; Fr.B was separated by chromatography at atmospheric pressure on a silica gel column with a 40:1 chloroform:methanol gradient elution, and the compounds (20R, 24R)-24, 25-16, 23-, 23-27-trioxirane were obtained by repeated elution with 40:1 chloroform:methanol. 23,27-trioxo-12-acetoxy-9,19-cyclolanostane-3-O- ?? -D-Xylopyranoside. C37H56O10, colorless needle crystal, mp 253-254??C, [??]D = -61.2?? (c = 0.255, CHCl3-CH3OH (1:1)).

References

[1] KWANG SIK SUH. 27-Deoxyactein prevents 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cellular damage in MC3T3-E1 osteoblastic cells.[J]. Journal of Environmental Science and Health Part A-toxic\/hazardous Substances & Environmental Engineering, 2018, 53 6: 561-570. DOI: 10.1080/10934529.2018.1428275
[2] KWANG SIK SUH. Deoxyactein protects pancreatic β-cells against methylglyoxal-induced oxidative cell damage by the upregulation of mitochondrial biogenesis.[J]. International journal of molecular medicine, 2017, 40 2: 539-548. DOI: 10.3892/ijmm.2017.3018

27-DEOXYACTEIN(264624-38-6)Related Product Information

• CIMICIFUGOSIDE M
• CIMICIFUGOSIDE
• 3,4-Epoxytetrahydrofuran
• TRIDECYL GLYCIDYL ETHER
• 27-DEOXYACTEIN
• CYCLOARTANOL
• 1,2-EPOXYEICOSANE
• ISONOMETAL 3993 P
• LAURYL GLYCIDYL ETHER
• CYCLOARTANE
• GLYCIDYL HEXADECYL ETHER
• (R)-(+)-2,3-EPOXYPROPYL HEXYL ETHER
• (R)-(+)-GLYCIDYL UNDECYL ETHER, 97
• Actein
• DEOXYACTEIN, 27-(23-EPI-26-DEOXYACTEIN)(AHP)
• 2'-O-acetyl-27-deoxyactein
• TRANS,TRANS-4''-PENTYL-4-ETHOXY-BICYCLOHEXYL
• 2-[(cyclopentyloxy)methyl]oxirane