ELEUTHEROSIDE A Chemical Properties

Melting point:

283～286℃

Boiling point:

673.6±55.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

Flash point:

361℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly,Heated), Pyridine (Slightly, Sonicated)

pka

12.91±0.70(Predicted)

form 

Solid

color 

Off-White to Pale Beige

InChIKey

YITHQYDRZAVJHB-WWJUBMRMSA-N

LogP

8.615 (est)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29389090

Toxicity

LD50 intraperitoneal in mouse: 62mg/kg

ELEUTHEROSIDE A Usage And Synthesis

Uses

Daucosterol can be used as an efficient and inexpensive neuroprotectants, to which the IGF1-like activity of daucosterol contributes and it could be potentially developed as a medicine for ischemic stroke treatment. Moreover, daucosterol has neuroprotective activity, it has proliferation-enhancing activity of neural stem cells (NSCs), and it as an efficient and inexpensive growth factor alternative that could be potentially developed as a medicine for ischemic stroke treatment, can significantly reduce neuronal loss.
The study demonstrated that daucosterol works as an efficient and inexpensive growth factor alternative that could be used in clinical medicine and research applications.

Description

Daucosterol, alias: Citoside, β-Sitosterol β-D-glucoside, and the molecular formula is C35H6. The compound of the formula (description column) belongs to a carotene compound, which is present in mallow family plants, and figs and other plants also contain carotene. Daucosterol exhibits anti-tumor, anti-inflammatory and acaricidal activities, also moderate antibacterial activity against Bacillus subtilis and Staphylococcus aureus, and it has anti-cancer and apoptotic effects in human colon cancer cell line HCT-116.

Chemical Properties

White to off white powder

Uses

β-Sitosterol and β-sitosteryl-β-D-glucoside were isolated as analgesic constituents from the leaves of Mentha cordifolia Opiz.

Definition

ChEBI: A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruti osa.

Synthesis

β-sitosterol (124.4 g, 0.3 mol) and D-glucose (18.0 g, 0.1 mol) were dissolved in ethylbenzene (600 mL). Trimethylsilyl trifluoromethanesulfonate (TMSOTf, 8.9 g, 7.3 mL, 40 mmol) was slowly added to the reaction system at 80 °C and the reaction was continued at a constant temperature until thin-layer chromatography (TLC) detection showed that the D-glucose was almost completely consumed (about 15 h). Upon completion of the reaction, the reaction solution was concentrated and subsequently separated by silica gel column chromatography using dichloromethane as eluent (silica gel particle size 100-200 mesh). The separation was monitored by TLC until β-sitosterol was no longer detected in the eluate, and the corresponding eluate was collected and concentrated to give the recovered β-sitosterol (83.0 g, 0.2 mol). The elution was continued with ethyl acetate as eluent and monitored by TLC until the target product (2R,3R,4S,5S,6R)-2-((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3, 4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol. Concentration of the eluate containing the target product gave a white solid product (47.3 g) in 82% yield and 97.8% purity as determined by high performance liquid chromatography (HPLC).

in vivo

References

[1] Patent: CN104693266, 2018, B. Location in patent: Paragraph 0062-0064

ELEUTHEROSIDE A(474-58-8)Related Product Information

• 1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE
• SYRINGIN(SEE ELEUTHEROSIDE B)(P),Syrigin，Syrigin，Eleutheroside B,ELEUTHEROSIDE B,Ciwujianoside-B(ELEUTHEROSIDE B),Syringin (eleutheroside B)
• ELEUTHEROSIDE E
• ELEUTHEROSIDE E
• ELEUTHEROSIDE B1(RG)
• ELEUTHEROSIDE A
• BETA-SITOSTEROL
• ELEUTHEROSIDE E1,ELEUTHEROSIDE B+E
• Eleutheroside B (Syringin),ELEUTHEROSIDE B(P)
• beta-Sitosterol
• ELEUTHEROSIDE C
• Eleutheroside E (Syringaresinol diglucoside)
• ELEUTHEROSIDE A(SEE PART#19291)(P)
• EleutherosideⅠ
• Eleutheroside B1 7-Hydroxy-6,8-dimethoxycoumarin glucoside
• Eleutheroside K
• ELEUTHEROSIDE E1(P)
• ELEUTHEROSIDE KIT (SIBERIAN GINSENG)