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Name |
Aucubin |
EINECS | 207-540-8 |
CAS No. | 479-98-1 | Density | 1.614 g/cm3 |
PSA | 149.07000 | LogP | -2.80150 |
Solubility | Soluble in water, ethanol and methanol, hardly soluble in chloroform, ether and petroleum ether | Melting Point |
180 - 184oC |
Formula | C15H22O9 | Boiling Point | 669.025 °C at 760 mmHg |
Molecular Weight | 346.334 | Flash Point | 358.414 °C |
Transport Information | N/A | Appearance | white crystal |
Safety | 22-45 | Risk Codes | 22 |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
Aucubin(6CI,7CI,8CI);β-D-Glucopyranoside,1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl, [1S-(1a,4aa,5a,7aa)]-;Aucubine;Aucubosid;Aucuboside;Rhimantin;β-D-Glucopyranoside,(1S,4aR,5S,7aS)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl; |
Article Data | 7 |
aucubin
Conditions | Yield |
---|---|
With potassium cyanide In methanol; dichloromethane at 20℃; for 7h; | A 45% B 519 mg |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 95℃; for 0.166667h; Yield given. Yields of byproduct given; |
aucubin
Conditions | Yield |
---|---|
With sodium hydroxide Ambient temperature; | 0.2 g |
hexa-O-acetyl-aucubin
aucubin
Conditions | Yield |
---|---|
With sodium methylate In methanol | |
Multi-step reaction with 3 steps 1: aq H2SO4 / dioxane / 24 h / 40 °C 2: Jones-reagent / acetone / 0.17 h / 0 - 5 °C 3: NaBH4 / ethanol / 0.17 h / 95 °C View Scheme |
Conditions | Yield |
---|---|
With sodium methylate In methanol at 22℃; for 1h; |
aucubin
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol | 100% |
Conditions | Yield |
---|---|
Stage #1: aucubin; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate; copper(II) sulfate In acetone at 0 - 5℃; for 96h; Substitution; Stage #2: With hydrogen; triethylamine; palladium on activated charcoal In methanol for 24h; Hydrogenation; Stage #3: With acetic acid In tetrahydrofuran for 48h; Hydrolysis; | 90% |
pivaloyl chloride
aucubin
(1S,4aR,5S,7aS)-5-(2,2-dimethyl-1-oxopropoxy)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 168000h; Acylation; | 90% |
With pyr | 76% |
With pyridine; dmap In dichloromethane at 20℃; for 96h; Inert atmosphere; |
aucubin
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+); acetone at 65℃; for 1h; Inert atmosphere; Sealed tube; | 87% |
The Aucubin, with the CAS registry number 479-98-1, is also known as β-D-Glucopyranoside,(1S,4aR,5S,7aS)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl. It belongs to the product categories of Iridoids; Natural Terpene Standards Chemical Class; Other Chemical Class; Oxygen containing Chemical Class; Alcohols; Alphabetic; AR to AZ Chromatography; Heterocyclics; Life Sciences Standards; Natural Compounds; Natural Compounds Chemical Class; Cytokine signaling. Its EINECS number is 207-540-8. This chemical's molecular formula is C15H22O9and molecular weight is 346.33. What's more, its IUPAC name is (2S,3R,4S,5S,6R)-2-[-(1S,4aR,5S,7aS-5-hydroxy-7-(hydroxymethyl-1,4a,5,7a-tetrahydrocyclopenta-[c]-pyran-1-yl]-oxy]-6-(hydroxymethyl)-oxane-3,4,5-triol. It should be sealed and stored in a ventilated and dry place. Moreover, it should be protected from oxides. Aucubin is an iridoid glycoside. It is found in plants used in traditional Chinese and folk medicine. It was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. This chemical is used in biochemical research.
Physical properties of Aucubin are: (1)ACD/LogP: -4.103; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -4.10; (4)ACD/LogD (pH 7.4): -4.10; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 9; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 149.07 Å2; (13)Index of Refraction: 1.66; (14)Molar Refractivity: 79.201 cm3; (15)Molar Volume: 214.644 cm3; (16)Polarizability: 31.398×10-24cm3; (17)Surface Tension: 88.64 dyne/cm; (18)Density: 1.614 g/cm3; (19)Flash Point: 358.414 °C; (20)Enthalpy of Vaporization: 112.525 kJ/mol; (21)Boiling Point: 669.025 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. You should not breathe dust. In case of accident or if you feel unwell, you need to seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: O2\C=C/[C@@H]1[C@@H](C(=C/[C@H]1O)\CO)[C@@H]2O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO
(2)Std. InChI: InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
(3)Std. InChIKey: RJWJHRPNHPHBRN-FKVJWERZSA-N