Aucubin supplier | CasNO.479-98-1

Name
Aucubin
EINECS 207-540-8
CAS No. 479-98-1
Article Data7
CAS DataBase
Density 1.614 g/cm³
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
Appearance white crystal
Safety 22-45
Risk Codes 22
Molecular Structure
Hazard Symbols
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;
PSA 149.07000
LogP -2.80150

Synthetic route

: 479-98-1
aucubin

: 11044-25-0
hexa-O-acetyl-aucubin

A: 135743-80-5
6-O-acetyl-aucubin

B: 479-98-1
aucubin

Conditions

Conditions	Yield
With potassium cyanide In methanol; dichloromethane at 20℃; for 7h;	A 45% B 519 mg

: 82504-05-0
penta-O-acetyl-6-chetoaucubin

A: 82535-77-1
6-epi-aucubin

B: 479-98-1
aucubin

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 95℃; for 0.166667h; Yield given. Yields of byproduct given;

: 2'-O-benzoylaucubin

: 479-98-1
aucubin

Conditions

Conditions	Yield
With sodium hydroxide Ambient temperature;	0.2 g

: 11044-25-0
hexa-O-acetyl-aucubin

: 479-98-1
aucubin

Conditions

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

: acuminatuside

A: 2309-07-1
Methyl ferulate

B: 479-98-1
aucubin

Conditions

Conditions	Yield
With sodium methylate In methanol at 22℃; for 1h;

: 479-98-1
aucubin

: tetrahydro-aucubin

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	100%

: 479-98-1
aucubin

: 77-76-9
2,2-dimethoxy-propane

: 10β-4',6'-O-isopropylidene-3,4,7,8-tetrahydroaucubin

Conditions

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%

: 3282-30-2
pivaloyl chloride

: 479-98-1
aucubin

: 318267-52-6
(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

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;

: 479-98-1
aucubin

: C15H20O9

Conditions

Conditions	Yield
With 4-methyl-morpholine; 6C6H15P4CF3O3S(1-)2Ru(2+); acetone at 65℃; for 1h; Inert atmosphere; Sealed tube;	87%

: 479-98-1
aucubin

A: 31655-27-3
6,10-bisdeoxyaucubin

B: 63879-67-4
monodeoxyaucubin

Conditions

Conditions	Yield
With lithium In ammonia at -70℃; for 0.166667h;	A 10% B 80%

: 108-24-7
acetic anhydride

: 479-98-1
aucubin

: 18162-48-6
tert-butyldimethylsilyl chloride

A: 6,2',3',4',6'-penta-O-acetyl-10-O-tert-butyldimethylsilylaucubin

B: 2',3',4'-tri-O-acetyl-6,10,6'-tri-O-tert-butyldimethylsilylaucubin

C: 6,2',3',4'-tetra-O-acetyl-10,6'-di-O-tert-butyldimethylsilylaucubin

D: 6,10,2',3',4'-penta-O-acetyl-6'-O-tert-butyldimethylsilylaucubin

Conditions

Conditions	Yield
Stage #1: aucubin; tert-butyldimethylsilyl chloride With pyridine In dichloromethane at 0 - 20℃; for 1h; Stage #2: acetic anhydride With pyridine In dichloromethane at 20℃; for 24h; Further stages.;	A 1% B 16% C 63% D 1%

...Expand

: 479-98-1
aucubin

: 77-76-9
2,2-dimethoxy-propane

A: 256221-84-8
4',6'-O-isopropylidene-aucubin

B: 4',6'-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)aucubin

C: 4',6'-O-isopropylidene-6-O-(1-methyl-1-methoxyethyl)aucubin

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate; copper(II) sulfate In acetone at 0 - 5℃; for 96h; Substitution;	A 40% B n/a C n/a

...Expand

: 108-24-7
acetic anhydride

: 479-98-1
aucubin

: 11044-25-0
hexa-O-acetyl-aucubin

Conditions

Conditions	Yield
With pyridine at 20℃; for 1.5h;	30%

: 479-98-1
aucubin

: (1S,4aR,5S,7aS)-5-Hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-7-carbaldehyde

Conditions

Conditions	Yield
With manganese(IV) oxide In water; acetone for 48h; Ambient temperature;	8%

: 479-98-1
aucubin

A: 90646-36-9
(4aR)-1ξ-Hydroxy-7ξ-methyl-(4ar,7ac)-octahydro-cyclopenta[c]pyran

B: 91267-40-2
(4aR)-1ξ-ethoxy-7ξ-methyl-(4ar,7ac)-octahydro-cyclopenta[c]pyran

Conditions

Conditions	Yield
With sulfuric acid; platinum Hydrogenation;

: 67-56-1
methanol

: 479-98-1
aucubin

: 139013-62-0
(1S,4S,5S)-3,4-Bis-hydroxymethyl-5-((E)-2-methoxy-vinyl)-cyclopent-2-enol

Conditions

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate 1) MeOH, 20 min, 2) 0 - 5 deg C, 20 min; Yield given. Multistep reaction;

: 67-56-1
methanol

: 479-98-1
aucubin

A: 139013-62-0
(1S,4S,5S)-3,4-Bis-hydroxymethyl-5-((E)-2-methoxy-vinyl)-cyclopent-2-enol

B: 129715-16-8
(1R,2R)-3,4-Bis-hydroxymethyl-2-((E)-2-methoxy-vinyl)-cyclopent-3-enol

Conditions

Conditions	Yield
With sodium tetrahydroborate; methanolate; mercury(II) diacetate 1) MeOH, 20 min, 2) 20 min; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 67-56-1
methanol

: 479-98-1
aucubin

A: 139013-62-0
(1S,4S,5S)-3,4-Bis-hydroxymethyl-5-((E)-2-methoxy-vinyl)-cyclopent-2-enol

B: 129715-14-6
3,4-dihydro-3α-methoxyaucubin

Conditions

Conditions	Yield
With sodium tetrahydroborate; KH2PO4 buffer; mercury(II) diacetate 1) MeOH, 20 min, 2) 20 min; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

Aucubin Specification

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

Product Name

Aucubin

Synthetic route

Aucubin Specification

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