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479-98-1

Basic Information
CAS No.: 479-98-1
Name: Aucubin
Article Data: 7
Cas Database
Molecular Structure:
Molecular Structure of 479-98-1 (Aucubin)
Formula: C15H22O9
Molecular Weight: 346.334
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;
EINECS: 207-540-8
Density: 1.614 g/cm3
Melting Point: 180 - 184oC
Boiling Point: 669.025 °C at 760 mmHg
Flash Point: 358.414 °C
Solubility: Soluble in water, ethanol and methanol, hardly soluble in chloroform, ether and petroleum ether
Appearance: white crystal
Hazard Symbols: N/A
Risk Codes: 22
Safety: 22-45
Transport Information: N/A
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
ConditionsYield
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
ConditionsYield
With sodium tetrahydroborate In ethanol at 95℃; for 0.166667h; Yield given. Yields of byproduct given;

2'-O-benzoylaucubin

479-98-1

aucubin

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature;0.2 g
11044-25-0

hexa-O-acetyl-aucubin

479-98-1

aucubin

Conditions
ConditionsYield
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
ConditionsYield
With sodium methylate In methanol at 22℃; for 1h;
479-98-1

aucubin

tetrahydro-aucubin

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol100%
479-98-1

aucubin

77-76-9

2,2-dimethoxy-propane

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

Conditions
ConditionsYield
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
ConditionsYield
With pyridine; dmap at 20℃; for 168000h; Acylation;90%
With pyr76%
With pyridine; dmap In dichloromethane at 20℃; for 96h; Inert atmosphere;
479-98-1

aucubin

C15H20O9

Conditions
ConditionsYield
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+); acetone at 65℃; for 1h; Inert atmosphere; Sealed tube;87%
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  • Aucubin CAS 479-98-1

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    479-98-1

    Aucubin CAS 479-98-1

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  • Aucubin

  • Casno:

    479-98-1

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  • hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside

  • Casno:

    479-98-1

    hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside

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  • 479-98-1

  • Casno:

    479-98-1

    479-98-1

    Min.Order: 0

    FOB Price:  USD $ 0.0-0.0/

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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